Chinese Journal of Organic Chemistry >
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).
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.
Yu Haifeng , Li Tiechun , Liao Peiqiu , Diao Quanping , Xin Guang , Hou Dongyan . Acidity-Controlled Indolylation of 3, 3-Bis(ethylthio)acrylate[J]. Chinese Journal of Organic Chemistry, 2014 , 34(5) : 956 -961 . DOI: 10.6023/cjoc201312020
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