STUDIES IN THE BENZAZOLE AND NAPHTHAZOLE SERIES. VIII. REACTION OF 2-HYDRAZINONAPHTH[1,2-<i>d</i>]IMIDAZOLE AND ITS 1- AND 3-METHYL DERIVATIVES WITH CARBON DISULFIDE

Abstract

When heated with carbon disulfide in pyridine 2-hydrazinonaphth[1, 2-d]imidazole yields S-triazolo[4, 3-b]-naphth[1, 2-d]imidazole-3-thione. Kinetic and not steric factors determine the formation of this compound. Its trans-angular structure is demonstrated by the agreement between its UV spectrum and that of 11-methyl-S-triazolo[4, 3-b]naphth[1, 2-d]imidazole-3-thione, prepared from 1-methyl-2-hydrazinonaphth[1, 2-d]imidazole and carbon disulfide, as well as by the identity of their methylation products. Methyl iodide methylation, in the presence of sodium methoxide, of S-triazolo[4, 3-b]naphth[1, 2-d]imidazole-3-thione, like that of S-triazolo[4, 3-a]benzimidazole-3-thione, takes place stepwise. First the methyl group adds to the nitrogen atom of the imidazole ring, and only then to the thiol group of the triazole ring.

Authors: I. N. Getsova, L. L. Sribnaya, N. P. Bednyagina.

English Translation in Chemistry of Heterocyclic Compounds, 1965, 1 (1), pp 89-91

http://link.springer.com/article/10.1007/BF01168931