Reaction of fluorine-containing ?-ketoesters with bifunctional N-nucleophiles

Abstract

1. Fluoroalkyl β-ketoesters with phenylhydrazine at 20‡C form phenylhydrazones of the β-ketoesters, which form hydroxypyrazoles on heating. 2. 4,4-Difluoroacetoacetic ester with ethylenediamine yields the 3,3′-(N,N′-ethylenediamine)-bis-4,4-difluoro-2-butenoate ester whereas on lengthening the fluoroalkyl substituent internal salts of the aminoethylamides of the β-keto acids are formed from the β-ketoesters. 3. Hydrazine and o-phenylenediamine react with fluorine-containing β-ketoesters with the formation of pyrazoles and benzodiazepinones respectively.