Synthesis of indazoles by the [3+ 2] cycloaddition of diazo compounds with arynes and subsequent acyl migration

Z Liu, F Shi, PDG Martinez, C Raminelli…

Index: Liu, Zhijian; Shi, Feng; Martinez, Pablo D. G.; Raminelli, Cristiano; Larock, Richard C. Journal of Organic Chemistry, 2008 , vol. 73, # 1 p. 219 - 226

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Citation Number: 133

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. Simple diazomethane derivatives afford N-unsubstituted indazoles or 1-arylated indazoles, depending upon the ...