Сyclization of 1-amino-2-hydrazinobenzimidazole treated with carbon disulfide. Synthesis of 9-amino-2,9-dihydro-3Н-[1,2,4]triazolo[4,3-а]benzimidazole-3-thione and its derivatives

Resumo

1-Amino-2-hydrazinobenzimidazole when treated with carbon disulfide underwent a regioselective cyclization involving the hydrazino group to form 9-amino-2,9-dihydro-3Н-[1,2,4]triazolo[4,3-а]benzimidazole-3-thione. Being an N-amine this compound gives Schiff bases with aromatic aldehydes, and as thione in DMF at a temperature not exceeding 60°С it is successfully alkylated, particularly by functionalized alkylating agents, affording the corresponding sulfanylmethyl derivatives. In boiling DMF, as it is demonstrated by an example of benzyl chlorides, NNH₂ group also undergoes alkylation that unexpectedly results in 4-benzylidenamino-3-benzylsulfanyltriazolobenzimidazoles.