Preparation of 3-Diazoindolin-2-imines via Cascade Reaction between Indoles and Sulfonylazides and Their Extensions to 2,3-Diaminoindoles and Imidazo[4,5-b]indoles

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• 作者：Guorong Sheng ; Kai Huang ; Zhihao Chi ; Hualong Ding ; Yanpeng Xing ; Ping Lu ; Yanguang Wang
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：October 3, 2014
• 年：2014
• 卷：16
• 期：19
• 页码：5096-5099
• 全文大小：389K
• ISSN：1523-7052

文摘

3-Diazoindolin-2-imines were constructed from indoles and sulfonylazides via an electronically matched 1,3-dipolar cycloaddition and a subsequent dehydroaromatization/ring-opening cascade. The reaction between 3-substituted indoles and sulfonyl azides provided 2-aminoindoles, while 2-substituted indoles furnished 3-aminoindoles. Moreover, 2,3-diaminoindoles could be prepared from the resulting 3-diazoindolin-2-imines and secondary amines via a rhodium-catalyzed amination. Further extension of 2,3-diaminoindoles led to the formation of imidazo[4,5-b]indoles.