摘要
苯并咪唑稠合二氢苯并唑是一类复杂的氮氧杂环,在生物医药和功能性材料中具有较高的应用价值.本文在空气氛围中以苯并咪唑和2-溴苯酚为原料、廉价Cu(Ⅱ)为催化剂,采用"一锅法"合成了苯并咪唑稠合二氢苯并唑类化合物,反应经历了N-芳基化、sp^2 C-H活化、C-O环化的串联过程.研究表明,该反应对于苯并咪唑类衍生物,以及其他反应底物(如2-碘苯酚和2-羟基苯硼酸)均具有一定的官能团耐受性.本文为高效合成苯并咪唑稠合二氢苯并唑类化合物提供了一种简便方法.
Benzimidazole-fused dihydrobenzoxazoles are an important class of complex heterocycles containing both nitrogen and oxygen as building blocks for materials and pharmaceuticals. Traditional synthetic method for the skeleton lacks of step economy. This article describes the tandem cyclization of 1 H-benzimidazole and 2-bromophenol catalyzed by copper（Ⅱ） via N-arylation/sp^2 C-H activation/C-O bond cyclization to construct benzimidazole-fused dihydrobenzoxazoles in one-pot. The reaction was carried out under an air atmosphere with simple reactive conditions and easy handling. In addition, other benzimidazole derivatives, as well as 2-iodophenol and 2-hydroxybenzeneboronic acid, are also suitable for this reaction. This transformation provides a convenient method to synthesize a series of benzimidazole-fused dihydrobenzoxazoles.
作者
谢丹
赖婷婷
吴云彬
周成合
蔡桂鑫
Dan Xie Ting-Ting Lai Yun-Bin Wu Cheng-He Zhou Gui-Xin Cai(Institute ofBioorganic ＆ Medicinal Chemistry, Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China Beijing National Laboratory for Molecular Sciences, Beijing 100190, China)
出处
《中国科学：化学》
CAS
CSCD
北大核心
2017年第10期1198-1207,共10页
SCIENTIA SINICA Chimica
基金
国家自然科学基金(编号:21372186
21672173)
西南大学博士基金(编号:SWU111075)
北京分子科学国家实验室基金(编号:20140130)
中央高校基本科研业务费专项资金(编号:XDJK2017B015)资助项目
关键词
苯并咪唑
苯并唑
铜催化
串联C-H活化
C-O环化
benzimidazole, benzoxazole, copper catalyst, tandem C-H activation, C-O cyclization
