Synthesis and solvolysis of arylidene-1-methyl-1H-tetrazol-5-yl-hydrazidic bromides: a route to 6-aryl-3-methyl[1,2,4]triazolo[4,3-d]-tetrazoles

Abstract

Bromination of arylidene-1-methyl-1H-tetrazol-5-ylhydrazines yielded the corresponding hydrazidic bromides. Solvolysis of these materials in aqueous solvents resulted in the formation of fused triazolotetrazoles. This reaction which involves the tetrazole ring as a nucleophile was, under appropriate conditions, competed against by the solvent water, or by added nucleophiles such as acetate, and it was eliminated when a highly nucleophilic solvent such as aniline was used. Some further reactions of the hydrazidic bromides are also discussed.