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A Tandem Approach to Isoquinolines from 2-Azido-3-arylacrylates and α-Diazocarbonyl Compounds

Yun-Yun Yang, Wang-Ge Shou, Zheng-Bo Chen, Deng Hong and Yan-Guang Wang*

*Department of Chemistry, Zhejiang University, Hangzhou 310027, China, Email: orgwygzju.edu.cn

Y.-Y. Yang, W.-G. Shou, Z.-B. Chen, D. Hong, Y.-G. Wang, J. Org. Chem., 2008, 73, 3928-3930.

DOI: 10.1021/jo8003259 (free Supporting Information)


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Abstract

Readily available 2-azido-3-arylacrylates react with α-diazocarbonyl compounds and triphenylphosphine to furnish isoquinolines in good yields. The efficient and general procedure involves a Wolff rearrangement, an aza-Wittig reaction, and an electrocyclic ring closure.

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proposed reaction pathway



Key Words

Isoquinolines, Staudinger Reaction, Wittig Reaction, Wolff Rearrangement


ID: J42-Y2008-1300