The first example of copper-catalyzed sequential arylation and intramolecular annulation of 2-(2-bromophenyl)-2,3-dihydroquinazolin-4(1H)-ones with alkyl amidines has been developed for the synthesis of 6-alkyl 11bH-quinazolino[3,4-a]quinazolin-13(12H)-ones (3) in moderate to good yields. However, the arylation products N-(2-(4-oxo-1,2,3,4-tetrahydroquinazolin-2-yl)phenyl)benzimidamides (4) are isolated when aryl amidines are used in the transformation. The results revealed that the successive intramolecular annulation does significantly depend on the substituents on the amidines. It is noteworthy that the arylation products 4 can be transformed into 6-aryl 11bH-quinazolino[3,4-a]quinazolin-13(12H)-ones (3) via intermolecular annulation.