AlCl3催化活化sp3-C—H键合成3-氮杂芳基-3-羟基-2-羟吲哚有机化学.pdfVIP

DOI: 10.6023/cjoc201402036 研究论文 有机化学 Chinese Journal of Organic Chemistry ARTICLE 3 AlCl 催化活化sp -C—H 键合成3-氮杂芳基-3-羟基-2-羟吲哚 3 翟娇娇 姚志刚 徐 凡* (苏州大学材料与化学化工学部 苏州 215123) 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 Efficient Synthesis of 3-Azaarene-substituted 3-Hydroxy-2-oxindoles 3 via Aluminium Chloride Catalyzed sp -C—H Functionalization Zhai, Jiaojiao Yao, Zhigang Xu, Fan* (College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123) 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 alumin- ium 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 3 mechanism involving an aluminium chloride-catalyzed sp -C—H activation is proposed and the evidence of that is provided by in situ 1H NMR. Keywords 3-hydroxy-2-oxindole; aluminium chloride; catalysis; C—H bond activation 3