After complexation with copper(II) ions, Schiff bases 1a-d may undergo an oxidative ring closure using atmospheric oxygen to give a number of imidazo[1,5-a]pyridines 2, an imidazo[1,5-a]imidazole 3, and an imidazo[5,1-a]isochinoline 4. This ligand oxidation can be performed with catalytic amounts of copper ions in the reaction. A catalytic cycle for the copper-catalyzed oxidative heterocyclization will be presented together with isolated copper complexes of Schiff bases 1a,b and intermediates 5 and 8 that were found by X-ray structure analyses which confirm this reaction scheme.