Action of Grignard reagents on N-Alkylidene- and N-Arylmethylene-aminophthalimides

Abstract

N-Alkylidene- and N-arylmethylene-aminophthalimides react with organomagnesium halides to give different products depending upon the nature of the Grignard reagent. Thus the reaction may proceed by addition of two moles of the reagent to give (2) or (3) or it may proceed through addition and cleavage of the molecule to give phthalazin-1-ones (5). These phthalazin-1-ones can also be obtained in much better yields by the action of Grignard reagents on N- aminophthalimide. Structures are based on infrared and ultraviolet spectra and the synthesis of authentic samples in some cases.