Indolizines. Part VI. Ring-opening reactions of 3-amino- and 3-nitrosox-indolizines

Abstract

Catalytic hydrogenation of 3-nitrosoindolizines has been shown to yield cis-3-(2-pyridyl)-acrylonitriles and -propionitriles in addition to 3-aminoindolizines. A number of syntheses of the acrylonitriles both from 3-nitroso-indolizines under reductive conditions, and from 3-aminoindolizines under oxidative conditions, have been accomplished and the nature of the intermediates in these reactions is discussed. Hydrolysis of 3-aminoindolizines with hydrochloric acid is shown to yield 3-(2-pyridyl)propionic acids.