摘要
通过Barbier-Grignard型反应,在Ta_2O_5催化下,2,3-二氰基对苯二酚与溴苯和Mg在四氢呋喃中一锅反应成功制备出含氮杂环化合物1,3-二芳基或烷基-2H-异吲哚-4,7-二酮,该方法新颖、方便且高效,适用于不同芳基和烷基溴代物,最高收率达到96%.此外在一些实验结果的基础上,提出了涉及亲核加成和电子转移的可能的反应机理,利用1,3-二苯基-2H-异吲哚-4,7-二酮(3a)中的醌结构与胺偶联得到了更复杂的结构.
A novel, convenient and efficient protocol to N-heterocyclic derivatives of 1,3-diaryl or diaklyl-2 H-isoindole-4,7-dione has been developed via the Barbier-Grignard-type reaction. Good to excellent yields up to 96% have been achieved by performing the reaction in one pot using Ta_2O_5 as the catalyst. The protocol displays good tolerance to different aryl and alkyl bromides. Based on some experimental results, a plausible mechanism involving nucleophilic addition and electron transfer has been proposed. The quinone structure in 1,3-diphenyl-2 H-isoindole-4,7-dione（3a） makes it coupling with amine to form more complicated structure.
作者
刘宏
董慧茹
安锐
唐渝
许开天
张渊明
Liu Hong;Dong Huiru;An Rui;Tang Yu;Xu Kaitian;Zhang Yuanming(Department of Chemistry,College of Chemistry and Materials Science,Jinan University,Guangzhou 510632)
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2018年第8期2008-2016,共9页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(No.21274083)
全国大学生创新创业培养计划(No.82617055)资助项目~~
