Condensation of dimethyl malonate with benzal-4-acetylanilines: A chemoselective reaction

Dimethyl malonate has reacted chemoselectively with carbon-nitrogen double bond of benzal-4-acetylanilines (1-8) leaving thc carbon-oxygen double bond, considered to be more reactive, intact under reaction conditions, leading to the formation of mono addition-elimination products rather than bis attack at both the double bonds, even when the reaction has been carried out with two moles of dimethyl malonate.