A new approach for the facile synthesis of fused quinazolinone scaffolds through a palladium-catalyzed carbonylative coupling followed by an intramolecular nucleophilic aromatic substitution is described. The base serves as the key modulator: Whereas DBU gives rise to the linear isomers, Et 3N promotes the preferential formation of angular products. Interestingly, a light-induced 4+4 reaction of the product was also observed. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.