C–H Amination of Nitro Azaheterocyclic Compounds by Vicarious Nucleophilic Substitution

Abstract

This manuscript describes the C-H amination of a variety of nitro aza-heterocyclic compounds by Vicarious Nucleophilic Substitution (VNS) methodology with 4-amino-1,2,4-triazole (ATA). The aminated products were characterized by NMR, MS and single-crystal X-ray diffraction. Among the substrates examined, moderate to excellent yield (30-88%) and good regioselectivity (ortho/para position of the nitro) are exhibited. This protocol offers the advantages of mild conditions, short reaction time (only 2-4 h) with inexpensive, commercially available and less toxic amination reagent, no additional catalysts or reagents needed. Possible reaction mechanism was also discussed.