Journal article

Nitrones and oxaziridines. xx: Intramolecular nitrone 1, 3-dipolar cycloaddition by substituent interaction: Synthesis and reduction of some tetrahydropyrroloisoxazoles

DC Black, RF Crozier, ID Rae

Australian Journal of Chemistry | Published : 1978

Abstract

The reactions of C-benzoylnitrones with allylamine afford tetrahydro-5H-pyrrolo[3,4-c]isoxazoles resulting from imine formation and intramolecular 1,3-dipolar cycloadditions. Cycloaddition reactions of the same nitrones with 2-vinylpyridine and N-phenylallylamine afford 5-substituted isoxazolidines in the normal way. Reduction of the imine bond in the tetrahydropyrroloisoxazoles can be achieved by catalytic hydrogenation or sodium borohydride, and, in the case of an N-phenyl derivative, N-O bond cleavage also occurs.

University of Melbourne Researchers

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