Herein, we report a practical and efficient carbon-to-nitrogen atom swap in 2-phenylimidazo[2,1-a]isoquinoline and 2-phenylimidazo[1,2-a]quinoline scaffolds, enabling their direct conversion to the corresponding 2-phenyl-[1,2,4]triazolo[5,1-a]isoquinoline and 2-phenyl-[1,2,4]triazolo[1,5-a]quinoline analogues. This transformation exploits the intrinsic reactivity of the parent heterocycles to undergo a cascade sequence involving oxidative cleavage, amination, and cyclization (OCAC) under mild conditions with functional group tolerance.