Selective Synthesis of 3-(3-Indolyl)-3-(methylthio)acrylate and 3-(3-Indolyl)-3-oxopropanoate

doi:10.6023/cjoc201403055

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (9): 1851-1856.DOI: 10.6023/cjoc201403055 Previous Articles Next Articles

3-吲哚基-3-甲硫基丙烯酸酯和3-吲哚基-3-氧代丙酸酯的选择性合成

于海丰^a, 廖沛球^b, 刁全平^a, 李铁纯^a, 辛广^a, 韩立楠^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:2014-03-25 修回日期:2014-04-17 发布日期:2014-05-06
通讯作者: 于海丰, 侯冬岩 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 和 2012KJ02)资助项目.

Selective Synthesis of 3-(3-Indolyl)-3-(methylthio)acrylate and 3-(3-Indolyl)-3-oxopropanoate

Yu Haifeng^a, Liao Peiqiu^b, Diao Quanping^a, Li Tiechun^a, Xin Guang^a, Han Linan^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:2014-03-25 Revised:2014-04-17 Published:2014-05-06
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20272008) and the Science Foundation of Anshan City (Nos. 2011MS44, 2012KJ02).

1. Selective Synthesis of 3-(3-Indolyl)-3-(methylthio)acrylate and 3-(3-Indolyl)-3-oxopropanoate.PDF(598KB)

Abstract

The indolylation reaction of 3,3-bis(methylthio)acrylates was performed at 10 ℃ when the molar ratio of 3,3-bis(methylthio)acrylates, indoles and trifluoroacetic acid (TFA) was 1:1:15. It showed that 3-(3-indolyl)-3-(methyl- thio)acrylate and 3-(3-indolyl)-3-oxopropanoate could be selectively obtained in excellent yield by controlling the detention time of 3-(3-indolyl)-3-(methylthio)acrylate in the silica gel. This transformation is characterized by mild reaction conditions, simple procedure, good yield, and perfect selectivity.

Key words: α-oxo ketene dithioacetal, 3,3-bis(methylthio)acrylate, 3-(3-indolyl)-3-oxopropanoate, indole derivative, selective synthesis

Cite this article

Yu Haifeng, Liao Peiqiu, Diao Quanping, Li Tiechun, Xin Guang, Han Linan, Hou Dongyan. Selective Synthesis of 3-(3-Indolyl)-3-(methylthio)acrylate and 3-(3-Indolyl)-3-oxopropanoate[J]. Chin. J. Org. Chem., 2014, 34(9): 1851-1856.

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3-吲哚基-3-甲硫基丙烯酸酯和3-吲哚基-3-氧代丙酸酯的选择性合成

Selective Synthesis of 3-(3-Indolyl)-3-(methylthio)acrylate and 3-(3-Indolyl)-3-oxopropanoate

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