Mechanism study of base-catalyzed cyclization of 2-nitrophenylhydrazine in aqueous solution

The mechanism of cyelizalion of 2-nitrophenylhydrazine to 1-hydroxybenztriazole in alkaline aqueous solutions is studied. Kinetic parameters, product distribution and activation parameters are determined. A mechanism involving direct attack of the β-hydrazino nitrogen on the nitrogen ol the nilro group with elimination of water is postulated. Substituted 2-nitrophenylhydrazines are synthesized and studied under the same conditions.