Aromatic vs Diene Reactivity of 2(1H)-Pyridinone and Its Derivatives.

Abstract The reaction of 2(1H)-pyridinone and some of its derivatives with substituted propynenitriles was studied. The aromatic character of 1-methyl-2(1H)-pyridinone is reflected in its failure to give a 4 +2 adduct. Instead, reaction occurs at lactam carbonyl function to give 1,2-dihydropyridine-2-methides. The O-methyl derivatives are dealkylated during reaction with propynenitriles to give N-substituted pyridones which are otherwise accessible in good yields from 2(1H)-pyridinone.