- Aziridination of α,β-unsaturated esters bearing allylic hydroxy groups with 3-acetoxyaminoquinazolinones: Evidence for a mechanism comprising Michael addition-SN2 nucleophilic displacement of acetoxy for aziridination of α,β-unsaturated esters
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Aziridinations of the allylic alcohol-bearing α,β-unsaturated esters 6 and 7 and their corresponding acetates 8 and 9 have been carried out under standard conditions using 3-acetoxyaminoquinazolinone 2. Whereas the preferred sense of diastereoselectivity
- Atkinson, Robert S.,Williams, Paul J.
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Read Online
- Substrate-controlled diastereoselective aziridination of alkenes using 3-acetoxyaminoquinazolinone in the presence of hexamethyldisilazane
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8-Phenylmenthol derived α,β-unsaturated esters were aziridinated highly diastereoselectively using 3-acetoxyamino-2-ethylquinazolinone. The yields of these aziridines were greatly improved in the presence of hexamethyldisilazane.
- Ulukanli, Sabri,Karabuga, Semistan,Celik, Ayhan,Kazaz, Cavit
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- Aziridination of Electron-rich Acyclic Allylic alcohols using 3-Acetoxyaminoquinazolinones
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The products from aziridination of the phenyl-substituted allylic alcohols 6 and 7 with 3-acetoxyaminoquinazolinones 1 and 15 have been compared with those from aziridination of the methyl ester analogues 2, and 3: the differences in diastereoselectivities using these electron-rich and electron-deficient alkenes are ascribed to the intervention of transition states 8 and 4 respectively.
- Atkinson, Robert S.,Fawcett, John,Russell, David R.,Williams, Paul J.
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- AZIRIDINATION OF ALKENES BY 3-AMINO-2-ETHYLQUINAZOLIN-3H-4-ONE AND LEAD TETRA-ACETATE-TRIFLUOROACETIC ACID
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A number of alkenes undergo aziridination in good yield by oxidative addition of the title N-aminoquinazolone (1) only in the presence of TFA.
- Atkinson, Robert S.,Darrah, Christine M.,Kelly, Brian J.
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- Imination of sulfoxides using 3-acetoxyaminoquinazolinone as nitrogen source in the presence of hexamethyldisilazane
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The reaction of 3-acetoxyaminoquinazolinone (QNHOAc) with various sulfoxides in the presence of HMDS as an acetic acid scavenger, afforded the corresponding sulfoximides in good yields. Sulfoximidation of phenyl methyl sulfoxide using a Q*NHOAc having a s
- Karabuga, Semistan,Kazaz, Cavit,Kilic, Hamdullah,Ulukanli, Sabri,Celik, Ayhan
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Read Online
- Visible-light- And bromide-mediated photoredox Minisci alkylation of N-heteroarenes with ester acetates
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A visible-light-induced photoredox Minisci alkylation reaction of N-heteroarenes with ethyl acetate has been reported. The low-toxic ethyl acetate was used for the first time as an alkylation reagent. Hence, 4-quinazolinones, quinolines and pyridines reacted smoothly in the current reaction system. Mechanistic studies indicate that LiBr plays a key role to dramatically improve the efficiency of the reaction by the mediation of hydrogen atom transfer. This journal is
- Deng, Guo-Jun,Huang, Huawen,Shi, Hang,Wang, Chunlian
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supporting information
p. 9177 - 9181
(2021/11/16)
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- Synthesis and in vitro antileishmanial efficacy of novel quinazolinone derivatives
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Currently available drugs being used to treat leishmaniasis have several shortcomings, including high toxicity, drug administration that requires hospitalization, and the emergence of parasite resistance against clinically used drugs. As a result, there is a dire need for the development of new antileishmanial drugs that are safe, affordable, and efficient. In this study, two new series of synthesized quinazolinone derivatives were investigated as potential future antileishmanial agents, by assessing their activities against the Leishmania (L.) donovani and L.?major species. The cytotoxicity profiles of these derivatives were assessed in vitro on Vero cells. The compounds were found to be safer and without any toxic activities against mammalian cells, compared to the reference drug, halofuginone, a clinical derivative of febrifugine. However, they had demonstrated poor antileishmanial growth inhibition efficacies. The two compounds that had been found the most active were the mono quinazolinone 2d and the bisquinazolinone 5b with growth inhibitory efficacies of 35% and 29% for the L.?major and L.?donovani 9515 promastigotes, respectively. These outcomes had suggested structural redesign, inter alia the inclusion of polar groups on the quinazolinone ring, to potentially generate novel quinazolinone derivatives, endowed with effective antileishmanial potential.
- Prinsloo, Izak F.,Zuma, Nonkululeko H.,Aucamp, Janine,N’Da, David D.
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p. 383 - 398
(2020/09/23)
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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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supporting information
p. 1427 - 1431
(2020/11/02)
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- Cobalt-Catalyzed Tandem Transformation of 2-Aminobenzonitriles to Quinazolinones Using Hydration and Dehydrogenative Coupling Strategy
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A tandem synthesis of quinazolinones from 2-aminobenzonitriles is demonstrated here by using an aliphatic alcohol-water system. For this transformation, a cheap and easily available cobalt salt and P(CH2CH2PPh2)3 (PP3) ligand were employed. The substrate scope, scalability, and synthesis of natural products exhibited the vitality of this protocol.
- Samim, Sk. Abdus,Roy, Bivas Chandra,Nayak, Sourav,Kundu, Sabuj
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p. 11359 - 11367
(2020/10/12)
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- Imidazolium chloride as an additive for synthesis of 4(3H)-quinazolinones using anthranilamides and DMF derivatives
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Imidazolium chloride as an environmentally benign additive efficiently facilitates construction of 4(3H)-quinazolinones using anthranilamides and DMF derivatives. A series of 4(3H)-quinazolinones were prepared in moderate to excellent yields without conventional oxidants, metal catalysts and corrosive acids or other additives.
- Dai, Zeshu,Li, Dan,Li, Zhiyao,Liu, Heng,Luo, Wen,Shang, Suqin,Tian, Qingqiang,Wang, Shuqi,Wang, Xuetong,Wang, Yin,Wu, Huili,Xiao, Xin,Yuan, Jianyong,Zhou, Shangjun
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- Copper-Catalyzed Intramolecular α-C-H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis
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A copper-catalyzed intramolecular α-C-H amination has been developed for the synthesis of quinazolin-4(3 H)-one derivatives from commercially available isatoic anhydride and primary and secondary benzylamines via ring-opening cyclization (ROC). This method shows good functional group tolerance and allows access to a range of 2-aryl, 2-alkyl, and spiroquinazolinone derivatives. However, 2-methylquinazolin-4(3 H)-one was synthesized from 2-amino- N -isopropylbenzamide by C-C bond cleavage, and N -benzyl-2-(methylamino)benzamide afforded 1-methyl-2-phenylquinazolin-4(1 H)-one along with 2-phenylquinazolin-4(3 H)-one by N-C bond cleavage for aromatization. It is the first general method to construct the potentially useful 2-methylquinazolin-4(3 H)-one by copper-catalyzed intramolecular C-H amination. Also this ROC strategy has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.
- Biswal, Sonali,Chada, Harika,Patel, Srilaxmi M.,Sharada, Duddu S.,Sharma, Sonika
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p. 3160 - 3170
(2019/08/07)
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- Synthesis and evaluation of chalcone analogues containing a 4-oxoquinazolin-2-yl group as potential anti-tumor agents
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The chalcone motif can be found in many molecules that contribute to essential biological processes, and many chalcone-containing compounds exhibit potent anti-cancer activity. Here, we synthesized two series of chalcone analogues (3a?s and 6a?s) based on substituting the chalcone B-ring or A-ring with a 4-oxoquinazolin-2-yl group, and then evaluated them for cytotoxic activity in human colorectal HCT-116 and breast cancer MCF-7 cell lines. Compounds 3a?s (in which a 4-oxoquinazolin-2-yl group functioned as the B-ring) were markedly more cytotoxic than compounds 6a?s (in which 4-oxoquinazolin-2-yl group functioned as the A-ring), based on their IC50 values to inhibit proliferation. Compound 3f was found as the most potent among 38 analogues and the mechanism of its cytotoxicity was investigated. Flow cytometry indicated that HCT-116 cells treated with compound 3f resulted in a dose-dependent accumulation of cells in the sub-G1 phase, which is representative of apoptotic cells. Subsequent assays (including Annexin V-FITC/PI, AO-EB, MitoSOX Red and JC-1 staining) confirmed that 3f exposure induced apoptosis in HCT-116 cells. Immunoblotting analysis indicated that cellular exposure to 3f increased the cleavage of PARP1 and caspases 3, 7, and 9. Taken together, this novel chalcone analogue has a cytotoxic effect on cultured cancer cell-lines that is likely mediated by inducing apoptosis via the mitochondrial death pathway.
- Han, Xue,Peng, Bin,Xiao, Bei-Bei,Cao, S.-Li,Yang, Chao-Rui,Wang, Wen-Zhu,Wang, Fu-Cheng,Li, Hong-Yun,Yuan, Xiao-Li,Shi, Ruifeng,Liao, Ji,Wang, Hailong,Li, Jing,Xu, Xingzhi
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p. 586 - 601
(2018/11/26)
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- Method for preparing quinazolinone from enol
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The invention discloses a method for preparing a quinazolinone derivative from enol. According to the method, a relatively inexpensive ruthenium complex is used as a catalyst in a reaction to catalyzea microwave reaction of commercial and easily-available 2-aminobenzamide with enol for the preparation of quinazolinone. Compared with conventional synthesis methods for quinazolinone of the same kind, the method of the invention has the following advantages: no alkali is used in the reaction process; clean and non-toxic tetrahydrofuran is used as a reaction solvent; hydrogen is automatically transferred, and the atom economy of the reaction is high; and the by-product of the invention is only water.
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Paragraph 0029-0033
(2019/03/15)
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- A in ammonia water condition of microwave halo benzoic acid synthesis method of the quinazoline compounds
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The invention discloses a in ammonia water condition of microwave halo benzoic acid synthetic quinazoline compounds of the method, the use of palladium chloride to serve as the catalyst, in ammonia water under the microwave heating condition, neighbouring halogen benzoic acid generated by the reaction with the isocyanate of the quinazoline compounds of the method, the invention an environment-friendly, the operation is simple, cheap and safe, efficient process for producing quinazoline compounds of the method. Compared with the prior art, this method not only can be applied to a large number of functional groups, the productive rate is high, few by-products, and the operation is simple, safe, low cost, environmental protection.
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Paragraph 0017; 0027
(2019/02/13)
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- A in the aqueous phase under microwave conditions using halogenated benzamide fast synthesis of quinazoline compounds of the method
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The invention discloses a in the aqueous phase under microwave conditions using halogenated benzamide fast synthesis of quinazoline compounds of the method, the use of palladium chloride to serve as the catalyst, in water under microwave heating conditions, neighbouring halogen benzamide with an isocyanate reaction to produce the quinazoline compounds of the method, the invention an environment-friendly, the operation is simple, cheap and safe, efficient process for producing quinazoline compounds of the method. Compared with the prior art, this method not only can be applied to a large number of functional groups, the productive rate is high, few by-products, and the operation is simple, safe, low cost, environmental protection.
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Paragraph 0015; 0025
(2019/02/13)
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- Quinazolin-4(3H)-ones and 5,6-dihydropyrimidin-4(3H)-ones from β-aminoamides and orthoesters
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Quinazolin-4(3H)-ones have been prepared in one step from 2-aminobenzamides and orthoesters in the presence of acetic acid. Simple 2-aminobenzamides were easily converted to the heterocycles by refluxing in absolute ethanol with 1.5 equivalents of the orthoester and 2 equivalents of acetic acid for 12–24 h. Ring-substituted and hindered 2-aminobenzamides as well as cases incorporating an additional basic nitrogen required pressure tube conditions with 3 equivalents each of the orthoester and acetic acid in ethanol at 110?C for 12–72 h. The reaction was tolerant towards functionality on the benzamide and a range of structures was accessible. Workup involved removal of the solvent under vacuum and either recrystallization from ethanol or trituration with ether-pentane. Several 5,6-dihydropyrimidin-4(3H)-ones were also prepared from 3-amino-2,2-dimethylpropionamide. All products were characterized by melting point, FT-IR, 1H-NMR, 13C-NMR, and HRMS.
- Gavin, Joshua T.,Annor-Gyamfi, Joel K.,Bunce, Richard A.
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- Design, synthesis and biological evaluation of novel bouchardatine analogs as potential inhibitors of adipogenesis/lipogenesis in 3T3-L1 adipocytes
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Inhibition of the differentiation of adipocytes and reduced lipid synthesis are efficacious approaches for treating obesity-related metabolic disorders. Bouchardatine (Bou) is a natural alkaloid that has been reported to moderately inhibit the differentiation of 3T3-L1 cells without inducing toxicity. To explore the importance of aldehyde group at 8a-position of Bou and optimize the activity, we synthesized 35 (31 novel) compounds by discarding or replacing aldehyde group with halogen and introducing different amine chains at 5-position of Bou. The lipid-lowering activity was evaluated using a cell-based screening system. The substitution of the group at the 8a-position of compounds was important for its lipid-lowering activity, and the SAR was discussed. The selective compound 6e showed a 93-fold increase in its lipid-lowering effect (EC50 = 0.24 μM) compared with Bou (EC50 ≈ 25 μM). Further mechanistic studies revealed that compound 6e activated AMP-activated protein kinase (AMPK) pathway and inhibited MCE activity to block cell proliferation and induce cell cycle arrest at the early stage of differentiation, thus decreasing the expression of adipogenic factors and fatty acid synthesis-related proteins.
- Gao, Lin,Xu, Zhao,Rao, Yong,Lu, Yu-Ting,Hu, Yu-Tao,Yu, Hong,Xu, Yao-Hao,Song, Qing-Qing,Ye, Ji-Ming,Huang, Zhi-Shu
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- Lewis-Acid-Catalysed Activation of Nitriles: A Microwave-Assisted Solvent-Free Synthesis of 2,4-Disubstituted Quinazolines and 1,3-Diazaspiro[5.5]undec-1-enes
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Two different modes of cyclization take place to synthesize quinazoline, quinazolinone, and 1,3-diazaspiro[5.5]undec-1-ene derivatives through the Lewis-acid-catalysed activation of both aliphatic and aromatic nitriles in a single-step, solvent-free, and transition-metal-free reaction. An amidine is expected to form as an intermediate; this then undergoes intramolecular cyclization in a one-pot reaction sequence. The reaction is carried out under microwave irradiation using trimethylsilyltrifluoromethane sulfonate (TMSOTf) as a catalyst and nitriles as a nitrogen source with the respective reaction partners.
- Saikia, Ujwal Pratim,Borah, Geetika,Pahari, Pallab
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supporting information
p. 1211 - 1217
(2018/03/21)
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- Facile and solvent-free synthesis of quinazolin-4(3H)-ones under microwave condition promoted by SbCl3
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– Antimony trichloride (SbCl3) was found to be an effective catalyst (1 mol%) for one-pot synthesis of quinazolin-4(3H)-ones in good to excellent yields using anthranilamide and acyl chlorides under microwave irradiation. This method has the advantages of simplicity, mild reaction conditions, highly tolerant to several functional groups, as well as the avoidance of hazardous solvents.
- Li, Jun,Wang, Weili,Su, Xinglin,Zhang, Xiaoling,Zhang, Yan,Zhang, Xuewen,Cai, Mengmeng,Cao, Yuqian,Jin, Juan,Xu, Yanbin
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p. 2107 - 2110
(2019/04/04)
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- Synthesis of some novel quinazolin-4(3H)-one hybrid molecules as potent urease inhibitors
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A new series of quinazolinone hybrid molecules containing coumarin, furan, 1,2,4-triazole and 1,2,4-thiadiazole rings was designed, synthesized, and screened for their urease inhibition activities. All newly synthesized compounds showed outstanding urease inhibitory potentials with IC50 values ranging between 1.26 ± 0.07 and 7.35 ± 0.31 μg/mL. Among the series, coumarin derivatives (10a–d) exhibited the best inhibitory effect against urease in the range of IC50 = 1.26 ± 0.07 to 1.82 ± 0.10 μg/mL, when compared to standard urease inhibitors such as acetohydroxamic acid and thiourea (IC50 = 21.05 ± 0.96 and 15.08 ± 0.71 μg/mL, respectively). Molecular docking studies were also performed to analyze the binding mode of compound 10b, and supported the experimental results.
- Mente?e, Emre,Akyüz, Gülay,Y?lmaz, Fatih,Balta?, Nimet,Emirik, Mustafa
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- Auto-Tandem Catalysis with Ruthenium: From o-Aminobenzamides and Allylic Alcohols to Quinazolinones via Redox Isomerization/Acceptorless Dehydrogenation
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A strategy for the synthesis of quinazolinones via Ru-catalyzed redox isomerization/acceptorless dehydrogenation was proposed and accomplished. In the presence of a commercially available [(p-cymene)Cl2]2, a range of desirable products were obtained with o-aminobenzamides and allylic alcohols as starting materials in moderate to high yields. This strategy is attractive due to high atom efficiency, and minimal consumption of chemicals and energy. (Figure presented.).
- Zhang, Weikang,Meng, Chong,Liu, Yan,Tang, Yawen,Li, Feng
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p. 3751 - 3759
(2018/09/14)
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- The Synthesis of Quinazolinones from Olefins, CO, and Amines over a Heterogeneous Ru-clusters/Ceria Catalyst
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Quinazolinones, an important class of heterocyclic compounds, have been widely used in pharmaceuticals because of their biological activity. However, the efficient and economical synthesis of quinazolinones has remained a challenge. A novel synthetic approach has now been developed to produce quinazolinones from olefins, CO, and amines over heterogeneous Ru-clusters/ceria catalyst in the absence of acids, bases, and oxidants. Furthermore, H2O is generated as the only by-product. A series of quinazolinones with aromatic or non-aromatic substituents can be obtained in yields of up to 99 %. The Ru-clusters/ceria can be reused at least four times. The analysis of the E-factor (environmental impact factor) for the synthesis of 2-ethyl quinazolinone suggests that this system is more environmentally friendly than other processes reported previously.
- An, Jinghua,Wang, Yehong,Zhang, Zhixin,Zhao, Zhitong,Zhang, Jian,Wang, Feng
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supporting information
p. 12308 - 12312
(2018/09/06)
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- Quinazolinone compound preparation method
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The present invention relates to a quinazolinone compound preparation method, wherein a quinazolinone-based compound is prepared by using 2-aminobenzamide, olefin and carbon monoxide as reaction substrates and using tetrahydrofuran as a solvent under the catalysis effect of a ruthenium loaded metal oxide. The reaction process comprises: adding tetrahydrofuran, 2-aminobenzamide, olefin and a catalyst into a pressure container, inflating with carbon monoxide, sealing, stirring, and carrying out a reaction for not less than 0.5 h at a reaction temperature of not lower than 120 DEG C, wherein thecatalyst is easily separated from the reaction system after the reaction, and can be recycled multiple times, and the yield of the quinazolinone-based compound is up to 100%.
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Paragraph 0044-0074; 0081-0086
(2018/09/28)
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- 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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p. 2099 - 2102
(2018/05/04)
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- Microwave-assisted synthesis of quinazolin-4(3H)-ones catalyzed by SbCl
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Antimony(III) trichloride (SbCl3) is an effective catalyst (1 mol%) for the condensation of anthranilic amide with various aldehydes or ketones to quinazolin-4(3H)-one derivatives in good to excellent yields under microwave irradiation. The process is carried out within several minutes under solvent-free conditions. This general methodology has the advantages of simplicity, mild reaction conditions and high yields of products.
- Kang, Huaiyuan,Wang, Weili,Sun, Qinqiang,Yang, Shuya,Jin, Juan,Zhang, Xuewen,Ren, Xiaoliang,Zhang, Jiming,Zhou, Jianhua
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p. 293 - 296
(2018/11/27)
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- Phosphorous acid functionalized polyacrylonitrile fibers with a polarity tunable surface micro-environment for one-pot C-C and C-N bond formation reactions
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The preparation and application of fiber catalysts have attracted much attention. However, research on the effect of the micro-environment of fiber catalysts on the catalytic activities though of special importance is limited. In this work, a novel strategy for the synthesis of phosphoric acid-functionalized polyacrylonitrile fibers with a polarity tunable surface micro-environment by hydrophobic groups for one-pot C-C and C-N bond formation reactions is reported. The special hydrophobic surface micro-environment of the fiber catalysts is proven to promote the catalytic activities impressively in cyclocondensation of β-ketoesters with 2-aminobenzamides, the Knoevenagel condensation as well as the multi-component Biginelli reactions in green solvents. Both the surface synergy of the catalytic sites and hydrophobic auxiliary groups (benzyl or n-butyl) in the surface of fiber catalysts and interface acceleration in reaction medium play an important role in the highly efficient promotion of catalytic activity. Thereby a surface synergistic mechanism is proposed to explain the micro-environment effect. In addition, the fiber catalysts could be simply separated from the reaction system using tweezers and directly used in the next cycle without further treatment. Importantly, even after 10 reaction cycles in water or ethanol, there is no significant loss in their catalytic activity. The results indicate that the phosphoric acid functionalized fibers show green and sustainable potential for industrial production.
- Xu, Gang,Wang, Lu,Li, Mengmeng,Tao, Minli,Zhang, Wenqin
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supporting information
p. 5818 - 5830
(2017/12/26)
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- Design, synthesis, molecular modeling and anti-hyperglycemic evaluation of quinazolin-4(3H)-one derivatives as potential PPARγ and SUR agonists
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Peroxisome proliferator-activated receptor gamma (PPARγ) and sulfonylurea receptor (SUR) play crucial roles in management of type-2 diabetes mellitus. In this study, a series of novel quinazoline-4(3H)-one-sulfonylurea hybrids were designed and synthesized as dual PPARγ and SUR agonists. The synthesized compounds were evaluated for their in vivo anti-hyperglycemic activities against STZ-induced hyperglycemic rats. Four compounds (19a, 19d, 19f and 25g) demonstrated potent activities with reduction in blood glucose levels of 40.43, 46.42, 41.23 and 42.50 %, respectively. The most active ten compounds were further evaluated in vitro for their PPARγ binding affinities and insulin-secreting abilities. Compounds 19b, 19d, 19f, 25f and 25g exhibited the highest affinities against PPARγ with IC50 values of 0.371, 0.350, 0.369, 0.408 and 0.353 μM, respectively. In addition, compounds 19d, 19f, and 25d showed the highest insulin-secreting activities with EC50 values of 0.97, 1.01 and 1.15 μM, respectively. Furthermore, molecular docking and pharmacophore generation techniques were carried out to investigate binding patterns and fit values of the designed compounds with PPARγ and SUR, respectively. Also, two QSAR models were generated to explore the structural requirements controlling the different biological activities of the synthesized compounds against PPARγ and SUR.
- Ibrahim, Mohamed K.,Eissa, Ibrahim H.,Alesawy, Mohamed S.,Metwaly, Ahmed M.,Radwan, Mohamed M.,ElSohly, Mahmoud A.
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p. 4723 - 4744
(2017/10/05)
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- A copper-catalyzed Ritter-type cascade via iminoketene for the synthesis of quinazolin-4(3H)-ones and diazocines
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We have developed a copper-catalyzed Ritter-type reaction/cyclization cascade of anthranilic acids and nitriles, affording the quinazolin-4(3H)-ones. The cascade proceeds through a Ritter-type reaction capturing the iminoketene intermediates by nitriles. Furthermore, we found a novel Ritter-type reaction/condensation/intramolecular anti-Markovnikov hydroamination cascade, providing access to functionalized diazocines in one-pot.
- Abe, Takumi,Kida, Koshiro,Yamada, Koji
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supporting information
p. 4362 - 4365
(2017/04/21)
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- A quinazoline compound and its synthesis method
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The invention discloses a synthetic method of a quinazolinone compound. The method can be used for preparing the quinazolinone compound by carrying out reaction at a proper temperature and time by taking a 2-aminobenzamide derivative and a 1, 3-diketone compound as raw materials, taking chiral Bronsted acid or Lewis acid as a catalyst and water and biodegradable ethyl lactate and polyethylene glycol as a mixed solvent. The synthetic method of the quinazolinone compound provided by the invention is mild in reaction condition, low in cost, environment-friendly, high in yield and suitable for industrial production.
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Paragraph 0120-0123
(2017/11/16)
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- Metal-free synthesis of quinazolinones without any additives in water
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Here we report that an excess amount of aldehyde, in particular, aliphatic aldehyde, without any additives, efficiently facilitates the oxidation of aminal intermediates to quinazolinones in pure water.
- Hu, Ben-Quan,Cui, Jie,Wang, Li-Xia,Tang, Ya-Lin,Yang, Luo
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p. 43950 - 43953
(2016/06/09)
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- New facile and solvent-free method for the one-pot synthesis of quinazolin-4(3H)-ones catalyzed by SbCl3 under microwave irradiation
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Efficient and fast condensation of anthranilic amide or anthranilic acid with various orthoesters have been carried out using a catalytic amount of Antimony(III) chloride (SbCl3) under microwave irradiation to afford a series of 2-substituted quinazolin-4(3H)-ones in good to excellent yields under solvent free condition. The reactions have been operated without solvent by one-pot reaction only in several minutes and the reactions have been optimized, such as microwave irradiation power and catalyst charge. Furthermore, ammonium acetate as a nitrogen source in the condition of anthranilic acid is very convenient. Its simplicity, efficiency, mild reaction conditions, high yields of products, easy workup procedure and good generality, make this one-pot procedure interesting for the preparation of different kinds of substituted quinazolin-4(3H)-ones. One of the important features of this methodology is the use of a minimum amount of SbCl3 as an effective Lewis acid catalyst and the avoidance of hazardous organic solvent.
- Wang, Wei-Li,Li, Xiao-Xia,Zhang, Tao,Zhang, Ji-Ming,Zhou, Jian-Hua
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p. 1196 - 1202
(2017/01/25)
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- Chalcone analogue containing 4-oxygen generation quinazoline-2-radical and preparation method and application of chalcone analogue
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The invention discloses a chalcone analogue containing a 4-oxygen generation quinazoline-2-radical as shown in the formula (I), wherein the definition of all substitute radicals can be found in description; besides, the invention further discloses a preparation method of the chalcone analogue. The chalcone analogue as shown in the formula (I) has an inhibition function on cell proliferation of human breast cancer (MFC-7) and human colon cancer (HCT-116) and can be used as anti-tumor medicine.
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Paragraph 0197; 0198
(2016/10/09)
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- One-Pot Copper(I)-Catalyzed Ligand/Base-Free Tandem Cyclooxidative Synthesis of Quinazolinones
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A novel and efficient Cu(I)-catalyzed ligand- and base-free multipathway domino strategy has been developed for the synthesis of 2-substituted quinazolinones. The reaction utilizes 2-bromobenzamide and multiform substrates such as aldehydes, alcohols, and methyl arenes for a one-pot protocol, whereas TMSN3 is used as a nitrogen source. A wide range of substrate scope, functional group tolerance, and operational simplicity are synthetically useful features.
- Upadhyaya, Kapil,Thakur, Ravi Kumar,Shukla, Sanjeev K.,Tripathi, Rama Pati
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p. 5046 - 5055
(2016/07/06)
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- FeCl3-catalyzed tandem condensation/intramolecular nucleophilic addition/C-C bond cleavage: A concise synthesis of 2-substitued quinazolinones from 2-aminobenzamides and 1,3-diketones in aqueous media
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A concise approach for the synthesis of 2-substituted quinazolinones using an iron-catalyzed tandem reaction of 2-aminobenzamides with acyclic or cyclic 1,3-diketones via condensation, intramolecular nucleophilic addition, C-C bond cleavage in an aqueous solution of poly(ethylene glycol) under oxidant-free conditions has been developed.
- Shen, Guanshuo,Zhou, Haifeng,Sui, Yuebo,Liu, Qixing,Zou, Kun
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supporting information
p. 587 - 590
(2016/01/20)
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- YB(OTF)3-catalyzed synthesis of 2-substituted 4(3H)- quinazolinones via cleavage of a carbon-carbon bond
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A general, selective, and practical one-pot synthesis of 2-substituted 4(3H)-quinazolinones by the Yb(OTf)3-catalyzed cyclo-condensation of 2-Aminobenzamides with acyclic or cyclic 1,3-diketones (β-diketones) under mild and neutral reaction conditions has been developed, which involves the highly selective cleavage of a C-C bond in 1,3-diketones by Yb(OTf)3 catalyst. For example, the Yb(OTf)3-catalyzed cyclo-condensation of 2-Aminobenzamide (1a) with 1-phenylbutane-1,3-dione (2c) gave 2-methyl-4(3H)-quinazolinone (3a) in 90% yield, together with acetophenone in 65% yield. Ring-opening cyclo-condensation of 2-Aminobenzamides (1a) with cyclic 1,3-diketones (2i and 2k-m), except for cyclopentane-1,3-dione (2j), gave 2-substitued 4(3H)-quinazolinones (3i and 3k-m) with one carbonyl group.
- Yoshimura, Tsutomu,Naito, Shun-Ichi,Yuanjun, Di,Son, Aoi,Kimura, Yu,Toshimitsu, Akio,Kondo, Teruyuki
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p. 816 - 823
(2017/04/10)
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- Acceptorless Dehydrogenative Coupling of o-Aminobenzamides with the Activation of Methanol as a C1 Source for the Construction of Quinazolinones
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A strategy for the synthesis of quinazolinones via acceptorless coupling of o-aminobenzamides with methanol has been accomplished in the presence of the metal-ligand bifunctional catalyst [Cp?Ir(2,2′-bpyO)(H2O)]. Notably, this research exhibited the potential of transition-metal-catalyzed activation of methanol as a C1 source for the construction of heterocycles.
- Li, Feng,Lu, Lei,Liu, Pengcheng
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supporting information
p. 2580 - 2583
(2016/06/15)
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- A microwave catalysis in the aqueous phase a method of preparing Quinazolinone compounds
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The invention discloses a method for preparing quinazolinone in water phase through microwave catalysis. The method comprises the step: by utilizing a water-soluble coordination compound (such as 8-hydroxyquinoline) as a catalyst, carrying out high-efficiency microwave catalysis on the reaction of 2-halogenated benzaldehyde and amidine salts in pure water phase. The invention relates to a method for preparing a quinazolinone compound, which is environment-friendly, simple and convenient to operate, safe and low-cost, and high-efficiency. Compared with the prior art, the method not only can be applicable to a great deal of functional groups, high in yield, fewer in side products, but also is simple and safe to operate, low in cost, and environment-friendly.
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Paragraph 0068
(2017/02/09)
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- A synthetic quinazoline -4 (3H)-one
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The invention provides a synthesis method of quinazolin-4(3H)-ketone heterocyclic compound. A general reaction formula is as shown in the specification, wherein R1 is a substituent group and can be H, F, NO2, alkyl or alkoxy; X is halogen and can be Cl, Br or I; R2 is H, alkyl, aryl or heteroaryl. A catalyst used in reaction is copper salt and can be cuprous iodide, cuprous chloride, cuprous oxide, cuprous acetate or the like; the used alkaline is inorganic alkaline or organic alkaline and can be sodium (potassium) hydroxide, potassium carbonate, potassium phosphate, cesium fluoride, cesium carbonate, DBU or the like. Conventional heating or microwave acceleration can be adopted in a reaction implementing process; purification is realized by using a recrystallization or column chromatographical separation means. The synthesis method is easily available in raw materials, simple in process, mild in reaction condition, wide in reaction application range and capable of synthesizing various quinazolin-4(3H)-ketone heterocyclic compounds at one step by using different substrates.
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Paragraph 0025; 0028- 0030
(2016/11/17)
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- Discovery of natural alkaloid bouchardatine as a novel inhibitor of adipogenesis/lipogenesis in 3T3-L1 adipocytes
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Bouchardatine (1), a naturally occurring β-indoloquinazoline alkaloid, was synthesized. For the first time, the lipid-lowering effect and mechanism of 1 was investigated in 3T3-L1 adipocytes. Our study showed that 1 could significantly reduce lipid accumulation without cytotoxicity and mainly inhibited early differentiation of adipocyte through proliferation inhibition and cell cycle arrested in dose-dependent manner. Furthermore, the inhibition of early differentiation was reflected by down-regulation of key regulators of adipogenesis/lipogenesis, including CCAAT enhancer binding proteins (C/EBPβ, C/EBPδ, C/EBPα), peroxisome proliferator-activated receptors γ (PPARγ) and sterol-regulatory element binding protein-1c (SREBP-1c), in both of mRNA and protein levels. Subsequently decreasing the protein levels of acetyl CoA carboxylase (ACC), fatty acid synthase (FAS), and stearyl coenzyme A desaturated enzyme 1 (SCD-1), the rate-limited metabolic enzymes of fatty acid synthesis, were also observed. Further studies revealed that 1 persistently activated adenosine 5′-monophosphate (AMP)-activated protein kinase (AMPK) during differentiation, suggesting that the AMPK may be an upstream mechanism for the effect of 1 on adipogenesis and lipogenesis. Our data suggest that 1 can be a candidate for the development of new therapeutic drugs against obesity and related metabolic disorders.
- Rao, Yong,Liu, Hong,Gao, Lin,Yu, Hong,Tan, Jia-Heng,Ou, Tian-Miao,Huang, Shi-Liang,Gu, Lian-Quan,Ye, Ji-Ming,Huang, Zhi-Shu
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p. 4719 - 4727
(2015/08/03)
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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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p. 9392 - 9400
(2015/10/12)
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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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p. 85646 - 85651
(2015/11/03)
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- A catalyst-free rapid, practical and general synthesis of 2-substituted quinazolin-4(3H)-ones leading to luotonin B and E, bouchardatine and 8-norrutaecarpine
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A remarkably rapid but microwave/ultrasound/catalyst-free method has been developed for the construction of a quinazolin-4(3H)-one ring using formamide as an efficient ammonia precursor and PEG-400 as an effective solvent. The methodology afforded various 2-substituted quinazolin-4(3H)-one derivatives in good yield via a three-component reaction of isatoic anhydride, aldehydes and formamide in air. This single methodology was extended successfully to the synthesis of several alkaloids e.g. leutonin B and E, bouchardatine and 8-norrutaecarpine.
- Rao, K. Raghavendra,Mekala, Ramamohan,Raghunadh, Akula,Meruva, Suresh Babu,Kumar, S. Praveen,Kalita, Dipak,Laxminarayana, Eppakayala,Prasad, Bagineni,Pal, Manojit
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p. 61575 - 61579
(2015/08/03)
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- The cascade synthesis of quinazolinones and quinazolines using an α-MnO2 catalyst and tert-butyl hydroperoxide (TBHP) as an oxidant
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Heterogeneously catalyzed synthesis of quinazolinones or quinazolines is reported in this study. An α-MnO2 catalyst is found to be highly active and selective in the oxidative cyclization of anthranilamides or aminobenzylamines with alcohols using TBHP as an oxidant. This protocol exhibits a broad substrate scope, and is operationally simple without an additive.
- Zhang, Zhe,Wang, Min,Zhang, Chaofeng,Zhang, Zhixin,Lu, Jianmin,Wang, Feng
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supporting information
p. 9205 - 9207
(2015/06/02)
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- Convenient synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones: Applications towards the synthesis of drugs
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Simple, convenient, and green synthetic protocols have been developed for the one pot synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones under catalyst and solvent free conditions. The multicomponent reaction (3-MCR) involving isatoic anhydride, an amine, and orthoester afforded the 2,3-disubstituted quinazolin-4(3H)-ones in excellent yields under classical heating at 120 °C for 5 h or under microwave irradiation at 140°C for 20-30 min. The use of ammonium acetate instead of the amine provides the 2-substituted quinazolin-4(3H)-ones. The reactions are compatible with various substituted isatoic anhydrides, aryl/heteroaryl/alkyl/cycloalkyl amines, and orthoesters. The strategies are extended to the one pot tandem condensation involving isatoic anhydride, an amine, orthoester, and aldehyde to afford highly functionalized (E)-3-aryl/heteroaryl-2-styrylquinazolin/(2-(heteroaryl)vinyl)quinazolin-4(3H)-ones. The applications of the methodologies are demonstrated through the synthesis of various drugs which act on the central nervous system such as methaqualone, mebroqualone, mecloqualone, piriquialone, and diproqualone.
- Kumar, Dinesh,Jadhavar, Pradeep S.,Nautiyal, Manesh,Sharma, Himanshu,Meena, Prahlad K.,Adane, Legesse,Pancholia, Sahaj,Chakraborti, Asit K.
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p. 30819 - 30825
(2015/04/22)
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- Copper-catalyzed tandem N-arylation/condensation: Synthesis of quinazolin-4(3H)-ones from 2-halobenzonitriles and amides
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A novel, straightforward and practical copper-catalyzed domino protocol for synthesis of quinazolin-4(3H)-one derivatives from commercially available 2-halobenzonitriles and amides was successfully developed.
- Chai, Hongxin,Li, Jiarong,Yang, Liupan,Lu, Hongyan,Qi, Zhang,Shi, Daxin
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p. 44811 - 44814
(2014/12/10)
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- Metal-free aerobic oxidative C-N bond cleavage of tertiary amines for the synthesis of N-heterocycles with high atom efficiency
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An efficient metal-free aerobic oxidative C-N bond cleavage of tertiary amines has been developed to construct N-heterocycles using molecular oxygen as the sole oxidant with high atom efficiency, in which all of the three alkyl groups in tertiary amines can be utilized and transformed into N-heterocycles. This journal is the Partner Organisations 2014.
- Chen, Xiuling,Chen, Tieqiao,Zhou, Yongbo,Han, Daoqing,Han, Li-Biao,Yin, Shuang-Feng
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supporting information
p. 3802 - 3807
(2014/06/09)
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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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p. 175 - 182
(2013/04/24)
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- Building heterocyclic systems with RC(OR)2+ carbocations in recyclable bronsted acidic ionic liquids: Facile synthesis of 1-substituted 1H-1,2,3,4-tetrazoles, benzazoles and other ring systems with CH(OEt)3 and EtC(OEt)3 in [EtNH 3][NO3] and [PMIM(SO3H)][OTf]
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1-Aryl/alkyl-1H-1,2,3,4-tetrazoles can conveniently be synthesized in one-pot reactions from the corresponding amines by reaction with TMSN 3 and CH(OEt)3 using the readily available, recyclable, Bronsted acidic ionic liquids [EtNH3][NO3] IL-1 and [PMIM(SO3H)][OTf] IL-2 under mild conditions in high yields. Based on comparative reactions, whereas both ILs are excellent promoters, reactions are completed with shorter reaction times and in higher yields with IL-2. Among 24 examples provided, identical products were obtained via the two ILs, except in the case of 2-aminobenzoic acid where tetrazole was formed with IL-2 and 2-ethylquinazolin-4(3H)-one was formed with IL-1. By leaving out TMS-N 3 from the reaction, the in-situ formed CH(OEt)2 + and EtC(OEt)2+ (via their corresponding orthoesters) react under sonication with o-phenylenediamine bearing various substituents, o-aminothiophenol and o-aminophenol to form a wide array of benzazoles (benzimidazole, benzothiazole and benzoxazole) and quinazolin-4(3H)-one in high yields (18 examples). The two ILs reacted differently in reaction with 2-aminobenzamide, whereas quinazolin-4(3H)one was formed with IL-2/CH(OEt)3, the "unexpected" N-ethylquinazolin-4(3H)one was isolated with IL-1/CH(OEt)3. The latter was also formed from 2-aminobenzoic acid in IL-1/CH(OEt)3. Mechanistic implications are addressed. The reported protocols enable rapid assembly of a host of heterocyclic systems in high yields with the added advantage of recycling and re-use of the ILs.
- Aridoss, Gopalakrishnan,Laali, Kenneth K.
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experimental part
p. 2827 - 2835
(2011/06/23)
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- Synthesis of quinazolin-4(3H)-one derivatives using heteropolyacids as heterogeneous and recyclable catalysts
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A highly efficient and simple procedure for the synthesis of quinazolin-4(3H)-ones from the condensation of 2-aminobenzamide with triethylorthoesters in presence of a catalytic amounts of heteropolyacids in various solvents is reported.
- Allameh,Hashemi,Heravi,Bamoharram
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experimental part
p. 1588 - 1590
(2012/01/06)
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- Amino acids as the nitrogen-containing motifs in copper-catalyzed domino synthesis of N -heterocycles
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A copper-catalyzed domino method for synthesis of quinazolinones has been developed using readily available α-amino acids as the nitrogen-containing motifs. The domino process underwent Ullmann-type N-arylation, decarboxylation, aerobic oxidation, and intramolecular addition. This method should provide a new and useful strategy for construction of N-heterocycles.
- Xu, Wei,Fu, Hua
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experimental part
p. 3846 - 3852
(2011/07/08)
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- KAl(SO4)2·12H2O (Alum) catalyzed one-pot three-component synthesis of 2-alkyl and 2-aryl-4(3H)-quinazolinone under microwave irradiation and solvent free conditions
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Twenty 2,3-disubstituted-4(3H)-quinazolinones were synthesed by one-pot three-component method with isatoic anhydride, orthoesters and amines as raw materials in the presence of KAl(SO4)2·12H 2O (Alum) under microwave irradiation and solvent-free conditions. 6-Bromo-2-propyl-3-p-tolylquinazolin-4(3H)-one (4m), 6-bromo-2-methyl-3- phenethylquinazolin-4(3H)-one (4n) and 6-bromo-2-ethyl-3-phenethylquinazolin- 4(3H)-one (4o) were characterized by IR, 1H NMR, 13C NMR and elemental analysis. Twenty 2,3-disubstituted-4(3H)-quinazolinones were synthesed by one-pot three-component method with isatoic anhydride, orthoesters and amines as raw materi-als in the presence of KAl(SO4) 2·12H2O (Alum) under microwave irradiation and solvent-free conditions. 6-Bromo-2-propyl-3-p-tolylquinazolin-4(3H)-one (4m), 6-bromo-2-methyl-3-phenethylquinazolin-4(3H)-one (4n) and 6-bromo-2-ethyl-3- phenethylquina-zolin-4(3H)-one (4o) were characterized by IR, 1H NMR, 13C NMR and elemental analysis. Copyright
- Mohammadi, Ali A.,Sadat Hossini
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experimental part
p. 1982 - 1984
(2012/06/04)
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- Identification of novel quinazolin-4(3H)-ones as inhibitors of thermolysin, the prototype of the M4 family of proteinases
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A combinatorial series of novel quinazolin-4(3H)-ones were synthesised and their structures were established based on spectroscopic data (IR, NMR, EI-MS, and FAB-MS). The compounds were tested for inhibition of the zinc metalloproteinase thermolysin (TLN) utilizing a chemical array-based approach. Some of the compounds were found to inhibit TLN, with IC50 values ranging from 0.0115 μM (compound 3) to 122,637 μM (compound 29). Compound 3 [3-phenyl-2-(trifluoromethyl) quinazolin-4(3H)-one] (IC50 = 0.0115 μM) and compound 35 [3-(isopropylideneamino)-2,2-dimethyl-2,3-dihydroquinazolin-4 (1H)-one] (IC50 = 0.2477 μM) were found to be the most potent inhibitors.
- Khan, Mahmud Tareq Hassan,Khan, Rasool,Wuxiuer, Yimingjiang,Arfan, Mohammad,Ahmed, Manzoor,Sylte, Ingebrigt
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experimental part
p. 4317 - 4327
(2010/09/12)
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- Discovery of N-(4-methoxyphenyl)-N,2-dimethylquinazolin-4-amine, a potent apoptosis inducer and efficacious anticancer agent with high blood brain barrier penetration
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As a continuation of our structure-activity relationship (SAR) studies on 4-anilinoquinazolines as potent apoptosis inducers and to identify anticancer development candidates, we explored the replacement of the 2-Cl group in our lead compound 2-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine (6b, EP128265, MPI-0441138) by other functional groups. This SAR study and lead optimization resulted in the identification of N-(4-methoxyphenyl)-N,2- dimethylquinazolin-4-amine (6h, EP128495, MPC-6827) as an anticancer clinical candidate. Compound 6h was found to be a potent apoptosis inducer with EC 50 of 2 nM in our cell-based apoptosis induction assay. It also has excellent blood brain barrier penetration, and is highly efficacious in human MX-1 breast and other mouse xenograft cancer models.
- Sirisoma, Nilantha,Pervin, Azra,Zhang, Hong,Jiang, Songchun,Willardsen, J. Adam,Anderson, Mark B.,Mather, Gary,Pleiman, Christopher M.,Kasibhatla, Shailaja,Tseng, Ben,Drewe, John,Cai, Sui Xiong
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experimental part
p. 2341 - 2351
(2010/03/31)
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- Decomposition of formamide assisted by microwaves, a tool for synthesis of nitrogen-containing heterocycles
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Generation of ammonia via thermal decomposition of formamide was studied under microwave conditions to provide an efficient tool for the synthesis of nitrogen-containing heterocycles. Quinazolin-4-ones, which are known as building blocks for molecules with pharmaceutical interest, were chosen as examples. Our work confirms that reactants may have different behaviours under microwaves, depending on power input, reached temperature and pressure in the vials. Full control and fine tuning of these parameters are achievable using modern microwave technology.
- Nouira, Ines,Kostakis, Ioannis K.,Dubouilh, Carole,Chosson, Elizabeth,Iannelli, Mauro,Besson, Thierry
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body text
p. 7033 - 7036
(2009/04/07)
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- Rapid synthesis of 2,3-disubstituted-quinazolin-4-ones enhanced by microwave-assisted decomposition of formamide
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An efficient methodology for the preparation of a series of 2,3-disubstituted-quinazolin-4(3H)-ones is described via a three step reaction from anthranilic acid. The obtained results also reveal that microwave-assisted rapid decomposition of formamide under controlled conditions of power, temperature and time is a very convenient source of ammonia for the synthesis of 2-substituted-quinazolin-4(3H)-ones and other rings.
- Kostakis, Ioannis K.,Elomri, Abdelhakim,Seguin, Elisabeth,Iannelli, Mauro,Besson, Thierry
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p. 6609 - 6613
(2008/03/12)
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