酸度调控的3,3-二乙硫基丙烯酸酯的吲哚化反应
收稿日期: 2013-12-16
修回日期: 2014-01-06
网络出版日期: 2014-01-16
基金资助
国家自然科学基金（No. 20272008）和鞍山市科技基金（Nos. 2011MS44，2012KJ02）资助项目.
Acidity-Controlled Indolylation of 3, 3-Bis(ethylthio)acrylate
Received date: 2013-12-16
Revised date: 2014-01-06
Online published: 2014-01-16
Supported by
Project supported by the National Natural Science Foundations of China (No. 20272008) and the Science Foundation of Anshan City (Nos. 2011MS44, 2012KJ02).
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.
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
于海丰 , 李铁纯 , 廖沛球 , 刁全平 , 辛广 , 侯冬岩 . 酸度调控的3,3-二乙硫基丙烯酸酯的吲哚化反应[J]. 有机化学, 2014 , 34(5) : 956 -961 . DOI: 10.6023/cjoc201312020
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.
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