Enamidines. Part 1. Synthesis of enamidines and dihydrntriazines by the reaction of organolithium and organomagnesium compounds with aromatic nitrites

Abstract

The reaction of alkyl-lithium compounds, possessing α-hydrogens, or benzylmagnesium chloride with aromatic nitriles, followed by hydrolysis, gives ketones, E- and Z-N¹-(1-arylalk-1-enyl)benzamidines, 2-alkyl-2,4,6-triaryldihydro-1,3,5-triazines, and 2,4,6-triaryl-1,3,5-triazines. Conditions for preparing the enamidines in useful yields were established. t-Butyl-lithium and phenyl-lithium with benzonitrile gave only the ketones and dihydrotriazines. Phenylmagnesium bromide gave only benzophenone.