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


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   

  1. 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
  • 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 Haifenga, Liao Peiqiub, Diao Quanpinga, Li Tiechuna, Xin Guanga, Han Linana, Hou Dongyana   

  1. 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).

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