One-pot synthesis of benzothiazolones from 2-haloanilines, potassium sulfide and N,N-dimethylformamide
首发时间:2015-07-16
Abstract:Benzothiazolones represent an important class of compounds found in medicines and pesticides. The traditional synthetic methods to prepare of benzothiazolones usually suffered from the limitation of commercially available starting materials such as substituted o-aminothiophenols, toxic carbonyl sources or multiple steps. In this paper, an efficient Cu-catalyzed one-pot synthesis of benzothiazolones directly from easily available 2-haloanilines, potassium sulfide and N,N-dimethylformamide (DMF) as strating materials has been developed. In this protocol, C-S and C-N bond formation occurs during reactions with yields up to 87% after optimization of reaction conditions, which was CuSO4 (10 mol%), 2,2'-bipyridine (10 mol%), and NaOH (3 equiv) at 120 C for 18 h without inert atmosphere. Electron-donating groups seemed to be beneficial to the catalysis than electron-withdrawing groups, which indicated the electron-donating groups would benefit the nucleophilic attack during reaction. The mechanism studies revealed that the carbonyl group of product came from DMF.
keywords: Organic Chemistry Benzothiazolones Copper Catalysis N,N-Dimethylformamide
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一锅法三组分合成苯并噻唑酮
摘要:苯并噻唑酮是一类重要的化合物,通常可用于农药和杀虫剂。传统的苯并噻唑酮合成方法通常受限于难以得到的取代邻胺基噻吩,具有毒性的一氧化碳或需要多步反应。本文采用易得的2-卤苯胺、硫化钾和DMF为原料,三组分一锅法合成苯并噻唑酮。该反应中,C-S和C-N键的形成可一次完成,通过反应条件的筛选,without inert atmosphere. 最优条件是:CuSO4 (10 mol%), 2,2'-联吡啶 (10 mol%), NaOH (3 equiv),反应温度为120 C,反应时间18小时,最高收率可达到87%。推电子基团较吸电子基团更有利于反应,说明推电子基团在反应中有助于亲核进攻反应。反应机理的研究表明产物中的羰基来源于DMF。
关键词: 有机化学 苯并噻唑 铜 催化 N,N'-二甲基甲酰胺
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No.4649429936421435****
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