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Simple Conversion of Enamines to 2H-Azirines and Their Rearrangements under Thermal Conditions

Xiaoxun Li, Yunfei Du*, Zhidan Liang, Xiangke Li, Yan Pan and Kang Zhao

*Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China, Email:

X. Li, Y. Du, Z. Liang, X. Li, Y. Pan, K. Zhao, Org. Lett., 2009, 11, 2643-2646.

DOI: 10.1021/ol9006663

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Various substituted enamine derivatives can be conveniently converted to the corresponding 2H-azirines mediated by phenyliodine (III) diacetate (PIDA). The formed 2-aryl-2H-azirines allow the synthesis of indole-3-carbonitriles or isoxazoles via thermal rearrangements.

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Key Words

2H-azirines, phenyliodine (III) diacetate, indoles

ID: J54-Y2009-1820