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.
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Kodak Soc. Anon., Belg. Pat. 559022 (1957); C. A., 54, 132, 1960.
N. P. Bednyagina, I. Ya. Postovskii, Summary, VIII Mendeleev Conference, Org. Chem. Section, 331, AN SSSR, 1959.
N. P. Bednyagina, I. I. Getsova, ZhOrKh, no. 1, 1965.
N. P. Bednyagina, I. N. Getsova, and I. Ya. Postovskii, ZhOKh, 32, 3011, 1962.
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For Part VII see [3].
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Getsova, I.N., Sribnaya, L.L. & Bednyagina, N.P. Studies in the benzazole and naphthazole series. VIII. Reaction of 2-hydrazinonaphth[1, 2-d]imidazole and its 1- and 3-methyl derivatives with carbon disulfide. Chem Heterocycl Compd 1, 89–91 (1965). https://doi.org/10.1007/BF01168931
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DOI: https://doi.org/10.1007/BF01168931