Synthesis of indazoles by the [3+2] cycloaddition of diazo compounds with arynes and subsequent acyl migration |
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Authors: | Liu Zhijian Shi Feng Martinez Pablo D G Raminelli Cristiano Larock Richard C |
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Institution: | Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA. |
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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. Simple diazomethane derivatives afford N-unsubstituted indazoles or 1-arylated indazoles, depending upon the stoichiometry of the reagents and the reaction conditions, while dicarbonyl-containing diazo compounds undergo carbonyl migration to afford 1-acyl or 1-alkoxycarbonyl indazoles selectively. |
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