Inter-and intramolecular transition metal-catalyzed amination of 2-chloro-3-iodopyridine and 2, 3-dibromopyridine, respectively, with benzodiazinamines yielded six hitherto unknown tetracyclic azaheteroaromatic cores. C–N bond formation was achieved via auto-tandem (Pd- catalyst) as well as one-pot (sequential use of a Pd-and Cu-catalyst) catalysis.