1022-45-3Relevant articles and documents
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
Sun, Jinwei,Tao, Tao,Xu, Dan,Cao, Hui,Kong, Qinggang,Wang, Xinyu,Liu, Yun,Zhao, Jianglin,Wang, Yi,Pan, Yi
, p. 2099 - 2102 (2018)
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.
A recyclable CuO-catalyzed synthesis of 4(3H)-quinazolinones
Zhan, Dan,Li, Tianbin,Wei, Haidong,Weng, Wen,Ghandi, Khashayar,Zeng, Qingle
, p. 9325 - 9329 (2013)
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.
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Endicott et al.
, p. 1299 (1946)
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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
Sharma, Rohit,Vishwakarma, Ram A.,Bharate, Sandip B.
, p. 3027 - 3033 (2016)
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.).
Electron transfer-induced oxidation of 2,3-dihydroquinazolin-4(1H)-ones
Memarian, Hamid Reza,Ghahremani, Saeideh
, p. 403 - 408 (2017)
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.
Q-Tube assisted MCRs for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones
Sancineto, Luca,Monti, Bonifacio,Merlino, Orsola,Rosati, Ornelio,Santi, Claudio
, p. 270 - 278 (2018)
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.
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
Ram, Shankar,Shaifali,Chauhan, Arvind Singh,Sheetal,Sharma, Ajay Kumar,Das, Pralay
, p. 14506 - 14511 (2019)
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
Quinazolinones from o-Aminobenzonitriles by One-Pot Sequential Selective Hydration/Condensation/Acceptorless Dehydrogenation Catalyzed by an Iridium Complex
Zhao, Wei,Liu, Pengcheng,Li, Feng
, p. 1523 - 1530 (2016)
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.
One-pot synthesis of quinazolinones via iridium-catalyzed hydrogen transfers
Zhou, Jianguang,Fang, Jie
, p. 7730 - 7736 (2011)
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.
A magnetically retrievable copper ionic liquid nanocatalyst for cyclooxidative synthesis of 2-phenylquinazolin-4(3: H)-ones
Gupta, Radhika,Arora, Gunjan,Yadav, Priya,Dixit, Ranjana,Srivastava, Anju,Sharma, Rakesh Kumar
, p. 890 - 898 (2021)
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.
Copper (II)-supported polyethylenimine-functionalized magnetic graphene oxide as a catalyst for the green synthesis of 2-arylquinazolin-4(3H)-ones
Sayahi, Mohammad Hosein,Bahadorikhalili, Saeed,Saghanezhad, Seyyed Jafar,Mahdavi, Mohammad
, p. 5241 - 5253 (2018)
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.
Bronsted acidic ionic liquids: New, efficient, and green promoter system for the synthesis of 4(3H)-quinazolinones
Heravi, Majid M.,Tavakoli-Hoseini, Niloofar,Bamoharram, Fatemeh F.
, p. 707 - 714 (2011)
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.
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
Davoodnia,Allameh,Fakhari,Tavakoli-Hoseini
, p. 550 - 553 (2010)
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.
Potassium hydroxide-promoted transition-metal-free synthesis of 4(3H)-quinazolinones
Qiu, Dezhi,Wang, Yanyan,Lu, Dongming,Zhou, Lihong,Zeng, Qingle
, p. 1343 - 1347 (2015)
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.]
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
Shokri, Zahra,Azimi, Nahid,Moradi, Sirvan,Rostami, Amin
, (2020)
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
Y(OTf)3-catalyzed heterocyclic formation via aerobic oxygenation: An approach to dihydro quinazolinones and quinazolinones
Shang, Ying-Hui,Fan, Li-Yan,Li, Xiang-Xiong,Liu, Meng-Xia
, p. 1355 - 1358 (2015)
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.
Br?nsted acid catalyzed synthesis of 2‐aryl‐quinazolinones via cyclization of 2‐aminobenzamide with benzonitriles in PEG
Matcha, Sowbhagya Lakshmi,Karasala, Bharat Kumar,Botsa, Sathish Mohan,Vidavalur, Siddaiah
, p. 1955 - 1961 (2021)
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.
Vanadium-catalyzed synthesis of 4(3H)-quinazolinones from anthranilamides and aryl aldehydes
Zhan, Dan,Li, Tianbin,Zhang, Xiaoping,Dai, Chuan,Wei, Haidong,Zhang, Yuyu,Zeng, Qingle
, p. 2493 - 2500 (2013)
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
Synthesis, antimicrobial and nematicidal evaluation of a new class of triazolo[4,3-c]quinazolinylthiazolidinones
Sanjeeva Reddy, Cherkupally,Rajesh Kumar, Gaddam,Sunitha, Bommineni
, p. 923 - 931 (2016)
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.
Light induced oxidation of 2,3-dihydroquinazolin-4(1H)-ones
Memarian, Hamid R.,Ebrahimi, Saeid
, p. 8 - 15 (2013)
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
Simple, selective, and practical synthesis of 2-substituted 4(3H)-quinazolinones by Yb(OTf)3-catalyzed condensation of 2-aminobenzamide with carboxamides
Yoshimura, Tsutomu,Yuanjun, Di,Kimura, Yu,Yamada, Hisatsugu,Toshimitsu, Akio,Kondo, Teruyuki
, p. 857 - 865 (2015)
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.
Aerobic photooxidative synthesis of 2-aryl-4-quinazolinones from aromatic aldehydes and aminobenzamide using catalytic amounts of molecular iodine
Nagasawa,Matsusaki,Nobuta,Tada,Miura,Itoh
, p. 63952 - 63954 (2015)
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.
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Yoneda et al.
, p. 359 (1973)
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Synthesis, biological evaluation and molecular modelling insights of 2-arylquinazoline benzamide derivatives as anti-tubercular agents
Ahmad, Md Naiyaz,Akhir, Abdul,Chopra, Sidharth,Gatadi, Srikanth,Gour, Jitendra,Kaul, Grace,Madhavi, Y. V.,Malasala, Satyaveni,Nanduri, Srinivas,Shukla, Manjulika
, (2020)
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.
Survey Reactivity of Some Substituted Quinazolinones with Pentafluoro(chloro)pyridine
Ranjbar-Karimi, Reza,Davodian, Tayebeh,Mehrabi, Hossein
, p. 475 - 480 (2018)
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.
N^N^O hydrazone capped pincer type palladium complex catalysed construction of quinazolinones from alcohols
Anandaraj, Pennamuthiriyan,Kamatchi, Thangavel Sathiya,Ramesh, Rengan
, (2022/01/11)
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.
Access to 2-Arylquinazolin-4(3H)-ones through Intramolecular Oxidative C(sp3)?H/N?H Cross-Coupling Mediated by I2/DMSO
Wen, Simiaomiao,Du, Yifan,Liu, Yiwen,Cui, Xiaofeng,Liu, Qixing,Zhou, Haifeng
, (2021/12/01)
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.
Zinc Stabilized Azo-anion Radical in Dehydrogenative Synthesis of N-Heterocycles. An Exclusively Ligand Centered Redox Controlled Approach
Das, Siuli,Mondal, Rakesh,Chakraborty, Gargi,Guin, Amit Kumar,Das, Abhishek,Paul, Nanda D.
, p. 7498 - 7512 (2021/06/30)
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.
