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

A Kivrak, RC Larock - The Journal of organic chemistry, 2010 - ACS Publications
A Kivrak, RC Larock
The Journal of organic chemistry, 2010ACS Publications
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.
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.
ACS Publications
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