Copper-catalyzed Addition Reactions of Aromatics and Ketones to 2-Aza-2,4-cyclopentadienone: Facile and Efficient Transformation of Carbonyl-ene-nitriles to 1H-Pyrrolin-2(5H)-ones

摘要

Copper-catalyzed reactions of carbonyl-ene-nitriles with carbon nucleophiles, such as aromatics and ketones, afforded pyrrolin-2-ones (gamma-lactam) in excellent yield. The reaction mechanism involves addition reactions with a ketimine moiety of the 2-aza-2,4-cyclopentadienone intermediate, which is formed via hydration of a nitrile moiety followed by dehydrative cyclization.