酸度调控的3,3-二乙硫基丙烯酸酯的吲哚化反应  

Acidity-Controlled Indolylation of 3,3-Bis(ethylthio)acrylate

作　　者：于海丰[1] 李铁纯[1] 廖沛球[2] 刁全平[1] 辛广[1] 侯冬岩[1] 

机构地区：[1]鞍山师范学院化学与生命科学学院,鞍山114007 [2]东北师范大学化学学院,长春130024

出　　处：《有机化学》2014年第5期956-961,共6页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.20272008);鞍山市科技基金(Nos.2011MS44;2012KJ02)资助项目~~

摘　　要：探讨了酸度调控的3,3-二乙硫基丙烯酸酯的吲哚化反应,选择性地合成3,3-二吲哚基丙烯酸酯和3-吲哚基-3-氧代丙酸酯.研究表明,3,3-二乙硫基丙烯酸酯与吲哚反应时,在稀酸条件下,高产率生成3,3-二吲哚基丙烯酸酯,而在浓酸条件下,生成的3-吲哚基-3-乙硫基丙烯酸酯不稳定,在后处理和柱层析分离时易水解,高产率得到3-吲哚基-3-氧代丙酸酯.The acidity controlled indolylation reaction of 3,3-bis（ethylthio）acrylates to selectively yield 3,3-di（indol-3-yl）acrylates and 3-（indol-3-yl）-3-oxopropanoates was studied. It showed that 3,3-di（indol-3-yl）acrylates were obtained in good yield under diluted acidity condition when 3,3-bis（ethylthio）acrylates reacted with indole derivatives, while the reaction performed under concentrated acidity produced 3-ethylthio-3-（indol-3-yl）acrylate, which were easily hydrolyzed to supply 3-（indol-3-yl）-3-oxopropanoates in good yield under acid condition.

关 键 词：Α-羰基二硫缩烯酮 3 3-二乙硫基丙烯酸酯 吲哚衍生物 亲核取代反应 

分 类 号：O626[理学—有机化学]