REGIO- AND DIASTEREOSELECTIVE SYNTHESIS OF N-SUBSTITUTED 2-ACYL-3-ARYL-3,5-DIHYDROFURO[3,2-c]PYRIDIN-4(2H)-ONES

Abstract

The three-component condensation of pyridinium acylmethylides generated in situ with aromatic aldehydes and 4-hydroxy-6-methylpyridones gave a series of 2-acyl-3-aryl-3,5-dihydrofuro[3,2-c]pyridin-4(2H)-ones. The reaction proceeds diastereoselectively with the formation of trans-isomers and represents a cascade process involving the Knoevenagel condensation, the carbo-Michael reaction, and intramolecular nucleophilic substitution.