Synthesis of 1,2,4-triazepine and 1,2,5-triazocine derivatives from the reaction of 2-aminobenzohydrazide with π-acceptors

Abstract

The formation of metal complexes with acid hydrazides plays an important role in the growth of their biological activity. A simple synthetic strategy is described for the synthesis of novel 1,2,4-tri-azepine and 1,2,5-triazocine derivatives via electron donor–acceptor interaction. Thus when 2-aminobenzohydrazide reacted with tetracyanoethylene (TCNE) and 2-dicyanomethylene-indan-1,3-dione (CNIND) afforded 1,2,4-triazepine derivatives. While on reacting 1 with 2,3-dicyano-5,6-dichloro-1,4-benzoquinone (DDQ), 2,3-dichloro-1,4-naphthoquinone (DCHNQ), 1,4-naphthoquinone and/or 2,3,5,6-tetrabromo-1,4-benzoquinone, 1,2,5-triazocine derivatives were formed.