- Transition-metal and oxidant-free approach for the synthesis of diverse N-heterocycles by TMSCl activation of isocyanides
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A highly efficient TMSCl-mediated addition of N-nucleophiles to isocyanides has been achieved. This transition-metal and oxidant-free strategy has been applied to the construction of various N-heterocyles such as quinazolinone, benzimidazole and benzothiazole derivatives by the use of distinct amino-based binucleophiles. The notable feature of this protocol includes its mild reaction condition, broad functional group tolerance and excellent yield. This journal is
- Chen, Fen-Er,Dong, Lin,Li, Hongyan,Liu, Jinxin,Luo, Liangliang,Xiao, You-Cai,Zhou, Yuan
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p. 29257 - 29262
(2020/10/02)
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- Metal-free C-H methylation and acetylation of heteroarenes with PEG-400
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The generation of a methyl carbon source from renewable and cheap sources is challenging. Herein, we describe a novel and an efficient route for methylation and acetylation of aza-heteroarenes using PEG-400 under O2and TsOH·H2O for the first time by tuning the reaction conditions using a different set of starting materials. The key features of the current protocol are oxidative C-O and C-C bond scission under metal-free conditions with good functional group tolerance, and a broad substrate scope. The potential applicability of the designed methodology was demonstrated for the synthesis of central nervous system (CNS) depressant and anticonvulsant drug molecules by a one-pot strategy.
- Kudale, Vishal Suresh,Wang, Jeh-Jeng
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supporting information
p. 3506 - 3511
(2020/06/25)
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- Screening of natural deep eutectic solvents for green synthesis of 2-methyl-3-substituted quinazolinones and microwave-assisted synthesis of 3-aryl quinazolinones in ethanol
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In this study, two fast and efficient protocols for green synthesis of 3-substituted quinazolinones were perfomed. A synthesis of 2-methyl-3-substituted quinazolinones was performed in natural deep eutectic solvents, while 3-aryl quinazolinones were obtained by using microwave assisted synthesis. Benzoxazinone, which was used as an intermediate in the synthesis of 2-methyl-3-substituted quinazolinones, was prepared conventionally from anthranilic acid and acetic anhydride. In order to find the most appropriate synthetic path, twenty natural deep eutectic solvents were applied as a solvent in these syntheses. Choline chloride:urea (1: 2) was found to be the most efficient solvent and was further used in the synthesis of 2-methyl quinazolinone derivatives (2–12). 3-Aryl quinazolinones (13–17), on the other hand, were synthesized in one-pot microwave-assisted reaction of anthranilic acid, different amines and trimethyl orthoformate. All compounds were synthesized in good to excellent yields, characterized by LC-MS/MS spectrometry and 1H- and 13C-NMR spectroscopy.
- Komar, Mario,Konjarevi?, Anastazija,Molnar, Maja
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- TBHP as Methyl Source under Metal-Free Aerobic Conditions To Synthesize Quinazolin-4(3H)-ones and Quinazolines by Oxidative Amination of C(sp3)–H Bond
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tert-Butyl hydroperoxide (TBHP) served as the methyl source under metal-free aerobic conditions in the oxidative amination of the C(sp3)–H bond to synthesize quinazolin-4(3H)-ones and quinazolines from 2-aminobenzamides and 2-carbonyl-substituted anilines, respectively.
- Mukhopadhyay, Sushobhan,Barak, Dinesh S.,Batra, Sanjay
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p. 2784 - 2794
(2018/06/04)
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- A convenient palladium-catalyzed carbonylative synthesis of 4(3H)-quinazolinones from 2-bromoformanilides and organo nitros with Mo(CO) 6 as a multiple promoter
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A novel and convenient procedure for the synthesis of quinazolinones has been developed. Using 2-bromoformanilides and organo nitros as substrates and Mo(CO)6 as a multiple promoter, the desired products were isolated in moderate to excellent yields in the presence of a palladium catalyst. Here, Mo(CO)6 was not only a CO source, but also a nitro compound reducing reagent and a cyclization promoter. This journal is the Partner Organisations 2014.
- He, Lin,Sharif, Muhammad,Neumann, Helfried,Beller, Matthias,Wu, Xiao-Feng
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supporting information
p. 3763 - 3767
(2014/08/05)
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- Eco-friendly, solvent-free novel one-pot, three-component synthesis of quinazolinones at ambient temperature catalyzed by silica gel-supported phosphomolybdic acid
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(Chemical Presented) Silica gel supported Phosphomolybdic acid (PMA.SiO2) catalyzes efficiently the one-pot three-component coupling reaction of anthranilic acid, orthoesters, and amines at room temperature to afford 4(3H)-Quinazolinones in hig
- Sabitha, Gowravaram,Reddy, N. Mallikarjuna,Prasad, M. Nagendra,Raja,Yadav
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experimental part
p. 589 - 593
(2010/09/05)
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- A novel method for the synthesis of 4(3H)-quinazolinones
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Different metal perchlorates were screened to catalyze the three-component reaction of anthranilic acid, triethyl orthoformate and amines to afford quinazolin-4(3H)-ones in solvent-free conditions. Ni(ClO4) 2 or Zn(ClO4)s
- Jing, Xiao-Bi,Li, Zhen,Pan, Xin,Shi, Yao-Cheng
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experimental part
p. 1145 - 1149
(2009/12/08)
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- Synthesis of 3,4-dihydropyrimidine-2(1H)-thiones and quinazolin-4(3H)-ones over Yb(III)-resin catalyst under solvent-free conditions
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Ytterbium(III) reagent supported on ion exchange resin is applied to the multicomponent condensation reactions under solvent-free conditions. One-pot synthesis of a library of 3,4-dihydropyrimidine-2(1H)-thiones and quinazolin-4(3H)-ones were described. The advantages of easy separation and recyclability of the catalysts were demonstrated.
- Jiang, Zhidong,Chen, Ruifang
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p. 503 - 509
(2007/10/03)
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- Silica-supported sodium hydrogen sulfate and amberlyst-15 : Two efficient heterogeneous catalysts for single-step synthesis of 4(3H)-quinazolinones from anthranilic acid, ortho esters, and amines under solvent free conditions
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The single step synthesis of 4(3H)-quinazolinones has been carried out efficiently by coupling of the three components, anthranilic acid, ortho esters, and amines in the presence of silica-supported sodium hydrogen sulfate (NaHSO4·SiO2) or Amberlyst-15 as a heterogeneous catalyst. The reaction occurred within a few minutes under solvent free conditions to afford the products in excellent yields. One of the catalysts, Amberlyst-15 can be recovered and recycled.
- Das, Biswanath,Banerjee, Joydeep
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p. 960 - 961
(2007/10/03)
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- Yb(OTf)3-catalyzed one-pot synthesis of quinazolin-4(3H)-ones from anthranilic acid, amines and ortho esters (or formic acid) in solvent-free conditions
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An efficient synthesis of an array of quinazolin-4(3H)-ones from anthranilic acid, ortho esters (or formic acid) and amines using Yb(OTf)3 in one-pot under solvent-free conditions is described. Compared with the classical reaction conditions, this new synthetic method has the advantage of excellent yields (75-99%), shorter reaction time (few minutes) and reusability of the catalyst.
- Wang, Limin,Xia, Jianjun,Qin, Fang,Qian, Changtao,Sun, Jie
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p. 1241 - 1247
(2007/10/03)
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