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One-Pot Synthesis of N-Alkyl Benzotriazoles via a Brønsted Acid-Catalyzed Three-Component Reaction
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2017-11-09 12:40:34 , DOI: 10.1002/adsc.201700873 Xiangdong Wang 1 , Chunqi Jia 1 , Yadong Feng 1 , Lianhui Wang 1 , Xiuling Cui 1
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2017-11-09 12:40:34 , DOI: 10.1002/adsc.201700873 Xiangdong Wang 1 , Chunqi Jia 1 , Yadong Feng 1 , Lianhui Wang 1 , Xiuling Cui 1
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A novel three-component condensation reaction of benzotriazoles, aldehydes and tertiary anilines efficiently catalyzed by readily available organic acid p-toluenesulfonic acid (PTSA) has been developed. A series of N-alkyl benzotriazoles were synthesized in up to 97% yield for 21 examples starting from anilines, benzotriazoles and formaldehyde. This strategy features a simple system, atom economy, environmental friendliness, high efficiency, excellent regioselectivity, good functional group tolerance, easily available starting materials, and cheap catalyst. The mechanistic studies indicated that aza quinone methide was probably involved as an intermediate in this transformation.
中文翻译：
布朗斯台德酸催化三组分反应一锅法合成N-烷基苯并三唑
已经开发出一种新型的三组分苯并三唑，醛和叔苯胺的缩合反应，该反应由容易获得的有机酸对甲苯磺酸（PTSA）有效地催化。从苯胺，苯并三唑和甲醛开始，对于21个实例，以高达97％的产率合成了一系列N-烷基苯并三唑。该策略的特点是系统简单，原子经济，环境友好，效率高，区域选择性好，官能团耐受性好，原料易得，催化剂便宜。机理研究表明，氮杂苯醌甲基化物可能作为这种转化的中间体。
更新日期：2017-11-09
中文翻译：
布朗斯台德酸催化三组分反应一锅法合成N-烷基苯并三唑
已经开发出一种新型的三组分苯并三唑，醛和叔苯胺的缩合反应，该反应由容易获得的有机酸对甲苯磺酸（PTSA）有效地催化。从苯胺，苯并三唑和甲醛开始，对于21个实例，以高达97％的产率合成了一系列N-烷基苯并三唑。该策略的特点是系统简单，原子经济，环境友好，效率高，区域选择性好，官能团耐受性好，原料易得，催化剂便宜。机理研究表明，氮杂苯醌甲基化物可能作为这种转化的中间体。
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