高等学校化学学报 ›› 2021, Vol. 42 ›› Issue (9): 2798.doi: 10.7503/cjcu20210260

• 有机化学 • 上一篇    下一篇

基于钯铜催化合成靛红类化合物的新方法

郭阳1,2, 林凯2, 谢凯强2, 刘晟1,2()   

  1. 1.贵州医科大学省部共建药用植物功效与利用国家重点实验室
    2.贵州省中国科学院天然产物化学重点实验室, 贵阳 550014
  • 收稿日期:2021-04-19 出版日期:2021-09-10 发布日期:2021-09-08
  • 通讯作者: 刘晟 E-mail:lsheng@126.com
  • 基金资助:
    国家自然科学基金(21762014)

Novel Approach to Isatins via Pd-Cu Catalyzed Oxidative Transformation

GUO Yang1,2, LIN Kai2, XIE Kaiqiang2, LIU Sheng1,2()   

  1. 1.State Key Laboratory of Functions and Applications of Medicinal Plants,Guizhou Medical University
    2.Key Laboratory of Chemistry for Natural Products of Guizhou Province,Chinese Academy of Sciences,Guiyang 550014,China
  • Received:2021-04-19 Online:2021-09-10 Published:2021-09-08
  • Contact: LIU Sheng E-mail:lsheng@126.com
  • Supported by:
    the National Natural Science Foundation of China(21762014)

摘要:

发展了一种合成靛红的新方法, 并进行了底物扩展, 得到了一系列靛红类化合物. 以N-烷基取代的丙烯酰苯胺类化合物为原料, 在醋酸钯、 碘化亚铜和氧气的催化及参与下, 以42%~87%的产率合成了N-烷基化的靛红衍生物. 利用该方法制备了23个靛红类化合物, 并提出了可能的反应机理. 该合成路线减少了保护基的使用, 简洁高效.

关键词: 靛红, 钯催化, 氧化, 分子内关环

Abstract:

A new method of synthesizing isatin was developed and applied to the substrate extension to get a series of isatin compounds. Using N-alkyl substituted acrylanilide compounds as raw materials, in palladium acetate, cuprous iodide and under the catalysis and participation of oxygen, N-alkylated isatin derivatives could be synthesized with the yields of 42%—87%. Using this method, 23 isatin compounds were prepared and the possible reaction mechanism was proposed. This synthetic route reduces the use of protecting groups and is simple and efficient.

Key words: Isatin, Pd-catalyzed, Oxidation, Intramolecular cyclization

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