Abstract
2-Benzothiazolylhydrazones were synthesized by the action of bromine on 4-arylthiosemicarbazones. The imino structure of the cyclization products was demonstrated by comparison of the UV spectra of the hydrazones and the methylation product. Cyclization to the thiadiazole derivative was noted when bromine was present in the aryl ring of the thiosemicarbazone. A dimethylamino group in the aldehyde portion of the molecule prevents cyclization.
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I. L. Shegal, G. N. Tyurenkova, and I. Ya. Postovskii, Khim. Geterotsikl. Soed., 570 (1967).
A. Hugerschoff, Ber.,34, 3130 (1901);36, 3121 (1903).
N. P. Bednyagina, N. V. Serebryakova, and G. N. Lipunova, Khim. Geterotsikl. Soed., 342 (1967).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1330–1332, October, 1970.
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Shegal, L.M., Shegal, I.L. Oxidative cyclization of 4-arylthio-semicarbazones. Chem Heterocycl Compd 6, 1238–1240 (1970). https://doi.org/10.1007/BF00755065
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DOI: https://doi.org/10.1007/BF00755065