Synthesis of some 3-cyano5,6-dihydropyridines-2-ones and their n-substituted derivatives

ABSTRACT

3-Cyano-5,6-dihydro-4,6-disubstituted-6-methylpyridin-2-ones [2a-d] were prepared by condensation of methyl ketones and ethyl cyanoacetate in a 21 molar ratio in presence of ammonium acetate. The obtained pyridones [2a] and 2b] add diethyl acetylenedicarboxylate, acrylonitrile and methyl acrylate to give the corresponding N-substituted derivatives 3, 4 and 5 respectively. Several reports have been published dealing with the reaction of ethyl cyanoacetate with c,[B-unsaturated ketones to give 3- cyano-4, 6-disubstituted pyridin-2- ones [1-7], some of which were found to possess a pronounced antimicrobial activity [6-7]. In the present work, some dihydropyridone derivatives and related compounds have been synthesized by the condensation of ethyl cyanoacetate with some methyl ketones