有机化学 ›› 2014, Vol. 34 ›› Issue (8): 1639-1645.DOI: 10.6023/cjoc201402036 上一篇    下一篇

研究论文

AlCl3催化活化sp3-C—H键合成3-氮杂芳基-3-羟基-2-羟吲哚

翟娇娇, 姚志刚, 徐凡   

  1. 苏州大学材料与化学化工学部 苏州 215123
  • 收稿日期:2014-02-28 修回日期:2014-04-07 出版日期:2014-08-25 发布日期:2014-04-16
  • 通讯作者: 徐凡 E-mail:xufan@suda.edu.cn
  • 基金资助:
    国家自然科学基金(Nos.21272168,20872106)资助项目.

Efficient Synthesis of 3-Azaarene-substituted 3-Hydroxy-2-oxindoles via Aluminium Chloride Catalyzed sp3-C—H Functionalization

Zhai Jiaojiao, Yao Zhigang, Xu Fan   

  1. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123
  • Received:2014-02-28 Revised:2014-04-07 Online:2014-08-25 Published:2014-04-16
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21272168, 20872106).

3-氮杂芳基-3-羟基-2-羟吲哚化合物的合成方法近年来吸引了化学家的关注. 本工作以经典Lewis酸AlCl3催化2-甲基吡啶化合物与靛红的加成反应,高效合成了3位氮杂芳基取代的3-羟基-2-羟吲哚化合物. 与已有报道相比,该方法所用催化剂简单、易得、价廉,且催化剂用量较小,反应收率高. 同时,我们根据原位核磁的结果对该反应的机理进行了推测.

关键词: 3-羟基-2-羟吲哚, 三氯化铝, 催化, C—H键活化

The synthesis of 3-azaarene-substituted 3-hydroxy-2-oxindoles has been receiving considerable attention in recent years. This paper describes an efficient method for the synthesis of 3-azaarene-substituted 3-hydroxy-2-oxindoles by aluminium chloride catalyzed reaction of 2-methylpyridines with isatins, which provides a practical and atom-economical process to afford this type of biologically important compounds in good yields using commercially available and inexpensive catalyst. A mechanism involving an aluminium chloride-catalyzed sp3-C—H activation is proposed and the evidence of that is provided by in situ 1H NMR.

Key words: 3-hydroxy-2-oxindole, aluminium chloride, catalysis, C—H bond activation