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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, Iowa State University, Ames, Iowa 50010, Email: larockiastate.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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Synthesis of 3-Substituted Indazoles from Arynes and N-Tosylhydrazones

P. Li, J. Zhao, C. Wu, R. C. Larock, F. Shi, Org. Lett., 2011, 13, 3340-3343.

Synthesis of 2H-Indazoles by the [3 + 2] Cycloaddition of Arynes and Sydnones

C. Wu, Y. Fang, R. C. Larock, F. Shi, Org. Lett., 2010, 12, 2171-2173.


Key Words

Indazoles, Huisgen Cycloaddition


ID: J42-Y2008-0050