The efficient syntheses of 6,6,8,6,6-pentacyclic naphtho-fused oxazocinoquinolinones and 6,6,8,6,6,6-hexacyclic benzo[g]quinoxalino-fused oxazocinoquinolinones were achieved in one-pot sequences. The generation of libraries of their diaryl- and alkynyl-substituted analogues via Suzuki-Miyaura and Sonogashira cross-coupling reactions, respectively, were also achieved. © Georg Thieme Verlag Stuttgart.