The Journal of organic chemistry

Synthesis of Dihydrobenzisoxazoles by the [3+ 2] Cycloaddition of Arynes and Oxaziridines

A Kivrak, RC Larock

Index: Kivrak, Arif; Larock, Richard C. Journal of Organic Chemistry, 2010 , vol. 75, # 21 p. 7381 - 7387

Full Text: HTML

Citation Number: 32

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 ...