α-(4,6-Diphenyl-2-oxo-1-pyridyl)benzyl-lithiums and their reactions with electrophiles

Abstract

1-Benzyl-4,6-diphenyl-2-pyridone is lithiated by LiNPr^I₂ at the methylene carbon to form a carbanion which reacts with various electrophiles to give the corresponding 1-(α-substituted-benzyl)-4,6-diphenyl-2-pyridones. Potassium dimsylate converts 1-benzyl-4,6-diphenyl-2-pyridone into the 3-methyl derivative. The anion derived from 1-(α-methylbenzyl)-4,6-diphenyl-2-pyridone rapidly rearranges to the azepinone (18).