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2014 , Vol. 34 >Issue 8: 1639 - 1645

DOI: https://doi.org/10.6023/cjoc201402036

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
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  • 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

  网络出版日期: 2014-04-16

基金资助

国家自然科学基金（Nos.21272168，20872106）资助项目.

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

  • Zhai Jiaojiao ,
  • Yao Zhigang ,
  • Xu Fan
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  • College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123

Received date: 2014-02-28

  Revised date: 2014-04-07

  Online published: 2014-04-16

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21272168, 20872106).

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摘要

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

本文引用格式

翟娇娇 , 姚志刚 , 徐凡 . AlCl3催化活化sp3-C—H键合成3-氮杂芳基-3-羟基-2-羟吲哚[J]. 有机化学, 2014 , 34(8) : 1639 -1645 . DOI: 10.6023/cjoc201402036

Abstract

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

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