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Synthesis of Indazoles by the [3+2] Cycloaddition of Diazo Compounds with Arynes and Subsequent Acyl Migration

Zhijian Liu, Feng Shi, Pablo D. G. Martinez, Cristiano Raminelli and Richard C. Larock*

*Department of Chemistry, Georgetown University, Washington, D.C. 20057, Email: cw27georgetown.edu

Z. Liu, F. Shi, P. D. G. Martinze, C. Raminelli, R. C. Larock, J. Org. Chem., 2008, 73, 219-226.

DOI: 10.1021/jo702062n (free Supporting Information)



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Abstract

The [3+2] cycloaddition of a variety of diazo compounds with o-(trimethylsilyl)aryl triflates in the presence of CsF or TBAF at room temperature provides a very direct, efficient approach to a wide range of potentially biologically and pharmaceutically interesting substituted indazoles in good to excellent yields under mild reaction conditions.

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Key Words

Indazoles, Huisgen Cycloaddition


ID: J42-Y2008-0050