The synthesis of γ-lactam-substituted quinone derivatives through a Ag₂O-catalyzed cascade cyclization and functionalization of N-aryl-4-pentenamides has been developed. Related 2-oxazolidinone substituted quinone products can be also obtained with N-aryl allyl carbamates. The reactions proceed through an amidyl radical-initiated 5-exo-trig cyclization and followed radical addition to quinones. They provide an efficient route to various γ-lactam-substituted quinone derivatives with a wide range of substrate scope.