N-碘丁二酰亚胺(NIS)催化3-取代吲哚衍生物的合成  

N-Iodosuccinimide(NIS)Promoted Synthesis of 3-Substituted Indole Derivatives

作　　者：钱存卫 韩容 沈芷欣 李倩 陈选荣 Qian Cunwei;Han Rong;Shen Zhixing;Li Qian;Chen Xuanrong(School of Chemical&Environmental Engineering,Yancheng Teachers College,Yancheng 224007;Instumental Analysis Center,Yancheng Teachers College,Yancheng,224051,Jiangsu,China)

机构地区：[1]盐城师范学院化学与环境工程学院,盐城224007 [2]盐城师范学院分析测试中心,盐城224007

出　　处：《有机化学》2022年第8期2496-2503,共8页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21801218)资助项目。

摘　　要：发展了一个以N-卤丁二酰亚胺为催化剂的吲哚与α,β-不饱和酮的迈克尔加成反应体系.首先以吲哚对查尔酮的迈克尔加成反应为模板反应,探索了该反应的优化条件.实验结果表明,该反应的优化条件是以10mol%N-碘丁二酰亚胺(NIS)为催化剂,CH_(3)CN为溶剂,在室温下搅拌反应18h,查尔酮与吲哚可以顺利反应,获得了1,3-二苯基-3-(1H-吲哚-3-基)-1-丙酮,分离收率可达90%.其次探索了该优化条件的底物适应性,实验结果显示,该优化条件可以使吲哚、1-甲基吲哚、6-甲基吲哚与查尔酮以及苯亚甲基丙酮等多种α,β-不饱和酮反应,生成目标产物,收率在51%~90%之间.该反应的条件温和,操作简单.A catalytic procedure for Michael addition reaction of indole or its derivatives withα,β-unsaturated ketones catalyzed by N-halosuccinimide has been successfully developed.Firstly,the Michael addition reaction of indole with chalcone was used as the template reaction,and the optimal conditions of the reaction were explored.The experimental results show that the optimal condition employs 10 mol%N-iodosuccinimide(NIS)as catalyst,CH_(3)CN as solvent,room temperature as reaction temperature and 18 h as reaction time.Under this optimized conditions,the reaction of chalcone and its derivatives with variousα,β-unsaturated ketone can proceed smoothly to obtain the aimed product.The yields of these reactions ranged from 51%to 90%.The reaction conditions are mild and the reaction operation is simple.

关 键 词：N-碘丁二酰亚胺(NIS) 催化 吲哚 α β-不饱和酮 迈克尔加成 

分 类 号：O626[理学—有机化学]