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

doi:10.6023/cjoc201312020

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (5): 956-961.DOI: 10.6023/cjoc201312020 Previous Articles Next Articles

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酸度调控的3,3-二乙硫基丙烯酸酯的吲哚化反应

于海丰^a, 李铁纯^a, 廖沛球^b, 刁全平^a, 辛广^a, 侯冬岩^a

a 鞍山师范学院化学与生命科学学院鞍山 114007;
b 东北师范大学化学学院长春 130024

收稿日期:2013-12-16 修回日期:2014-01-06 发布日期:2014-01-16
通讯作者: 于海丰 E-mail:yuhf68105@sina.com
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

Yu Haifeng^a, Li Tiechun^a, Liao Peiqiu^b, Diao Quanping^a, Xin Guang^a, Hou Dongyan^a

a School of Chemistry and Life Science, Anshan Normal University, Anshan 114007;
b Department of Chemistry, Northeast Normal University, Changchun 130024

Received:2013-12-16 Revised:2014-01-06 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.

Key words: α-oxo ketene dithioacetals, 3,3-bis(ethylthio)acrylates, indole derivatives, necleophilic substitution

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Yu Haifeng, Li Tiechun, Liao Peiqiu, Diao Quanping, Xin Guang, Hou Dongyan. Acidity-Controlled Indolylation of 3, 3-Bis(ethylthio)acrylate[J]. Chin. J. Org. Chem., 2014, 34(5): 956-961.

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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

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