2‐Pyridylenamines via transenamination

Abstract

Transenamination, a reaction apparently not previously described in the literature, has been employed to prepare a series of 2‐pyridylenamines. The products were formed in 11‐78% yield by the reaction of substituted 2‐arninopyridines, 1a‐g, and either methyl 3‐aminocrotonate, 2, or ethyl 3‐aminocinnamate, 3, in anhydrous toluene, under reflux. Data from these reactions would suggest that the reaction rates and consequently, the yields, were adversely affected by substitution that served to decrease the basicity of the amino group in either reactant.