- Metal-free oxidative cyclization of 2-amino-benzamides, 2-aminobenzenesulfonamide or 2-(aminomethyl)anilines with primary alcohols for the synthesis of quinazolinones and their analogues
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A general metal-free oxidative cyclization process has been developed for the synthesis of quinazolinones, benzothiadiazines and quinazolines. By this protocol, a range of substituted 2-aminobenzamides, 2-aminobenzenesulfonamide and 2-(aminomethyl)anilines react with various alcohols, leading to the desired annulated products smoothly. This protocol features many advantages as broad substrate scope, mild reaction conditions, low environmental pollution, high atom-economy and good to excellent yields.
- Sun, Jinwei,Tao, Tao,Xu, Dan,Cao, Hui,Kong, Qinggang,Wang, Xinyu,Liu, Yun,Zhao, Jianglin,Wang, Yi,Pan, Yi
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- Palladium Catalyzed Cross-Dehydrogenative Coupling/Annulation Reaction: A Practical and Efficient Approach to Hydroxyisoindolo[1,2-b]quinazolinone
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The palladium-catalyzed cross-dehydrogenative coupling (CDC) followed by an intramolecular cyclization between arylquinazolinones and aldehydes has been described. This viable transformation provides a variety of novel substituted hydroxyisoindolo[1,2-b]quinazolinone compounds in moderate to good yields. Additionally, the reaction is performed with toluene in place of benzaldehyde by using an excess amount of tert-butyl hydroperoxide (TBHP) as the oxidant in good yield.
- Dabiri, Minoo,Lehi, Noushin Farajinia,Movahed, Siyavash Kazemi,Khavasi, Hamid Reza
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- A recyclable CuO-catalyzed synthesis of 4(3H)-quinazolinones
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This paper describes the synthesis of 2-substituted and 2,3-disubstituted 4(3H)-quinazolinones via a tandem reaction involving anthranilamides and aromatic aldehydes catalyzed by 3 mol% CuO powder under air atmosphere. This new method has several advantages: it uses recyclable and cheap CuO powder as the catalyst and air as the green oxidant, water is the only byproduct, and the solvent is recycled. It is easy to run, has a high atom economy and good to excellent yields. A mechanism for the CuO-catalyzed synthesis of the 4(3H)-quinazolinones is proposed.
- Zhan, Dan,Li, Tianbin,Wei, Haidong,Weng, Wen,Ghandi, Khashayar,Zeng, Qingle
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- Synthesis and β-glucuronidase inhibitory activity of 2-arylquinazolin-4(3H)-ones
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2-Arylquinazolin-4(3H)-ones 1-25 were synthesized by reacting anthranilamide with various benzaldehydes using CuCl2·2H 2O as a catalyst in ethanol under reflux. Synthetic 2-arylquinazolin-4(3H)-ones 1-25 were evaluated for their β-glucuronidase inhibitory potential. A trend of inhibition IC50 against the enzyme in the range of 0.6-198.2 μM, was observed and compared with the standard d-saccharic acid 1,4-lactone (IC50 = 45.75 ± 2.16 μM). Compounds 13, 19, 4, 12, 14, 22, 23, 25, 15, 8, 17, 11, 21, 1, 3, 18, 9, 2, and 24 with the IC50 values within the range of 0.6-44.0 μM, indicated that the compounds have superior activity than the standard. The compounds showed no cytotoxic effects against PC-3 cells. A structure-activity relationship is established.
- Khan, Khalid Mohammed,Saad, Syed Muhammad,Shaikh, Nimra Naveed,Hussain, Shafqat,Fakhri, Muhammad Imran,Perveen, Shahnaz,Taha, Muhammad,Choudhary, Muhammad Iqbal
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- Cp2ZrCl2-catalyzed synthesis of 2-substituted quinozolin-4(3H)-ones
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Zirconocene dichloride (Cp2ZrCl2) in the presence of DMF was found to be a highly efficient catalyst for the synthesis of structurally diverse 2-substituted quinozolin-4(3H)-ones by reaction of anthranilimide with a wide range of aryl aldehydes. Copyright
- Jadhav, Jagannath,Khanapure, Sharanabasappa,Salunkhe, Rajashri,Rashinkar, Gajanan
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- Ligand-Free Copper-Manganese Spinel Oxide-Catalyzed Tandem One-Pot C–H Amidation and N-Arylation of Benzylamines: A Facile Access to 2-Arylquinazolin-4(3H)-ones
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An efficient ligand-free copper-manganese (Cu-Mn) spinel oxide-catalyzed direct tandem C?H oxygenation and N-arylation of benzylamines has been developed. The method has been utilized for the synthesis of medicinally important 2-arylquinazolin-4(3H)-ones. Salient features of this method include recyclable catalyst, no ligand, excellent product yields, shorter reaction times and a broad substrate scope. (Figure presented.).
- Sharma, Rohit,Vishwakarma, Ram A.,Bharate, Sandip B.
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- Site-Selective C–H Amidation of 2-Aryl Quinazolinones Using Nitrene Surrogates
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The site-selective modifications of quinazolinones constitute a pivotal topic in drug discovery and material science. Herein, we describe the rhodium(III)-catalyzed C–H amidation of 2-aryl quinazolin-4(3H)-ones with a range of nitrene surrogates including dioxazolones, organic azides, and N-methoxyamides. Complete site-selectivity and functional group tolerance are observed. Notably, the large-scale reaction and late-stage functionalization highlight the synthetic potential of the developed protocol. Combined mechanistic investigations elucidate a plausible reaction mechanism of this process.
- Kim, Saegun,Jeoung, Daeun,Kim, Kunyoung,Lee, Seok Beom,Lee, Suk Hun,Park, Min Seo,Ghosh, Prithwish,Mishra, Neeraj Kumar,Hong, Suckchang,Kim, In Su
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- Electron transfer-induced oxidation of 2,3-dihydroquinazolin-4(1H)-ones
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A series of 2-substituted 2,3-dihydroquinazolin- 4(1H)-ones were oxidized to quinazolin-4(3H)-ones using tetrabutylammonium peroxydisulfate. The rate and the outcome of the reaction are dependent on the type and nature of 2-substitution. An electron transfer mechanism is proposed for this study, which is supported by the retention or elimination of 2-substitution during the oxidation process.
- Memarian, Hamid Reza,Ghahremani, Saeideh
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- A novel method for the synthesis of 4(3H)-quinazolinones
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Condensation of anthranilamide with aryl, alkyl or heteroaryl aldehydes in refluxing ethanol and the presence of CuCl2 afforded the corresponding 2-substituted quinazolinones in excellent yields.
- Abdel-Jalil, Raid J.,Voelter, Wolfgang,Saeed, Muhammad
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- Q-Tube assisted MCRs for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones
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A Q-tube assisted, efficient method for the preparation of 2-phenylquinazolin-4-ones is here presented. The target structures were prepared through the one-pot, multicomponent reaction between isatoic anhydride, an aromatic aldehyde and a primary amine following a catalyst-free approach. The use of the commercially available Q-tube apparatus allowed to perform reactions at external temperature higher to the solvent boiling point generating medium pressure conditions, shortening the reaction times and affording good yields in all the example herein reported. Formula parented.
- Sancineto, Luca,Monti, Bonifacio,Merlino, Orsola,Rosati, Ornelio,Santi, Claudio
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- A facile one-pot synthesis of substituted N-{[2-(aminocarbonyl)phenylamino]thioxomethyl}benzamides and 2-aryl-quinazolin-4(3H)-ones
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The substituted N-{[2-(aminocarbonyl)phenylamino]thioxomethyl}benzamides and 2-arylquinazolin-4(3H)-ones are synthesized by the reaction of ammonium thiocyanate and aroyl chlorides with 2-amino-benzamide under solvent-free conditions or under reflux in MeCN.
- Mohebat,Raja,Mohammadian, Gh.
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- Polystyrene-Supported Palladium (Pd?PS)-Catalyzed Carbonylative Annulation of Aryl Iodides Using Oxalic Acid as a Sustainable CO Source for the Synthesis of 2-Aryl Quinazolinones
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An efficient and convenient strategy for the synthesis of diversely substituted quinazolinones from o-carbamoyl/cyano aniline and aryl iodides using oxalic acid as a CO source under polystyrene supported palladium (Pd?PS) nanoparticles (NPs) catalyzed con
- Ram, Shankar,Shaifali,Chauhan, Arvind Singh,Sheetal,Sharma, Ajay Kumar,Das, Pralay
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- Structure-based drug design: Synthesis and biological evaluation of quinazolin-4-amine derivatives as selective Aurora A kinase inhibitors
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Aurora kinases play critical roles in the regulation of the cell cycle and mitotic spindle assembly. Aurora A kinase, a member of the Aurora protein family, is frequently highly expressed in tumors, and selective Aurora A inhibition serves as a significant component of anticancer therapy. However, designing highly selective Aurora A inhibitors is difficult because Aurora A and B share high homology and differ only by three residues in their ATP-binding pockets. Through structure-based drug design, we designed and synthesized a series of novel quinazolin-4-amine derivatives. These derivatives act as selective Aurora A kinase inhibitors by exploiting the structural differences between Aurora A and B. The selectivities of most compounds were improved (the best up to >757-fold) when comparing with the lead compound (3-fold). In vitro biochemical and cellular assays revealed that compound 6 potently inhibited Aurora A kinase and most human tumor cells. Furthermore, compound 6 effectively suppressed carcinoma, such as triple-negative breast cancers (TNBC) in an animal model. Therefore, compound 6 might serve as a promising anticancer drug. Moreover, through molecular dynamic (MD) analysis, we have identified that a salt bridge formed in Aurora B is key contributor for the isoform selectivity of the inhibitor. This salt bridge has not been previously detected in the reported crystal structure of Aurora B. These results might provide a crucial basis for the further development of highly potent inhibitors with high selectivity for Aurora A.
- Long, Liang,Wang, Yong-Heng,Zhuo, Jun-Xiao,Tu, Zheng-Chao,Wu, Ruibo,Yan, Min,Liu, Quentin,Lu, Gui
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- Quinazolinones from o-Aminobenzonitriles by One-Pot Sequential Selective Hydration/Condensation/Acceptorless Dehydrogenation Catalyzed by an Iridium Complex
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A new strategy for the direct synthesis of quinazolinones from o-aminobenzonitriles was proposed and accomplished. In the presence of [Cp?IrCl2]2 (Cp?=pentamethylcyclopentadienyl), a variety of desirable products was obtained easily through the one-pot sequential selective hydration/condensation/acceptorless dehydrogenation. This protocol is highly attractive because it uses readily available starting materials, has a high atom efficiency, good to excellent yields, and minimal consumption of chemicals and energy. Notably, this research exhibited new potential for the development of transition-metal-catalyzed one-pot sequential reactions that involve acceptorless dehydrogenation.
- Zhao, Wei,Liu, Pengcheng,Li, Feng
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- Iodine: Selectively promote the synthesis of mono substituted quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones in one-pot
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(Chemical Equation Presented) A general and versatile one-pot three-component procedure for the selective synthesis of mono substituted quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones were described. The selectivity could be controlled by the ratio of iodine concentration.
- Zeng, Li-Yan,Cai, Chun
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- One-pot synthesis of quinazolinones via iridium-catalyzed hydrogen transfers
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A one-pot oxidative cyclization of primary alcohols with o-aminobenzamides to quinazolinones was successfully achieved using [Cp*IrCl 2]2 (Cp* = pentamethylcyclopentadienyl) as a catalyst under hydrogen transfer conditions.
- Zhou, Jianguang,Fang, Jie
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- Lewis acid-catalyzed 2-arylquinazoline formation from: N ′-arylbenzimidamides and paraformaldehyde
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An efficient procedure for the synthesis of 2-arylquinazolines from N′-arylbenzimidamides has been developed under transition-metal-free conditions. In this process, stable and low-toxicity paraformaldehyde was used as the carbon source. A broad range of
- Cheng, Xiufang,Wang, Huamin,Xiao, Fuhong,Deng, Guo-Jun
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- A magnetically retrievable copper ionic liquid nanocatalyst for cyclooxidative synthesis of 2-phenylquinazolin-4(3: H)-ones
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In the present work, we report the design and fabrication of a copper-containing ionic liquid supported magnetic nanocatalyst via a convenient and straightforward synthetic approach for the formation of 2-phenylquinazolin-4(3H)-ones using o-aminobenzamide and benzaldehydes as the reaction partners. The successful formation and properties of the as-prepared catalyst have been thoroughly investigated using diverse physico-chemical techniques including FT-IR, XRD, FE-SEM, TEM, ICP, VSM, BET and TGA. Using this nanocatalytic system, a variety of 2-phenylquinazolin-4(3H)-ones are synthesized in excellent yields with operational ease and short reaction times in an environmentally preferable solvent under open air and without using any external oxidizing agent. Besides, the catalyst possessed facile magnetic recoverability and remarkable reusability for six consecutive runs without any appreciable decrease in the catalytic efficiency.
- Gupta, Radhika,Arora, Gunjan,Yadav, Priya,Dixit, Ranjana,Srivastava, Anju,Sharma, Rakesh Kumar
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- Design, synthesis and in Vitro antiproliferative activity of novel isatin-quinazoline hybrids
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Using a molecular hybridization approach, a new series of isatin-quinazoline hybrids 15a-o was designed and synthesized via two different synthetic routes. The target compounds 15a-o were prepared by the reaction of quinazoline hydrazines 12a-e with indoline-2,3-diones 13a-c or by treating 4-chloroquinazoline derivatives 11a-e with isatin hydrazones 14a-c. The in vitro anticancer activity of the newly synthesized hybrids was evaluated against the liver HepG2, breast MCF-7 and colon HT-29 cancer cell lines. A distinctive selective growth inhibitory effect was observed towards the HepG2 cancer cell line. Compounds 15b, 15g and 15l displayed the highest potency, with IC50 values ranging from 1.0 ± 0.2 to 2.4 ± 0.4 mM, and they were able to induce apoptosis in HepG2 cells, as evidenced by enhanced expression of the pro-apoptotic protein Bax and reduced expression of the anti-apoptotic protein Bcl-2, in addition to increased caspase-3 levels.
- Fares, Mohamed,Eldehna, Wagdy M.,Abou-Seri, Sahar M.,Abdel-Aziz, Hatem A.,Aly, Mohamed H.,Tolba, Mai F.
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- Copper (II)-supported polyethylenimine-functionalized magnetic graphene oxide as a catalyst for the green synthesis of 2-arylquinazolin-4(3H)-ones
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A novel copper (II) catalyst supported on polyethylenimine-functionalized magnetic graphene oxide (denoted Cu@PEI-MGO) has been developed and applied for the cyclization of benzylacetamide with 2-aminobenzamide to afford 2-arylquinazolin-4(3H)-ones in acetonitrile as an inexpensive, non-toxic and reusable solvent medium. Cu@PEI-MGO was characterized by transmission electron microscopy, scanning electron microscopy, thermo-gravimetric analysis, and Fourier-transform infra-red spectroscopy.
- Sayahi, Mohammad Hosein,Bahadorikhalili, Saeed,Saghanezhad, Seyyed Jafar,Mahdavi, Mohammad
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- Metal- and Oxidant-Free Synthesis of Quinazolinones from β-Ketoesters with o-Aminobenzamides via Phosphorous Acid-Catalyzed Cyclocondensation and Selective C-C Bond Cleavage
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A general and efficient phosphorous acid-catalyzed cyclocondensation of β-ketoesters with o-aminobenzamides via selective C-C bond cleavage leading to quinazolinones is developed. This reaction proceeds smoothly under metal- and oxidant-free conditions, giving both 2-alkyl- and 2-aryl-substituted quinazolinones in excellent yields. This strategy can also be applied to the synthesis of other N-heterocycles, such as benzimidazoles and benzothiazoles.
- Li, Zhongwen,Dong, Jianyu,Chen, Xiuling,Li, Qiang,Zhou, Yongbo,Yin, Shuang-Feng
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- Bronsted acidic ionic liquids: New, efficient, and green promoter system for the synthesis of 4(3H)-quinazolinones
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A simple, inexpensive, and efficient new synthesis of 4(3H)-quinazolinones from the reaction of 2-aminobenzamide with aroyl chlorides in the presence of two new halogen-free Brnsted acidic ionic liquids, 3-methyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate [(CH2)4SO 3HMIM][HSO4] and 1-(4-sulfonic acid) butylpyridinium hydrogen sulfate [(CH2)4SO3HPY][HSO4], green and reusable catalysts, with excellent product yields under solvent-free conditions is reported. The products could be separated simply from the catalyst, and the catalyst could be recycled without noticeably decreasing the catalytic activity.
- Heravi, Majid M.,Tavakoli-Hoseini, Niloofar,Bamoharram, Fatemeh F.
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- Synthesis and biological evaluation of novel benzimidazole derivatives and analogs targeting the NLRP3 inflammasome
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A series of benzo[d]imidazole analogues of thiabenzole were synthesized and their anti-inflammatory activities toward NLRP3 (nucleotide-binding domain leucine-rich repeat containing protein family, pyrin domain-containing 3, also known as cryopyrin or NALP3) inflammasome were evaluated in vitro. Two lead compounds, TBZ-09 and TBZ-21, were identified by anti-production of IL-1β. In the second round of biological evaluation, based on the lead, 34 more compounds were synthesized and their in vitro anti-inflammatory activities were investigated. Several compounds were identified as anti-inflammatory agents that can reduce IL-1β expression in a dose-dependent manner. A preliminary structure-activity relationship is also summarized here.
- Pan, Liangkun,Hang, Nan,Zhang, Chao,Chen, Yu,Li, Shuchun,Sun, Yang,Li, Zhongjun,Meng, Xiangbao
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- Highly efficient solvent-free synthesis of quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones using tetrabutylammonium bromide as novel ionic liquid catalyst
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A simple and efficient procedure for the synthesis of 2-arylquinazolin-4(3H)-ones has been developed through cyclocondensation of 2-aminobenzamide with aromatic aldehydes using tetrabutylammonium bromide (TBAB) as novel neutral ionic liquid catalyst in the presence of copper (II) chloride (CuCl2) as oxidizing agent under solvent-free conditions at 100 °C. In the absence of CuCl2 and under a nitrogen atmosphere, the unoxidized intermediates, 2-aryl-2,3-dihydroquinazolin-4(1H)-ones, were isolated. Treatment of these intermediates with CuCl2 in TBAB media gave the oxidized products 2-arylquinazolin-4(3H)-ones. On the other hand, cyclocondensation of 2-aminobenzamide with aromatic aldehydes in TBAB under microwave irradiation directly gave 2-arylquinazolin-4(3H)-ones.
- Davoodnia,Allameh,Fakhari,Tavakoli-Hoseini
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- Potassium hydroxide-promoted transition-metal-free synthesis of 4(3H)-quinazolinones
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We have developed a KOH-promoted transition-metal-free synthesis of 2-substituted 4(3H)-quinazolinones from anthranilamides and benzyl alcohols or cinnamyl alcohol with air as oxidant. The protocol is simple, practical, and cost saving. Graphical abstract: [Figure not available: see fulltext.]
- Qiu, Dezhi,Wang, Yanyan,Lu, Dongming,Zhou, Lihong,Zeng, Qingle
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- A practical synthesis of quinazolinones via intermolecular cyclization between 2-halobenzamides and benzylamines catalyzed by copper(I) immobilized on MCM-41
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The heterogeneous tandem N-arylation/oxidative C–H amidation of 2-halobenzamides and benzylamines was achieved in DMSO at 110 or 120 °C by using an MCM-41-immobilized L-proline copper(I) complex [MCM-41-L-Proline-CuBr] as the catalyst and air as the oxidant, yielding a variety of quinazolinone derivatives in good yields. The new MCM-41-L-Proline-CuBr catalyst can easily be prepared from commercially readily available and inexpensive reagents and recovered by filtration of the reaction mixture, and reused up to seven times with almost consistent activity.
- Yan, Nan,You, Chongren,Cai, Mingzhong
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- A novel magnetically separable laccase-mediator catalyst system for the aerobic oxidation of alcohols and 2-substituted-2,3-dihydroquinazolin-4(1H)-ones under mild conditions
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In this study, a magnetically reusable artificial metalloenzyme has been constructed by co-immobilization of palladium nanoparticles as a strong oxidizing catalyst and laccase as an oxygen-activating enzyme into the cavities of magnetic mesocellular foams
- Shokri, Zahra,Azimi, Nahid,Moradi, Sirvan,Rostami, Amin
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- Photocatalyst-free visible-light-promoted quinazolinone synthesis at room temperature utilizing aldehydes generatedin situ viaC=C bond cleavage
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This is the first report on a facile tandem route for synthesizing quinazolinones at room temperature from various aminobenzamides andin situ-generated aldehydes. The latter was formedviaC=C bond cleavage, and the overall reaction proceeded using molecular oxygen as a clean oxidant in the absence of a photocatalyst. Visible light, which was indispensable for the entire course of the reaction, played multiple roles. It initially cleaved styrene to an aldehyde, then facilitated its cyclization with ano-substituted aniline, and finally promoted the dehydrogenation of the cyclized intermediate. The previous step provided the feedstock for the next step in the reaction, thereby preventing volatilization, oxidation, and polymerization of the aldehyde. Thus, the overall process is simple, environmentally benign, and economically feasible.
- Xie, Zongbo,Lan, Jin,Yan, Liyuan,Chen, Xuehua,Li, Qian,Meng, Jia,Le, Zhanggao
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- Y(OTf)3-catalyzed heterocyclic formation via aerobic oxygenation: An approach to dihydro quinazolinones and quinazolinones
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The Y(OTf)3-catalyzed aerobic oxidative cyclization reaction for the selective synthesis of dihydroquinazolinones and quinazolinones has been developed. This method provides a practical, effective and green synthetic approach to dihydroquinazolinones and quinazolinones which both are important units in many biologically active compounds.
- Shang, Ying-Hui,Fan, Li-Yan,Li, Xiang-Xiong,Liu, Meng-Xia
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- A facile vanadium-catalyzed aerobic oxidative synthesis of quinazolinones from 2-aminobenzamides with aldehydes or alcohols
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An efficient and simple VO(acac)2-catalyzed approach to the synthesis of quinazolinones has been developed. Various substituted quinazolinones have been synthesized from 2-aminobenzamides with alcohols or aldehydes in good to excellent yields with molecular oxygen as the oxidant. The process can also be scaled up.
- Bie, Zhixing,Li, Guosong,Wang, Lianyue,Lv, Ying,Niu, Jingyang,Gao, Shuang
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- Br?nsted acid catalyzed synthesis of 2‐aryl‐quinazolinones via cyclization of 2‐aminobenzamide with benzonitriles in PEG
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A simple and efficient Br?nsted acid catalyzed synthesis of 2‐aryl‐quinazolinones via cyclization of 2‐aminobenzamides with benzonitrile in PEG under metal and ligand‐free condition. All substituted benzonitriles were also well participated with the formation of the corresponding products in moderate to good yields.
- Matcha, Sowbhagya Lakshmi,Karasala, Bharat Kumar,Botsa, Sathish Mohan,Vidavalur, Siddaiah
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- Vanadium-catalyzed synthesis of 4(3H)-quinazolinones from anthranilamides and aryl aldehydes
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An efficient synthesis of 2-substituted and 2,3-disubstituted quinazolin-4(3- H)-ones via tandem reaction of anthranilamides and aromatic aldehydes catalyzed by vanadyl acetylacetonate with 1 mol% loading under an air atmosphere is described. This new method is associated with several advantages such as low catalyst loading (only 1 mol%), use of green oxidant in the form of air, high atom economy, and good to excellent yields. A mechanism of vanadium-catalyzed synthesis of 4(3H)-quinazolinones has also been proposed. Copyright
- Zhan, Dan,Li, Tianbin,Zhang, Xiaoping,Dai, Chuan,Wei, Haidong,Zhang, Yuyu,Zeng, Qingle
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- Br?nsted acid-catalyzed selective C-C bond cleavage of 1,3-diketones: A facile synthesis of 4(3H)-quinazolinones in aqueous ethyl lactate
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A facile and green approach was developed for the synthesis of 4(3H)-quinazolinones by using camphorsulfonic acid as a catalyst in an aqueous solution of biodegradable ethyl lactate. Various 2-aryl-, 2-alkyl-, and 2-(4-oxoalkyl)quinazolinones were obtained by cyclization of 2-aminobenzamides with a wide range of acyclic or cyclic 1,3-diketones via C-C bond cleavage in satisfactory to excellent yields.
- Shen, Guanshuo,Zhou, Haifeng,Du, Peng,Liu, Sensheng,Zou, Kun,Uozumi, Yasuhiro
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- Synthesis, antimicrobial and nematicidal evaluation of a new class of triazolo[4,3-c]quinazolinylthiazolidinones
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In an attempt to find a new class of antimicrobial and nematicidal agents, a series of 2-aryl/heteryl-3-(5-phenyl[1,2,4]triazolo[4,3-c]quinazolin-3-yl)-1,3-thiazolidin-4-ones 5a-k was prepared by one-pot three-component reaction, involving 5-phenyl[1,2,4]triazolo[4,3-c]quinazolin-3-amine 4, aryl/heteroaryl aldehydes and thioglycolic acid, and characterized by physicochemical as well as spectral means. All the newly synthesized compounds 5a-k were tested in vitro for their antimicrobial activity against three representative Gram-positive (Bacillus subtilis, Staphylococcus aureus, Micrococcus luteus), Gram-negative (Proteus vulgaris, Salmonella typhimurium, Escherichia coli) bacteria and four fungal strains (Candida albicans, Aspergillus fumigatus, Trichophyton rubrum, Trichophyton mentagrophytes). These compounds 5a-k, were also evaluated for their nematicidal activity against two nematodes (Ditylenchus myceliophagus, Caenorhabditis elegans). Except phenyl substituted, all the ten aryl/heteroaryl substituted compounds 5b-k showed significant antimicrobial and nematicidal properties against tested microorganisms. Particularly, compounds 5b, 5c, 5g, 5h, 5j and 5k containing electron-withdrawing substituents like chlorophenyl, nitrophenyl, furyl and 1,3-benzodioxole exhibited promising activity comparable to employed standards Ampicillin, Amphotericin B and Levamisole, and emerged as potent antimicrobial and nematicidal agents.
- Sanjeeva Reddy, Cherkupally,Rajesh Kumar, Gaddam,Sunitha, Bommineni
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- Visible light induced tandem reactions: An efficient one pot strategy for constructing quinazolinones using in-situ formed aldehydes under photocatalyst-free and room-temperature conditions
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A facile tandem route has been developed for constructing quinazolinones from various aminobenzamides and in-situ generated aldehydes. Visible light was found to play a dual role: first oxidizes the alcohol to the aldehyde and then facilitates its cyclization with o-substituted aniline. Furthermore, alcohols are perfect alternatives to aldehydes because they are greener, more available, more economical, more stable, and less toxic than aldehydes. The first reaction step continuously provides material for the second step, which effectively reduces loss through volatilization, oxidation, and polymerization of the aldehyde, while avoiding its toxicity. A variety of quinazolinones can be prepared in the presence of visible light without any additional photocatalyst. The developed synthesis protocol proceeds with the merits of mild conditions, broad substrate scope, operational simplicity, and high atom efficiency, with an eco-energy source under metal-free, photocatalyst-free, and ambient conditions.
- Xie, Zongbo,Lan, Jin,Zhu, Haibo,Lei, Gaoyi,Jiang, Guofang,Le, Zhanggao
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- Light induced oxidation of 2,3-dihydroquinazolin-4(1H)-ones
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Light induced oxidation of various of 2-substituted 2,3-dihydroquinazolin- 4(1H)-ones (DHQZs) results smoothly the formation of quinazolin-4(3H)-ones (QZs) product. The electronic nature of the substituent on the 2-position and also the nature of solvent
- Memarian, Hamid R.,Ebrahimi, Saeid
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- One-pot synthesis of polyhydropyrido[1,2-a]indoles and tetracyclic quinazolinones from 2-arylindoles using copper-mediated oxidative tandem reactions
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We developed facile one-pot methods for the transformation of 2-arylindoles to polyhydropyrido[1,2-a]indoles and tetracyclic quinazolinones. The copper-catalyzed oxidation of 2-arylindoles to C-acylimines followed by aza-Diels–Alder reactions or oxidative
- Yamashita, Mitsuaki,Nishizono, Yukari,Himekawa, Seiya,Iida, Akira
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- Simple, selective, and practical synthesis of 2-substituted 4(3H)-quinazolinones by Yb(OTf)3-catalyzed condensation of 2-aminobenzamide with carboxamides
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A simple, selective, and practical synthetic method of 4(3H)-quinazolinones is realized by Yb(OTf)3-catalyzed condensation of 2-aminobenzamide with carboxamides. As the reaction proceeds, NH3 and H2O were formed as byproducts; however, Yb(OTf)3 can operate as an efficient Lewis acid catalyst without deactivation.
- Yoshimura, Tsutomu,Yuanjun, Di,Kimura, Yu,Yamada, Hisatsugu,Toshimitsu, Akio,Kondo, Teruyuki
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- Design, synthesis, characterization, enzymatic inhibition evaluations, and docking study of novel quinazolinone derivatives
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In this study, novel quinazolinone derivatives 7a-n were synthesized and evaluated against metabolic enzymes including α-glycosidase, acetylcholinesterase, butyrylcholinesterase, human carbonic anhydrase I, and II. These compounds exhibited high inhibitory activities in comparison to used standard inhibitors with Ki values in the range of 19.28–135.88 nM for α-glycosidase (Ki value for standard inhibitor = 187.71 nM), 0.68–23.01 nM for acetylcholinesterase (Ki value for standard inhibitor = 53.31 nM), 1.01–29.56 nM for butyrylcholinesterase (Ki value for standard inhibitor = 58.16 nM), 10.25–126.05 nM for human carbonic anhydrase I (Ki value for standard inhibitor = 248.18 nM), and 13.46–178.35 nM for human carbonic anhydrase II (Ki value for standard inhibitor = 323.72). Furthermore, the most potent compounds against each enzyme were selected in order to evaluate interaction modes of these compounds in the active site of the target enzyme. Cytotoxicity assay of the title compounds 7a-n against cancer cell lines MCF-7 and LNCaP demonstrated that these compounds do not show significant cytotoxic effects.
- Pedrood, Keyvan,Sherafati, Maedeh,Mohammadi-Khanaposhtani, Maryam,Asgari, Mohammad Sadegh,Hosseini, Samanesadat,Rastegar, Hossein,Larijani, Bagher,Mahdavi, Mohammad,Taslimi, Parham,Erden, Yavuz,Günay, Sevilay,Gul?in, ?lhami
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- Aerobic photooxidative synthesis of 2-aryl-4-quinazolinones from aromatic aldehydes and aminobenzamide using catalytic amounts of molecular iodine
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This study reports a safe, mild, and environmentally benign synthetic method toward 2-aryl-4-quinazolinones from aromatic aldehydes and aminobenzamides through a cyclization-oxidation sequence using a catalytic amount of iodine, which serves as both a Lewis acid and an oxidant, harmless visible light irradiation, and molecular oxygen as the terminal oxidant.
- Nagasawa,Matsusaki,Nobuta,Tada,Miura,Itoh
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- The mechanochemical synthesis of quinazolin-4(3H)-ones by controlling the reactivity of IBX
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Performing any synthesis using several arylamines and hypervalent iodine(V) reagents by direct mixing is unrealistic because of the high exothermic reaction or explosion. Herein we demonstrate, when anilines were substituted with an amide group at the orthoposition, successful chemical reactions could be performed due to intramolecular control. At maximum contact of the reacting substances, i.e., under solvent-free mechanochemical conditions, 2-aminobenzamides, aryl-, alkylaldehydes and the iodine(V) reagent o-iodoxybenzoic acid (IBX) led to substituted quinazolin-4(3H)-one derivatives in fair yields.
- Alam, Md Toufique,Maiti, Saikat,Mal, Prasenjit
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- C2-substituted quinazolinone derivatives exhibit A1 and/or A2A adenosine receptor affinities in the low micromolar range
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Antagonists of the adenosine receptors (A1 and A2A subtypes) are widely researched as potential drug candidates for their role in Parkinson's disease-related cognitive deficits (A1 subtype), motor dysfunction (A2A subtype) and to exhibit neuroprotective properties (A2A subtype). Previously the benzo-α-pyrone based derivative, 3-phenyl-1H-2-benzopyran-1-one, was found to display both A1 and A2A adenosine receptor affinity in the low micromolar range. Prompted by this, the α-pyrone core was structurally modified to explore related benzoxazinone and quinazolinone homologues previously unknown as adenosine receptor antagonists. Overall, the C2-substituted quinazolinone analogues displayed superior A1 and A2A adenosine receptor affinity over their C2-substituted benzoxazinone homologues. The benzoxazinones were devoid of A2A adenosine receptor binding, with only two compounds displaying A1 adenosine receptor affinity. In turn, the quinazolinones displayed varying degrees of affinity (low micromolar range) towards the A1 and A2A adenosine receptor subtypes. The highest A1 adenosine receptor affinity and selectivity were favoured by methyl para-substitution of phenyl ring B (A1Ki = 2.50 μM). On the other hand, 3,4-dimethoxy substitution of phenyl ring B afforded the best A2A adenosine receptor binding (A2AKi = 2.81 μM) among the quinazolinones investigated. In conclusion, the quinazolinones are ideal lead compounds for further structural optimization to gain improved adenosine receptor affinity, which may find therapeutic relevance in Parkinson's disease-associated cognitive deficits and motor dysfunctions as well as exerting neuroprotective properties.
- Pieterse, Lianie,Terre'Blanche, Gisella,van der Walt, Mietha M.
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- Synthesis, biological evaluation and molecular modelling insights of 2-arylquinazoline benzamide derivatives as anti-tubercular agents
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New 2-arylquinazoline benzamide derivatives were synthesized and screened against H37RV strain, compounds displayed specific and potent anti-mycobacterial activity against Mycobacterium tuberculosis. 9a, 9c, 9d, 9e, 9f, 9h, 13b, 17d and 17e exhibited selective and good inhibitory activity against Mycobacterium tuberculosis with the MIC values range of 4–32 μg/mL. Molecular modelling studies also supports that the active molecules can fit well in the binding pocket of GlmU with good ligand-protein interactions, strong binding energies and satisfactory ADMET properties results (obeys the Lipinski rule of 5). Comprehensively, the studies recommended that these new quinazoline derivatives have the potential to be further develop as prospective anti-mycobacterial leads.
- Ahmad, Md Naiyaz,Akhir, Abdul,Chopra, Sidharth,Gatadi, Srikanth,Gour, Jitendra,Kaul, Grace,Madhavi, Y. V.,Malasala, Satyaveni,Nanduri, Srinivas,Shukla, Manjulika
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- A Cu (NO3)2.3H2O catalysed facile synthesis of substituted 4(3H)-quinazolinones and benzimidazoles
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One pot synthesis of alkyl, aryl, heteroaryl mono(2)substituted 4(3H)-quinazolinones and 2-aryl or heteroaryl, 1-arylmethyl or heteroarylmethyl -1H-benzimidazoles using a water soluble Cu (NO3)2.3H 2O catalyst at room/ambient temperature in excellent yield.
- Durgareddy,Ravikumar,Ravi,Adapa, Srinivas R.
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- Survey Reactivity of Some Substituted Quinazolinones with Pentafluoro(chloro)pyridine
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A new series of 4-hetroaryl substituted quinazolines were designed and synthesized by the reaction of pentafluoro(chloro)pyridine and 2-substituted quinazolinone. The aromatic nucleophilic substitution of pentafluoro(chloro)pyridine with quinazolinone occurs at the 4-position of pyridine ring by the oxygen site (O-centered nucleophile) of quinazolinone. The structures of all the compounds were confirmed by IR, 1H NMR, 19F NMR, and 13C NMR spectroscopy as well as elemental analysis.
- Ranjbar-Karimi, Reza,Davodian, Tayebeh,Mehrabi, Hossein
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- A copper catalyzed multicomponent cascade redox reaction for the synthesis of quinazolinones
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A copper catalyzed multicomponent cascade redox reaction for the synthesis of various quinazolinones starting from easily available 2-bromobenzamides, benzylic alcohols and sodium azide as a nitrogen source has been developed. The reaction involves copper catalyzed azidation of 2-bromobenzamide via an SNAr reaction and oxidation of benzyl alcohol followed by sequential reduction-condensation-oxidation to produce quinazolinones.
- Shinde, Mahesh H.,Kshirsagar, Umesh A.
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- Access to 2-Arylquinazolin-4(3H)-ones through Intramolecular Oxidative C(sp3)?H/N?H Cross-Coupling Mediated by I2/DMSO
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A novel approach for the synthesis of 2-arylquinazolin-4(3H)-ones was developed. A series of title compounds were obtained with good functional group tolerance and good yields by I2/DMSO-mediated intramolecular oxidative cross-coupling of 2-(benzylamino)benzamides to form C=N double bonds. This method was applicable for gram-scale synthesis. A proposed reaction pathway based on some control experiments was also provided.
- Wen, Simiaomiao,Du, Yifan,Liu, Yiwen,Cui, Xiaofeng,Liu, Qixing,Zhou, Haifeng
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- Aromatization as an Impetus to Harness Ketones for Metallaphotoredox-Catalyzed Benzoylation/Benzylation of (Hetero)arenes
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Herein we report ketones as feedstock materials in radical cross-coupling reactions under Ni/photoredox dual catalysis. In this approach, simple condensation first converts ketones into prearomatic intermediates that then act as activated radical sources for cross-coupling with aryl halides. Our strategy enables the direct benzylation/benzoylation of (hetero)arenes under mild reaction conditions with high functional group tolerance.
- Lee, Shao-Chi,Li, Li-Yun,Tsai, Zong-Nan,Lee, Yi-Hsin,Tsao, Yong-Ting,Huang, Pin-Gong,Cheng, Cheng-Ku,Lin, Heng-Bo,Chen, Ting-Wei,Yang, Chung-Hsin,Chiu, Cheng-Chau,Liao, Hsuan-Hung
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- N^N^O hydrazone capped pincer type palladium complex catalysed construction of quinazolinones from alcohols
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New Pincer type Pd(II) complex [Pd(NNO)(PPh3)] (1) prompted synthesis of quinazolinones via dehydrogenative coupling of readily accessible alcohols, and o-aminobenzamide is described. A diverse range of quinazolinones has been synthesized efficiently with good to excellent yields employing low catalyst loading (0.5 mol%) under the aerobic condition without any additives/oxidants. A plausible mechanism for the construction of quinazolinones has been proposed via cyclic aminal intermediate. Large-scale synthesis attests to the productiveness of the current strategy.
- Anandaraj, Pennamuthiriyan,Kamatchi, Thangavel Sathiya,Ramesh, Rengan
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- A bagasse-supported magnetic manganese dioxide nanoparticle: applications in the selective aerobic oxidation of alcohols and one-pot tandem oxidative synthesis of quinazolinones
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Magnetic manganese dioxide nanoparticles (MnO2-Fe3O4) were coated on sugarcane bagasse as a sugar industrial waste and bio-support (MnO2-Fe3O4@bagasse) via an in situ reduction strategy, in which potassium permanganate was used as the precursor of MnO2 and sugarcane bagasse as a bio-support and reducing agent of KMnO4. The synthesized bio-based catalyst was characterized by X-ray diffraction, thermogravimetric analysis, inductively coupled plasma optical emission spectroscopy, scanning electron microscopy, energy dispersive spectroscopy, Brunauer–Emmett–Teller surface area analysis, and vibrating sample magnetometer analysis. The catalyst was successfully utilized in the selective aerobic oxidation of primary and secondary benzylic alcohols to their corresponding carbonyl compounds and one-pot tandem oxidative synthesis of 2-(substituted)quinazoline-4(3H)-ones from the o-aminobenzamide and aromatic alcohols in the absence of oxidizing reagent or initiator. Graphical abstract: [Figure not available: see fulltext.]
- Farhid, Hassan,Hajishaabanha, Fatemeh,Rashidi Vahid, Adina,Shaabani, Ahmad,Shaabani, Shabnam
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- Catalyst-free synthesis of quinazolinones by oxidative cyclization under visible light in the absence of additives
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A general metal-free oxidative cyclization route was developed to synthesize quinazolinones under visible light. A series of substituted 2-aminobenzamides were reacted with aldehydes or ketones to produce the desired quinazolinones in good yields. Most importantly, the reaction did not require excess oxidant or high temperatures.
- Yang, Jiangnan,Xie, Zongbo,Chen, Zhongsheng,Jin, Liang,Li, Qian,Le, Zhanggao
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p. 1496 - 1501
(2021/05/03)
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- Electrochemical synthesis of quinazolinone: via I2-catalyzed tandem oxidation in aqueous solution
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The development of protocols for synthesizing quinazolinones using biocompatible catalysts in aqueous medium will help to resolve the difficulties of using green and sustainable chemistry for their synthesis. Herein, using I2 in coordination with electrochemical synthesis induced a C-H oxidation reaction which is reported when using water as the environmentally friendly solvent to access a broad range of quinazolinones at room temperature. The reaction mechanism strongly showed that I2 cooperates electrochemically promoted the oxidation of alcohols, then effectively cyclizing amides to various quinazolinones.
- Hou, Huiqing,Ma, Xinhua,Lin, Yingying,Lin, Jin,Sun, Weiming,Wang, Lei,Xu, Xiuzhi,Ke, Fang
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p. 17721 - 17726
(2021/05/29)
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- Visible-light-mediated organoboron-catalysed metal-free dehydrogenation of N-heterocycles using molecular oxygen
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The surge of photocatalytic transformation not only provides unprecedented synthetic methods, but also triggers the enthusiasm for more sustainable photocatalysts. On the other hand, oxygen is an ideal oxidant in terms of atom economy and environmental friendliness. However, the poor reactivity of oxygen at the ground state makes its utilization challenging. Herein, a visible-light-induced oxidative dehydrogenative process is disclosed, which uses an organoboron compound as the photocatalyst and molecular oxygen as the sole oxidant.Viathis approach, an array of N-heterocycles have been accessed under metal-free mild conditions, in good to excellent yields.
- Wei, Lanfeng,Wei, Yu,Xu, Liang,Zhang, Jinli
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supporting information
p. 4446 - 4450
(2021/06/30)
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- Method for preparing N - heterocyclic ring through visible light mediated dehydrogenation
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The invention discloses a method for preparing N - heterocyclic rings through visible light mediated dehydrogenation, and the reaction can be carried out under the conditions of room temperature and visible light without heating. The novel tetra-coordination N-N - diaryl chelating borate compound serves as a photocatalyst, so that the use of a noble metal photocatalyst is avoided, precious metal residue in the reaction product can be reduced as much as possible, and the method is more suitable for synthesizing bioactive molecules.
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Paragraph 0092-0097
(2021/10/02)
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- Palladium(II) N^O Chelating Complexes Catalyzed One-Pot Approach for Synthesis of Quinazolin-4(3 H)-ones via Acceptorless Dehydrogenative Coupling of Benzyl Alcohols and 2-Aminobenzamide
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A convenient protocol for the one-pot synthesis of quinazolin-4(3H)-ones using palladium(II) complexes via dehydrogenative coupling of readily available benzyl alcohols and 2-aminobenzamide has been described. New structurally related Pd(II) N^O chelating complexes of general configuration [Pd(L)Cl(PPh3)] (where L = dimethylamino benzoylhydrazone ligands) have been designed and synthesized. The formation of the complexes has been recognized by analytical and spectral methods (FT-IR, NMR, HR-MS). The presence of a square-planar geometry around the palladium(II) ion was confirmed by single crystal X-ray diffraction study. A wide range of substituted quinazolinones have been successfully achieved from a diverse range of benzyl alcohols in good to excellent yields using 1.0 mol % of catalyst loading under aerobic conditions. Furthermore, control experiments reveal that the dehydrogenative coupling reaction involves initially the formation of an aldehyde intermediate and subsequent formation of a cyclic aminal intermediate.
- Balaji, Sundarraman,Balamurugan, Gunasekaran,Ramesh, Rengan,Semeril, David
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p. 725 - 734
(2021/04/06)
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- Metal-free catalyst for the visible-light-induced photocatalytic synthesis of quinazolinones
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In the present work, we have developed a novel and environmentally friendly method for the synthesis of quinazolinones using fluorescein as a photocatalyst via a condensation reaction of o-aminobenzamides and aldehydes under visible light irradiation. In this protocol, neither toxic oxidants nor transition-metal catalysts were needed, and a series of quinazolinones could be obtained in high efficiencies. In addition, this reaction can be extended to gram levels and has a large potential of wide application in future industrialization.
- Wang, Rongzhou,Liu, Shiyuan,Li, Longfei,Song, Ao,Yu, Shengsheng,Zhuo, Shuping,Xing, Ling-Bao
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- Visible light mediated selective oxidation of alcohols and oxidative dehydrogenation of N-heterocycles using scalable and reusable La-doped NiWO4nanoparticles
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Visible light-mediated selective and efficient oxidation of various primary/secondary benzyl alcohols to aldehydes/ketones and oxidative dehydrogenation (ODH) of partially saturated heterocycles using a scalable and reusable heterogeneous photoredox catalyst in aqueous medium are described. A systematic study led to a selective synthesis of aldehydes under an argon atmosphere while the ODH of partially saturated heterocycles under an oxygen atmosphere resulted in very good to excellent yields. The methodology is atom economical and exhibits excellent tolerance towards various functional groups, and broad substrate scope. Furthermore, a one-pot procedure was developed for the sequential oxidation of benzyl alcohols and heteroaryl carbinols followed by the Pictet-Spengler cyclization and then aromatization to obtain the β-carbolines in high isolated yields. This methodology was found to be suitable for scale up and reusability. To the best of our knowledge, this is the first report on the oxidation of structurally diverse aryl carbinols and ODH of partially saturated N-heterocycles using a recyclable and heterogeneous photoredox catalyst under environmentally friendly conditions.
- Abinaya, R.,Balasubramaniam, K. K.,Baskar, B.,Divya, P.,Mani Rahulan, K.,Rahman, Abdul,Sridhar, R.,Srinath, S.
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p. 5990 - 6007
(2021/08/24)
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- Synthesis and evaluation of antioxidant properties of 2-substituted quinazolin-4(3H)-ones
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Quinazolinones represent an important scaffold in medicinal chemistry with diverse biological activities. Here, two series of 2-substituted quinazolin-4(3H)-ones were synthesized and evaluated for their antioxidant properties using three different methods, namely DPPH, ABTS and TEACCUPRAC, to obtain key information about the structure-antioxidant activity relationships of a diverse set of substituents at position 2 of the main quinazolinone scaffold. Regarding the antioxidant activity, ABTS and TEACCUPRAC assays were more sensitive and gave more reliable results than the DPPH assay. To obtain antioxidant activity of 2-phenylquinazolin-4(3H)-one, the presence of at least one hydroxyl group in addition to the methoxy substituent or the second hydroxyl on the phenyl ring in the ortho or para positions is required. An additional ethylene linker between quinazolinone ring and phenolic substituent, present in the second series (compounds 25a and 25b), leads to increased antioxidant activity. Furthermore, in addition to antioxidant activity, the derivatives with two hydroxyl groups in the ortho position on the phenyl ring exhibited metal-chelating properties. Our study represents a successful use of three different antioxidant activity evaluation methods to define 2-(2, 3-dihydroxyphenyl)quinazolin-4(3H)-one 21e as a potent antioxidant with promising metal-chelating properties.
- Hrast, Martina,Mravljak, Janez,Slavec, Lara,Sova, Matej
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- Synthesis of quinazolin-4(3H)-ones via electrochemical decarboxylative cyclization of α?keto acids with 2-aminobenzamides
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Herein, an environmentally benign electrochemical protocol has been disclosed for the synthesis of quinazolin-4(3H)-one derivatives from readily available α?keto acids and 2-aminobenzamides. This decarboxylative cyclization process proceeds conveniently in the absence of any homogeneous metal catalysts, bases, or external oxidants. This protocol also features CO2 by-products, mild reaction conditions (room temperature and air atmosphere), and a wide variety of substrate scope, including an array of 2,3-disubstituted quinazolinone products.
- Tian, Qing,Wei, Yu,Xu, Liang,Zhang, Jinli
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- KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes
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KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes have been developed. In this protocol, a variety of nitriles as well as aldehydes react with 2-substituted benzamides to corresponding quinazolin-4(3H)-ones products in good to moderate yields, via the cleavage of C-X and C-N bonds and the formation of double C-N bonds simultaneously, in presence of potassium tert-butoxide.
- Nomula, Vishnuvardhan,Rao, Sadu Nageswara
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supporting information
p. 2602 - 2612
(2021/08/03)
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- Electro-oxidative cyclization: Access to quinazolinones: Via K2S2O8without transition metal catalyst and base
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A K2S2O8-promoted oxidative tandem cyclization of primary alcohols with 2-aminobenzamides to synthesize quinazolinones was successfully achieved under undivided electrolytic conditions without a transition metal and base. The key feature of this protocol is the utilization of K2S2O8 as an inexpensive and easy-to-handle radical surrogate that can effectively promote the reaction via a simple procedure, leading to the formation of nitrogen heterocycles via direct oxidative cyclization at room temperature in a one-pot procedure under constant current. Owing to the use of continuous-flow electrochemical setups, this green, mild and practical electrosynthesis features high efficiency and excellent functional group tolerance and is easy to scale up.
- Hou, Huiqing,Hu, Yongzhi,Ke, Fang,Sun, Weiming,Wu, Xianghua,Yu, Ling,Zhou, Sunying
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p. 31650 - 31655
(2021/11/30)
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- Improved, gram-scale synthesis of sildenafil in water using arylacetic acid as the acyl source in the pyrazolo[4,3-d]pyrimidin-7-one ring formation
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An improved, gram-scale synthesis of the blockbuster drug sildenafil, used for the treatment of male erectile dysfunction, has been developed. Unlike the previous literature, the current method demonstrates the use of arylacetic acid as an acyl source, a cheap oxidant K2S2O8, and water as the reaction medium in the key step of pyrrazolo[4,3-d]pyrimidin-7-one ring formation. As well as being a green and benign approach, the current method reduces the cost by half compared to our previous strategy. In addition, the general relevance of the method has been demonstrated in the synthesis of a variety of quinazolinone and benzothiazole derivatives with excellent functional group tolerance.
- Laha, Joydev K.,Gulati, Upma,Saima,Gupta, Anjali,Indurthi, Harish Kumar
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supporting information
p. 2643 - 2648
(2021/02/16)
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- Synthesis and evaluation of new quinazoline-benzimidazole hybrids as potent anti-microbial agents against multidrug resistant Staphylococcus aureus and Mycobacterium tuberculosis
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Owing to the rapid rise in antibiotic resistance, infectious diseases have become serious threat to public health. There is an urgent need to develop new antimicrobial agents with diverse chemical structures and novel mechanisms of action to overcome the resistance. In recent years, Quinazoline-benzimidazole hybrids have emerged as a new class of antimicrobial agents active against S. aureus and M. tuberculosis. In the current study, we designed and synthesized fifteen new Quinazoline-benzimidazole hybrids and evaluated them for their antimicrobial activity against S. aureus ATCC 29213 and M. tuberculosis H37Rv. These studies led to the identification of nine potent antibacterial agents 8a, 8b, 8c, 8d, 8f, 8g, 8h, 8i and 10c with MICs in the range of 4–64 μg/mL. Further, these selected compounds were found to possess potent antibacterial potential against a panel of drug-resistant clinical isolates which include methicillin and vancomycin-resistant S. aureus. The selected compounds were found to be less toxic to Vero cells (CC50 = 40-≥200 μg/mL) and demonstrated a favourable selectivity index. Based on the encouraging results obtained these new benzimidazol-2-yl quinazoline derivatives have emerged as promising antimicrobial agents for the treatment of MDR- S. aureus and Mycobacterial infections.
- Malasala, Satyaveni,Ahmad, Md Naiyaz,Akunuri, Ravikumar,Shukla, Manjulika,Kaul, Grace,Dasgupta, Arunava,Madhavi,Chopra, Sidharth,Nanduri, Srinivas
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- Linear-Organic-Polymer-Supported Iridium Complex as a Recyclable Auto-Tandem Catalyst for the Synthesis of Quinazolinones via Selective Hydration/Acceptorless Dehydrogenative Coupling from o-Aminobenzonitriles
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A linear-organic-polymer-supported iridium complex Cp*Ir@P4VP, which is designed and synthesized by the coordinative immobilization of [Cp*IrCl2]2 on poly(4-vinylpyridine), was proven to be an efficient heterogeneous autotandem catalyst for synthesizing quinazolinones via selective hydration/acceptorless dehydrogenative coupling from o-aminobenzonitriles. Furthermore, the synthesized catalyst was recycled five times without an obvious decrease in the catalytic activity.
- Hao, Shushu,Yang, Jiazhi,Liu, Peng,Xu, Jing,Yang, Chenchen,Li, Feng
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p. 2553 - 2558
(2021/04/13)
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- Synthesis of Difluoromethyl-Substituted Quinazolines through Selective Difluoromethylation
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A highly selective difluoromethylation of quinazolines has been achieved by using commercially available ethyl bromodifluoroacetate as difluorocarbene precursor, providing the corresponding difluoromethyl substituted quinazoline derivatives with up to 83% yield.
- Peng, Jing,Hu, Ludan,Chen, Mu-Wang,Deng, Zhihong,Peng, Yiyuan
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p. 2286 - 2292
(2021/03/04)
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- Method for photocatalytic synthesis of quinazolinone
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The invention discloses a method for photocatalytic synthesis of quinazolinone. Anthranilamide and aldehyde are used as raw materials, fluorescein is used as a photocatalyst, p-toluene sulfonic acid is used as an auxiliary catalyst, and the quinazolinone is obtained through photocatalytic reaction under the irradiation of visible light. The non-metal catalyst is used, so that the reaction cost is reduced; the reaction conditions are mild, and the reaction can be completed at room temperature; and the method is simple to operate, short in reaction time, simple in post-treatment, high in product yield and more environment-friendly. The method not only has high academic value, but also has a certain industrialization prospect.
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Paragraph 0019-0027; 0047
(2021/07/31)
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- Three-Component Couplings among Heteroarenes, Difluorocyclopropenes, and Water via C-H Activation
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Three-component couplings have been realized for efficiently constructing various nitrogen-containing skeletons via C-H activation, where difluorocyclopropenes have been first identified as coupling partners. Many substrates including sp2 and sp3 C-H substrates were well tolerated, furnishing the corresponding products in good yields. Furthermore, a catalyst-dependent reaction was also developed, enabling divergent construction of two different frameworks. The application value of these reactions was demonstrated in gram-scale experiments with as little as 1 mol % catalyst.
- Liu, Xuexin,Chen, Jian,Yang, Chunyan,Wu, Zhouping,Li, Zhiyang,Shi, Yuesen,Huang, Tianle,Yang, Zhongzhen,Wu, Yong
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supporting information
p. 6831 - 6835
(2021/09/08)
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- Antioxidant and ros inhibitory activities of heterocyclic 2-aryl-4(3h)-quinazolinone derivatives
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Background: Antioxidants are small molecules that prevent or delay the process of oxidations caused by highly reactive free radicals. These molecules are known for their ability to protect various cellular architecture and other biomolecules from oxidative stress and free radicals. Thus, antioxidants play a key role in the prevention of oxidative damages caused by highly reactive free radicals. Methods: In the present study, a series of previously synthesized heterocyclic 2-aryl-4(3H)-quinazolinone derivatives 1-25 were screened for antioxidant activity by employing in vitro DPPH and superoxide anion radical scavenging activities. ROS inhibitory activities were also evaluated by serum-opsonized zymosan activated whole blood phagocytes and isolated neutrophils. Cytotoxicity studies were carried out by employing an MTT assay against the 3T3 cell line. Results: Most of the 2-aryl-4(3H)-quinazolinone derivatives showed potent antioxidant activities in superoxide anion radical scavenging assay with IC50 value ranging between 0.57 μM-48.93 μM, as compared to positive control quercetin dihydrate (IC50 = 94.1 ± 1.1 μM ). Compounds 5, 6, and 14 showed excellent activity in DPPH assay. Compounds 5-8, 12-15, 17, and 20 showed promising activities in the ROS inhibition assay. All compounds were found to be non-cytotoxic against the 3T3 cell line. Structure antioxidant activity has been established. Conclusion: It can be concluded that most of the heterocyclic 2-aryl-4(3H)-quinazolinone derivatives 1-25 are identified as promising antioxidant agents that are capable of fighting against free radicals and oxidative stress. Thus, they can serve as a lead towards treating oxidative stress and related pathologies.
- Choudhary, Muhammad Iqbal,Khan, Khalid Mohammed,Perveen, Shahida,Saad, Syed Muhammad
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p. 806 - 815
(2021/11/17)
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- Iron catalyzed metal-ligand cooperative approaches towards sustainable synthesis of quinolines and quinazolin-4(3H)-ones
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Herein we report simple, efficient, and economically affordable metal-ligand cooperative strategies for synthesizing quinolines and quinazolin-4(3H)-ones via dehydrogenative functionalization of alcohols. Various polysubstituted quinolines and quinazolin-4(3H)-ones were prepared in good yields via dehydrogenative coupling of readily available alcohols with ketones and 2-aminobenzamides, respectively under air using a well-defined Fe(II)-catalyst, ([FeL1Cl2] (1)) bearing a redox-active azo-aromatic pincer 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline) (L1). Control experiments and mechanistic investigation disclose that the one-electron reduced mono-anionic species [1]? bearing an iron-stabilized azo-anion radical ligand catalyzes these reactions. Both iron and the redox-active arylazo ligand participate synergistically during the different steps of these catalytic reactions.
- Mondal, Rakesh,Chakraborty, Gargi,Guin, Amit Kumar,Pal, Subhasree,Paul, Nanda D.
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- Zinc Stabilized Azo-anion Radical in Dehydrogenative Synthesis of N-Heterocycles. An Exclusively Ligand Centered Redox Controlled Approach
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Herein we report an exclusively ligand-centered redox controlled approach for the dehydrogenation of a variety of N-heterocycles using a Zn(II)-stabilized azo-anion radical complex as the catalyst. A simple, easy-to-prepare, and bench-stable Zn(II)-complex (1b) featuring the tridentate arylazo pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline, in the presence of zinc-dust, undergoes reduction to form the azo-anion radical species [1b]- which efficiently dehydrogenates various saturated N-heterocycles such as 1,2,3,4-tetrahydro-2-methylquinoline, 1,2,3,4-tetrahydro-isoquinoline, indoline, 2-phenyl-2,3-dihydro-1H-benzoimidazole, 2,3-dihydro-2-phenylquinazolin-4(1H)-one, and 1,2,3,4-tetrahydro-2-phenylquinazolines, among others, under air. The catalyst has further been found to be compatible with the cascade synthesis of these N-heterocycles via dehydrogenative coupling of alcohols with other suitable coupling partners under air. Mechanistic investigation reveals that the dehydrogenation reactions proceed via a one-electron hydrogen atom transfer (HAT) pathway where the zinc-stabilized azo-anion radical ligand abstracts the hydrogen atom from the organic substrate(s), and the whole catalytic cycle proceeds via the exclusive involvement of the ligand-centered redox events where the zinc acts only as the template.
- Das, Siuli,Mondal, Rakesh,Chakraborty, Gargi,Guin, Amit Kumar,Das, Abhishek,Paul, Nanda D.
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p. 7498 - 7512
(2021/06/30)
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- Electrochemically induced synthesis of quinazolinonesviacathode hydration ofo-aminobenzonitriles in aqueous solutions
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An efficient and practical electrochemically catalyzed transition metal-free process for the synthesis of substituted quinazolinones from simple and readily availableo-aminobenzonitriles and aldehydes in water has been accomplished. I2/base and water play an unprecedented and vital role in the reaction. By electrochemically catalysed hydrolysis ofo-aminobenzonitriles, the synthesis of quinazolinones with benzaldehyde was first proposed. The synthetic utility of this method was demonstrated by gram-scale operation, as well as the preparation of bioactiveN-(2,5-dichlorophenyl)-6-(2,2,2-trifluoroethoxy) pteridin-4-amine, which enables straightforward, practical and environmentally benign quinazolinone formation.
- Yang, Li,Hou, Huiqing,Li, Lan,Wang, Jin,Zhou, Sunying,Wu, Mei,Ke, Fang
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supporting information
p. 998 - 1003
(2021/02/16)
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- Aerobic primary and secondary amine oxidation cascade by a copper amine oxidase inspired catalyst
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Herein, we report a bioinspired catalytic system for the one-pot cascade oxidation of a native primary amine and anin situgenerated non-native secondary amine. The catalyst consists of ano-quinone cofactor phd (1,10-phenanthroline-5,6-dione) and a copper ion and operates under ambient air conditions. Quinazolin-4(3H)-ones, which are common pharmacophores present in numerous pharmaceuticals and bioactive compounds, were synthesized in high yields. A detailed kinetic and mechanistic study elucidates the role of the catalyst in the multi-step oxidative cascade reaction.
- Thorve, Pradip Ramdas,Maji, Biplab
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p. 1116 - 1124
(2021/02/26)
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- An efficient transition-metal-free route to quinazolin-4(3H)-onesvia2-aminobenzamides and thiols
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An efficient approach to quinazolin-4(3H)-ones was developed by a one-pot intermolecular annulation reaction ofo-amino benzamides and thiols. This method has the features of good functional group tolerance, being transition metal and external oxidant free, and easy operation. Varieties of 2-aryl (heteroaryl) quinazolin-4(3H)-one, 2-phenyl-pyrido[2,3-d]pyrimidin-4(3H)-one and 3-phenyl-2H-1,2,4-benzo thiadiazine-1,1-dioxide derivatives were obtained with a yield of up to 98%. The control experiment revealed that the thiol substrate could promote the dehydroaromatization step.
- Dong, Yibo,Wu, Yangjie,Yan, Congcong,Yang, Jinchen,Zhang, Jinli
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p. 15344 - 15349
(2021/09/07)
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- Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines
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A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.
- Neerathilingam, Nalladhambi,Bhargava Reddy, Mandapati,Anandhan, Ramasamy
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p. 15117 - 15127
(2021/10/25)
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- Highly Ordered Mesoporous Cobalt Oxide as Heterogeneous Catalyst for Aerobic Oxidative Aromatization of N-Heterocycles
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N-heterocycles are key structures for many pharmaceutical intermediates. The synthesis of such units normally is conducted under homogeneous catalytic conditions. Among all methods, aerobic oxidative aromatization is one of the most effective. However, in homogeneous conditions, catalysts are difficult to be recycled. Herein, we report a heterogeneous catalytic strategy with a mesoporous cobalt oxide as catalyst. The developed protocol shows a broad applicability for the synthesis of N-heterocycles (32 examples, up to 99 % yield), and the catalyst presents high turnover numbers (7.41) in the absence of any additives. Such a heterogenous approach can be easily scaled up. Furthermore, the catalyst can be recycled by simply filtration and be reused for at least six times without obvious deactivation. Comparative studies reveal that the high surface area of mesoporous cobalt oxide plays an important role on the catalytic reactivity. The outstanding recycling capacity makes the catalyst industrially practical and sustainable for the synthesis of diverse N-heterocycles.
- Cao, Yue,Wu, Yong,Zhang, Yuanteng,Zhou, Jing,Xiao, Wei,Gu, Dong
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p. 3679 - 3686
(2021/06/18)
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- α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water
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A general and efficient method for the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil. More importantly, these reactions can be conducted on a mass scale, and the products can be easily purified through filtration and washing with ethanol (or crystallized).
- Huang, Jian,Chen, Wei,Liang, Jiazhi,Yang, Qin,Fan, Yan,Chen, Mu-Wang,Peng, Yiyuan
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p. 14866 - 14882
(2021/10/25)
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- Possible competitive modes of decarboxylation in the annulation reactions ofortho-substituted anilines and arylglyoxylates
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Annulation reactions ofortho-substituted anilines and arylglyoxylates in the presence of K2S2O8at 80 °C under metal-free neutral conditions have been investigated, which extended a platform for the tandem synthesis of nitrogen heterocycles. While arylglyoxylic acids are known to undergo decarboxylation to form an acyl radical in the presence of K2S2O8and used in the Minisci acylation of electron-deficient (hetero)aromatics, their reactions with electron-richortho-substituted anilines to form nitrogen heterocycles have recently been studied. Depending upon the experimental conditions used in the reactions, the mechanism of the formation of heterocycles involving reactions of an acyl radical or aryl iminocarboxylic acids has been postulated. Given the subtle understanding of the mechanisms of annulation reactions of 2-substituted anilines and arylglyoxylates in the presence of K2S2O8, an extensive mechanistic investigation was undertaken. In the current study, the various mechanistic pathways including the generation of acyl, imidoyl, aminal, and N,O-hemiketal radicals have been postulated based on different possible decarboxylation modes. Some of the proposed intermediates are supported based on the available analytical data. The protocol uses a single, inexpensive reagent K2S2O8, which offers not only transition-metal-free conditions but also serves as the reagent for the key decarboxylation step. Taken together, this study complements the current development of the annulation reactions of 2-substituted anilines and arylglyoxylates in terms of synthesis and mechanistic understanding.
- Laha, Joydev K.,Panday, Surabhi,Tomar, Monika,Patel, Ketul V.
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supporting information
p. 845 - 853
(2021/02/09)
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- Lewis-acid-promoted cyclization reaction: Synthesis of N3-chloroethyl and N3-thiocyanatoethyl quinazolinones
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A Lewis-acid-promoted cyclization reaction of benzoyl chlorides with 2-(4,5-dihydrooxazol-2-yl)anilines, which can offer a series of N3-chloroethyl quinazolinones, is disclosed. The reaction is compatible with the functional groups of the substrates; environment-friendly AlCl3 is probably the chloride source. Moreover, the addition of NH4SCN can also produce a range of N3-thiocyanatoethyl quinazolinones in moderate-to-good yields.
- Hu, Fang-Peng,Zhang, Ming-Ming,Huang, Guo-Sheng
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supporting information
p. 9315 - 9319
(2021/06/14)
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- Method for preparing 2 -phenyl quinazolinone compound
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The invention relates to a preparation method of 2 -phenyl quinazolinone compounds, in particular to II. To the method, 2 - (benzylamino) benzamide compound (I) is used as a raw material for reaction of the experiment model, a simple substance iodine cata
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Paragraph 0019-0023
(2021/10/30)
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- Method for synthesizing 2 -phenylquinazolone compound by taking styrene compound as raw material
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The invention discloses a method for synthesizing a 2-phenyl quinazolinone compound. The method comprises the steps of adopting a styrene compound and 2-aminobenzamide as reaction raw materials; underthe combined action of a palladium catalyst, a ligand and oxygen, reacting to obtain the 2-phenyl quinazolinone compound, wherein the reaction temperature is 80 DEG C to 110 DEG C, a reaction formulais as shown in the below figure, and R is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, nitro or methoxyl. The method provided by the invention has the beneficial effects that the raw material styrene compound is cheap and easy to get, so that the method is more economical; a preparation method is simple and convenient to operate, and the obtained product is easy to post-process, so that the method is suitable for large-scale industrial production; no high temperature and high pressure is needed, and a reaction condition is mild; the method is short in reaction time, high efficient to react, high in yield, and higher in reaction efficiency after reaction amplification.
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Paragraph 0032-0046; 0117-0135
(2021/03/03)
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- Preparation method of quinazolinone derivative
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The invention discloses a preparation method of a quinazolinone derivative, wherein the preparation method comprises the following steps: dissolving an anthranilonitrile compound represented by a formula I and an aldehyde represented by a formula II in a
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Paragraph 0023-0026; 0098-0106
(2021/04/14)
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- Copper-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Nitrobenzaldehydes with Aldehydes: Application toward the Synthesis of Natural Products
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A novel, efficient, and atom-economical approach for the construction of quinazolinones from 2-nitrobenzaldehydes has been unveiled via copper-catalyzed nitrile formation, hydrolysis, and reduction in one pot for the first time. In this reaction, urea is used as a source of nitrogen for nitrile formation, hydrazine hydrate is used for both the reduction of the nitro group and the hydrolysis of nitrile, and atmospheric oxygen is used as the sole oxidant. The method portrays a wide substrate scope with good functional group tolerances. Moreover, this method was applied for the synthesis of schizocommunin, tryptanthrin, phaitanthrin-A, phaitanthrin-B, and 8H-quinazolino[4,3-b]quinazolin-8-one.
- Pal, Shantanu,Sahoo, Subrata
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p. 18067 - 18080
(2021/12/06)
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- Diversity in Heterocycle Synthesis Using α-Iminocarboxylic Acids: Decarboxylation Dichotomy
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Despite the structural similarity with imines, α-iminocarboxylic acids have seldom been used in heterocycles synthesis. The reactions of ortho-substituted anilines and arylglyoxylic acids in DMSO at 40 °C gave various benzo-fused five- to six-membered N-heterocycles in good to excellent yields. The reaction proceeds via intramolecular Michael addition of α-iminocarboxylic acids, generated in situ, with an ortho-substituted nucleophile, yielding an isolable unprecedented tetrahedral carboxylic acids, which upon decarboxylation without any aid of additional reagents forms the N-heterocycles. DMSO is crucial in this reaction, perhaps because of improved solubility and the ease of decarboxylation of these tetrahedral carboxylic acids. However, a copper-catalyzed reaction of ortho-substituted anilines and 2-bromoarylglyoxylic acids gave a dibenzo-fused seven-membered N-heterocycle under a basic reaction condition. Unlike intramolecular cyclization with α-iminocarboxylic acids in the first case, α-iminocarboxylic acid undergoes a competitive decarboxylation under the copper-catalyzed conditions, which upon subsequent heteroarylation form the heterocycles. Taken together, the study described herein represents two different modes of decarboxylation observed with α-iminocarboxylic acids, leading to the synthesis of divergent heterocycles and pharmaceuticals, which remained unexplored previously.
- Hunjan, Mandeep Kaur,Laha, Joydev K.
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- Discovery of New 4-Indolyl Quinazoline Derivatives as Highly Potent and Orally Bioavailable P-Glycoprotein Inhibitors
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The major drawbacks of P-glycoprotein (P-gp) inhibitors at the clinical stage make the development of new P-gp inhibitors challenging and desirable. In this study, we reported our structure-activity relationship studies of 4-indolyl quinazoline, which led to the discovery of a highly effective and orally active P-gp inhibitor, YS-370. YS-370 effectively reversed multidrug resistance (MDR) to paclitaxel and colchicine in SW620/AD300 and HEK293T-ABCB1 cells. YS-370 bound directly to P-gp, did not alter expression or subcellular localization of P-gp in SW620/AD300 cells, but increased the intracellular accumulation of paclitaxel. Furthermore, YS-370 stimulated the P-gp ATPase activity and had moderate inhibition against CYP3A4. Significantly, oral administration of YS-370 in combination with paclitaxel achieved much stronger antitumor activity in a xenograft model bearing SW620/Ad300 cells than either drug alone. Taken together, our data demonstrate that YS-370 is a promising P-gp inhibitor capable of overcoming MDR and represents a unique scaffold for the development of new P-gp inhibitors.
- Chen, Zhe-Sheng,Dai, Qing-Qing,Li, Guo-Bo,Liu, Hong-Min,Liu, Hui,Wang, Bo,Wang, Shaomeng,Yu, Bin,Yuan, Shuo,Zhang, Jing-Ya,Zhang, Xiao-Nan,Zuo, Jia-Hui
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p. 14895 - 14911
(2021/10/12)
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- Direct Use of Benzylic Alcohols for Multicomponent Synthesis of 2-Aryl Quinazolinones Utilizing the π-Benzylpalladium(II) System in Water
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We demonstrate the direct use of benzylic alcohols for a multicomponent reaction of readily available isatoic anhydrides with amines in water, which is a synthetic route for the direct construction of a series of 2-aryl quinazolinones. This one-pot synthetic method involves the dehydrative N-benzylation of in situ generated anthranilamides followed by an amide-directed benzylic C?H amination process utilizing the π-benzylPd(II) system. Comparison of independent rate measurements using benzyl alcohol and its deuterated form gave a kinetic isotope effect of 3.5. Therefore, the benzylic C?H bond is cleaved in the rate-determining step. We successfully carried out a gram-scale reaction in 85% yield with simplified product isolation. (Figure presented.).
- Hikawa, Hidemasa,Nakayama, Taku,Takahashi, Makiko,Kikkawa, Shoko,Azumaya, Isao
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supporting information
p. 4075 - 4084
(2021/07/26)
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- Ammonium formate-Pd/C as a new reducing system for 1,2,4-oxadiazoles. Synthesis of guanidine derivatives and reductive rearrangement to quinazolin-4-ones with potential anti-diabetic activity
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1,2,4-Oxadiazole is a heterocycle with wide reactivity and many useful applications. The reactive O-N bond is usually reduced using molecular hydrogen to obtain amidine derivatives. NH4 CO2 H-Pd/C is here demonstrated as a new system for the O-N reduction, allowing us to obtain differently substituted acylamidine, acylguanidine and diacylguanidine derivatives. The proposed system is also effective for the achievement of a reductive rearrangement of 5-(2′-aminophenyl)-1,2,4-oxadiazoles into 1-alkylquinazolin-4(1H)-ones. The alkaloid glycosine was also obtained with this method. The obtained compounds were preliminarily tested for their biological activity in terms of their cytotoxicity, induced oxidative stress, α-glucosidase and DPP4 inhibition, showing potential application as anti-diabetics.
- Buscemi, Silvestre,Marzullo, Paola,Nuzzo, Domenico,Pace, Andrea,Piccionello, Antonio Palumbo,Vasto, Sonya
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- K2S2O8activation by glucose at room temperature for the synthesis and functionalization of heterocycles in water
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While persulfate activation at room temperature using glucose has primarily been focused on kinetic studies of the sulfate radical anion, the utilization of this protocol in organic synthesis is rarely demonstrated. We reinvestigated selected K2S2O8-mediated known organic reactions that invariably require higher temperatures and an organic solvent. A diverse, mild functionalization and synthesis of heterocycles using the inexpensive oxidant K2S2O8 in water at room temperature is reported, demonstrating the sustainability and broad scope of the method. Unlike traditional methods used for persulfate activation, the current method uses naturally abundant glucose as a K2S2O8 activator, avoiding the use of higher temperature, UV light, transition metals or bases.
- Hunjan, Mandeep Kaur,Laha, Joydev K.
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p. 8437 - 8440
(2021/09/02)
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- Metal-free synthesis of 1,4-benzodiazepines and quinazolinones from hexafluoroisopropyl 2-aminobenzoates at room temperature
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Herein, we describe the novel reactivity of hexafluoroisopropyl 2-aminobenzoates. The metal-free synthesis of 1,4-benzodiazepines and quinazolinones from hexafluoroisopropyl 2-aminobenzoates has been developed at room temperature. These procedures feature
- Chen, Jiewen,Liang, En,Shi, Jie,Wu, Yinrong,Wen, Kangmei,Yao, Xingang,Tang, Xiaodong
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p. 4966 - 4970
(2021/02/06)
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- Ruthenium(II)-catalyzed C?C/C?N coupling of 2-arylquinazolinones with vinylene carbonate: Access to fused quinazolinones
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In this work, ruthenium(II)-catalyzed C?C/C?N annulation of 2-arylquinazolinones with vinylene carbonate is reported to synthesize fused quinazolinones. This catalytic system tolerates a wide range of substrates with excellent functional-group compatibility. In this transformation, the vinylene carbonate acts as an ethynol surrogate without any external oxidant involved. Furthermore, preliminary mechanistic studies were conducted, and a plausible catalytic cycle was also proposed.
- Wang, Zhao-Hui,Wang, He,Wang, Hua,Li, Lei,Zhou, Ming-Dong
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supporting information
p. 995 - 999
(2021/03/03)
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- Pd/C Catalyzed Cascade Synthesis of 2-Arylquinazolinones from 2-Iodoacetanilides Employing Ammonia and CO Precursors
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An efficient and straightforward approach has been demonstrated for 2-aryl quinazolinones synthesis from 2-iodoacetanilides using ammonium carbamate/ammonium carbonate and oxalic acid under heterogeneous Pd/C catalyzed conditions. Herein, we have carried
- Shaifali,Mehara, Pushkar,Kumar, Ashish,Das, Pralay
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p. 2459 - 2464
(2021/03/31)
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- Direct synthesis of quinazolinones via the carbon-supported acid-catalyzed cascade reaction of isatoic anhydrides with amides and aldehydes
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A novel catalytic system is reported for the construction of quinazolinones via the carbon-supported acid-catalyzed cascade coupling of isatoic anhydrides with amides and aldehydes. Subsequent selective hydrosilylation of the quinazolinones using a hydrogen-transfer strategy was also explored to provide dihydroquinazolines with structural diversity. The developed methodology proceeds with a broad substrate scope, excellent functional group tolerance, and utilizes a reusable catalyst and air as a green oxidant.
- Zhang, Xiangyu,Luo, Chujun,Chen, Xiaoyong,Ma, Weilin,Li, Bin,Lin, Zirui,Chen, Xiuwen,Li, Yibiao,Xie, Feng
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supporting information
(2021/02/20)
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