We　present　a　novel　Cu-catalyzed　aromatic　metamorphosis　of　3-aminoindazoles　via　oxidative　cleavage　of　two　C-N　bonds　of　3-aminoindazoles.　This　unprecedented　reactivity　of　3-aminoindazoles　allows　one　to　forge　diverse　nitrile-containing　triphenylenes　in　decent　yields　via　generation　of　the　cyano　group　in　situ.　The　current　study　reveals　that　3-aminoindazoles　could　be　harnessed　as　radical　precursors　via　oxidative　denitrogenation,　the　reaction　mechanism　of　which　was　supported　by　density　functional　theory　calculations.