Reactions between enaminones and enones. Part 2. Alkylation of enaminones with acrylic esters

Abstract

The anion of 3-amino-5,5-dimethylcyclohex-3-enone (1) reacts with ethyl acrylate to give the product of C- or N-alkylation, depending on the conditions. With methyl methacrylate or methyl crotonate, the major product results from N-alkylation, but this reacts further to give a 1,3-bis(3-oxocyclohex-1 -enylamino)-propan-1 -one. Evidence for the mechanism of this reaction is presented. The structure of an unidentified by-product from Part 1 is given.