Synthesis of Methyl (Hetarylalkyl) N-Allyl-N-phenylcarbamates and Their Transformation into 4,5-Dihydroisoxazole Derivatives

Abstract

Alkylation of aromatic carbamates with allyl bromide under liquid-liquid phase transfer catalysis furnished the corresponding N-allyl derivatives of aryl carbamates in 63–71% yields. It was found that the cycloaddition of arene carbonitrile N-oxides, generated in situ from the corresponding oximes in the presence of chloramine T, to the allyl fragment upon boiling in ethanol led to the production of the corresponding 4,5-dihydroisoxazole derivatives in 89–96% yields.