铜(I)催化邻炔基芳基异硫氰酸酯与(E)-2-(苄基氨基)乙酸酯串联双环化反应快速合成5H-苯并咪唑[5,1-b][1,3]噻嗪  

A Rapid Synthesis of 5H-Benzo[d]imidazo[5,1-b][1,3]thiazines via Copper(I)-Catalyzed Cascade Bicyclization of o-Alkynylphenyl Isothiocyanates with Ethyl(E)-2-(Benzylideneamino)acetates

作　　者：张亚辉 吴文锦 张可心 黎双双 郝文燕[1] Zhang Yahui;Wu Wenjin;Zhang Kexin;Li Shuangshuang;Hao Wenyan(Key Laboratory of Functional Small Organic Molecules of Ministry of Education,Jiangxi Key Laboratory of Green Chemistry,College of Chemistry&Chemical Engineering,Jiangxi Normal University,Nanchang 330022)

机构地区：[1]江西师范大学化学与化工学院功能有机小分子教育部重点实验室江西省绿色化学重点实验室,南昌330022

出　　处：《有机化学》2021年第5期1982-1990,共9页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.21762023,22061021);江西省自然科学基金(No.2018BAB203006)资助项目.

摘　　要：以廉价的铜盐作为催化剂,快速高效地实现了邻炔基芳基异硫氰酸酯与(E)-2-(苄基氨基)乙酸酯的串联双环化反应,以中等至良好产率合成了一系列5H-苯并[d]咪唑[5,1-b][1,3]噻嗪类化合物.该反应操作简单,利用一步[3+2]环加成继而分子内亲核加成串联机制,一锅法高效构建了两个新环.A rapid and efficient protocol for copper(I)-catalyzed tandem bicyclization of o-alkynylphenyl isothiocyanates with ethyl(E)-2-(benzylideneamino)acetates has been developed,affording a series of 5H-benzo[d]imidazo[5,1-b][1,3]thiazines in moderate to good yields.In this transformation,a[3+2]cycloaddition reaction mechanism was involved and two new rings were formed in one pot.

关 键 词：铜催化 串联双环化 5H-苯并咪唑[5 1-b][1 3]噻嗪 

分 类 号：O626[理学—有机化学]