Herein, we present a tandem aza-Michael addition–vinylogous aldol condensation strategy for the synthesis of N-bridged pyridine fused quinolone derivatives from quinolones and ynones. The presented tandem transformation features the construction of C–N and CC bonds in a single operation, under transition metal-free conditions. The wide substrate scope and gram scale synthesis of pyridine fused quinolone derivatives expand the synthetic value of the presented protocol.