Reaction of 1, l'-Bis(methoxycarbonyl)divinylamine with Primary Amines —Formation of 3-Pyrrolin -2-one Derivatives—

Abstract

The reaction of 1, 1'-bis(methoxycarbonyl)divinylamine (BDA) with primary amines was investigated as an example of nucleophilic attack on a cross-conjugated dienamine. BDA reacted with primary amines to yield azomethines [5]-[8], which supported the reaction mechanism involving a nucleophilic attack of primary amines at the electron deficient α-carbon atom of the enamine form of BDA, followed by an elimination of methyl 2-aminoacrylate. In these reactions, unexpected 3-pyrrolin-2-ones [10]-[13]were also isolated and their structures were determined by means of IR and 1H-NMR spectra.