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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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