有机化学 ›› 2016, Vol. 36 ›› Issue (7): 1643-1652.DOI: 10.6023/cjoc201512021 上一篇    下一篇

研究论文

温和条件下[2-氨基-3-(苯并噻唑-2-基)-4H-色烯-4-基]膦酸酯衍生物的简便合成

颜浩浩, 赵博良, 高钰, 杜大明   

  1. 北京理工大学化工与环境学院 北京 100081
  • 收稿日期:2015-12-15 修回日期:2016-01-22 发布日期:2016-03-11
  • 通讯作者: 杜大明 E-mail:dudm@bit.edu.cn
  • 基金资助:

    国家自然科学基金(No.21272024)资助项目.

Facile Synthesis of (2-Amino-3-(benzothiazol-2-yl)-4H-chromen- 4-yl)phosphonate Derivatives under Mild Conditions

Yan Haohao, Zhao Boliang, Gao Yu, Du Daming   

  1. School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081
  • Received:2015-12-15 Revised:2016-01-22 Published:2016-03-11
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21272024).

含有不同取代基的(E)-2-(苯并噻唑-2-基)-3-(2-羟基苯基)丙烯腈与亚磷酸二苯酯在水中,无催化剂催化即可发生Michael加环/环化串联反应,可以高产率地生成相应的[2-氨基-3-(苯并噻唑-2-基)-4H-色烯-4-基]膦酸酯衍生物. 同时,也尝试了水杨醛、2-(苯并噻唑-2-基)乙腈和亚磷酸二苯酯在Et3N催化下的三组分一锅法反应合成相应的膦酸酯衍生物.

关键词: Michael加成, 环化反应, 膦酸酯, 色烯, 杂环化合物

A series of (2-amino-3-(benzothiazol-2-yl)-4H-chromen-4-yl)phosphonate derivatives were synthesized in good to excellent yields by Michael addition/cyclization of diphenyl phosphite to diverse substituted(E)-2-(benzothiazol-2-yl)-3-(2-hydroxyphenyl)acrylonitriles under catalyst-free condition in water. Meanwhile, one-pot three component reaction of salicylaldehyde, 2-(benzothiazol-2-yl)acetonitrile and diphenyl phosphate was also tested using Et3N as catalyst to synthesize these phosphonate derivatives

Key words: Michael addition, cyclization, phosphonate, chromene, heterocycle