有机化学 ›› 2021, Vol. 41 ›› Issue (1): 318-324.DOI: 10.6023/cjoc202007003 上一篇    下一篇

研究论文

铜催化氧化和Aza-Diels-Alder反应三组分合成喹啉

秦锋a, 汤琳a, 黄飞a, 李晓悦a, 张武a,*()   

  1. a 安徽师范大学化学与材料科学学院 安徽芜湖 241000
  • 收稿日期:2020-07-01 修回日期:2020-08-07 发布日期:2020-08-31
  • 通讯作者: 张武
  • 作者简介:
    * Corresponding author. E-mail:
  • 基金资助:
    国家自然科学基金(21272006)

Copper-Catalyzed Three-Component Synthesis of Quinolines via
Oxidation and Aza-Diels-Alder Reaction

Feng Qina, Lin Tanga, Fei Huanga, Xiaoyue Lia, Wu Zhanga,*()   

  1. a College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000
  • Received:2020-07-01 Revised:2020-08-07 Published:2020-08-31
  • Contact: Wu Zhang
  • Supported by:
    the National Natural Science Foundation of China(21272006)

以苯胺、苯乙烯为原料, 二甲基亚砜(DMSO)为C1合成子, 开发了一种铜催化三组分反应合成喹啉衍生物的方法. 机理研究表明, 反应先形成亚胺中间体, 再发生Aza-Diels-Alder反应. 该方法具有高效、环境友好和底物适用范围广等特点.

关键词: 铜催化, 多组分反应, 喹啉衍生物, Aza-Diels-Alder反应

A tandem three-component reaction for the synthesis of quinolines from anilines, styrene and dimethyl sulfoxide (DMSO) has been developed. Dimethyl sulfoxide (DMSO) served as one-carbon synthon and solvent. The mechanism studies revealed that imine intermediate was involved and inverse electron demand Aza-Diels-Alder reaction was occurred. This method is featured by environmentally benign, good functional group tolerance and good to excellent yield.

Key words: copper-catalyzed, multi-component reaction, quinoline derivatives, Aza-Diels-Alder reaction