Synthesis of dihydrobenzisoxazoles by the [3 + 2] cycloaddition of arynes and oxaziridines |
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Authors: | Kivrak Arif Larock Richard C |
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Institution: | Department of Chemistry, Iowa State University, Ames, Iowa 50011, United States. |
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Abstract: | Dihydrobenzisoxazoles are readily prepared in good yields by the 3 + 2] cycloaddition of oxaziridines and arynes. The reaction involves an unusual cleavage of the C-O bond of the oxaziridine and tolerates a variety of substituents on the oxaziridine and the o-(trimethylsilyl)aryl triflate to form aryl-, heteroaryl-, alkyl-, and naphthyl-substituted dihydrobenzisoxazoles. The resulting halogen-substituted dihydrobenzisoxazoles are readily elaborated to more complex products using palladium-catalyzed crossing-coupling processes. |
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