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

doi:10.6023/cjoc201402036

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (8): 1639-1645.DOI: 10.6023/cjoc201402036 Previous Articles Next Articles

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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

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 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

College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123

Received:2014-02-28 Revised:2014-04-07 Published:2014-04-16
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21272168, 20872106).

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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Zhai Jiaojiao, Yao Zhigang, Xu Fan. Efficient Synthesis of 3-Azaarene-substituted 3-Hydroxy-2-oxindoles via Aluminium Chloride Catalyzed sp³-C—H Functionalization[J]. Chin. J. Org. Chem., 2014, 34(8): 1639-1645.

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AlCl₃催化活化sp³-C—H键合成3-氮杂芳基-3-羟基-2-羟吲哚

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

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AlCl3催化活化sp3-C—H键合成3-氮杂芳基-3-羟基-2-羟吲哚