Regioselective halogenation of pyridinium N-(benzoazynyl) aminides as a way to produce N-benzyl-α-aminobenzoazines

Abstract The halogenation of pyridinium N -(benzoazynyl) aminides with N -halosuccinimides provides a mild and regioselective method to functionalize the negatively charged diazine moiety in most cases. In some examples, however, formation of other products is explained. Finally, alkylation of the exocyclic nitrogen and reduction of the N–N bond provides a simple and straightforward strategy to obtain functionalized N -benzyl-benzoazynyl-α-amines.