有机化学 ›› 2014, Vol. 34 ›› Issue (12): 2478-2486.DOI: 10.6023/cjoc201407025 上一篇    下一篇

研究论文

Cu催化新型苯并[e]吡唑并[1,5-c][1,3]噻嗪类化合物的合成

李明, 张建薇, 文丽荣   

  1. 青岛科技大学化学与分子工程学院 青岛 266042
  • 收稿日期:2014-07-14 修回日期:2014-08-25 出版日期:2014-12-25 发布日期:2014-09-09
  • 通讯作者: 文丽荣 E-mail:wenlirong@qust.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21072110,21372137)和山东省自然科学基金(No.ZR2012BM003)资助项目.

Cu-Catalyzed Synthesis of Novel Benzo[e]pyrazolo[1,5-c][1,3]-thiazine Derivatives

Li Ming, Zhang Jianwei, Wen Lirong   

  1. College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042
  • Received:2014-07-14 Revised:2014-08-25 Online:2014-12-25 Published:2014-09-09
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21072110, 21372137) and the Natural Science Foundation of Shandong Province (No. ZR2012BM003).

基于底物设计的概念, 建立了一种以1-(2-溴芳基)-3-乙氧基-3-(取代胺基)-2-丙烯-1-酮(1)为原料, 经由5-(2-溴芳基)-3-取代胺基-1H-吡唑(2)和异硫氰酸酯(3)在溴化亚铜/邻菲罗啉催化下高化学选择性地合成苯并[e]吡唑并[1,5-c][1,3]噻嗪类衍生物的新方法. 该方法操作简单、反应条件温和且收率高.

关键词: 苯并[e]吡唑并[1,5-c][1,3]噻嗪, 1-(2-溴芳基)-3-乙氧基-3-(取代胺基)-2-丙烯-1-酮, 5-(2-溴芳基)-3-取代胺基-1H-吡唑, 异硫氰酸酯, 铜催化, 偶联反应

Based on substrate-design concept, a high chemoselectivitive synthetic strategy of novel benzo[e]pyrazolo[1,5-c][1,3]thiazine compounds through the Cu-catalyzed reactions of 5-(2-bromoaryl)-1H-pyrazol-3-amines and isothiocyanates was developed by using 1-(2-bromoaryl)-3-ethoxy-3-amino-prop-2-en-1-ones as raw material, which has advantages of simple operation, mild reaction conditions and high yields.

Key words: benzo[e]pyrazolo[1,5-c][1,3]thiazines, 1-(2-bromoaryl)-3-ethoxy-3-amino-prop-2-en-1-ones, 5-(2-bromoaryl)-1H-pyrazol-3-amines, isothiocyanates, Cu-catalysis, coupling reaction