有机化学 ›› 2014, Vol. 34 ›› Issue (5): 956-961.DOI: 10.6023/cjoc201312020 上一篇    下一篇

研究论文

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   

  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:2013-12-16 修回日期:2014-01-06 出版日期:2014-05-25 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 Haifenga, Li Tiechuna, Liao Peiqiub, Diao Quanpinga, Xin Guanga, 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:2013-12-16 Revised:2014-01-06 Online:2014-05-25 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

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