Radical Haloazidation of 1,5-Enenitriles for Making <i>N</i> -Haloimines and Sequential Triazolation to Form Tricyclics

A new method for making N -haloimines by Mn-catalyzed radical haloazidation of 1,5-enenitriles with TMSN 3 and N -halosuccinimides is introduced. The resulting azido N -haloimines are used for diannulation with alkynes to form triazole-fused heterocycles via a cascade CuAAC with alkynes and intramolecular electrophilic aromatic substitution (EAS).