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4-Acetyl-1-(R-benzylidene)-3-(5-nitro-2-furfuryl)thiosemicarbazides — Carriers of synthones for obtaining thiazole and triazole rings

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The corresponding thiosemicarbazonium salts, which form 4-acetyl- and 2,4-di-acetyl-1-benzylidene-3-(5-nitro-2-furfuryl)thiosemicarbazides with acetic anhydride, were obtained by the reaction of 5-nitrofurfuryl bromide with 1-benzyl-idenethiosemicarbazides. Under the influence of bases the monoacetylated derivatives undergo cyclization to the corresponding 2-benzylidenehydrazino-5-(5-nitro-2-furyl)thiazoles. Intramolecular cyclization of the monoacetylated products to 3-methyl-5-[(5-nitro-2-furfuryl)thio]-1,2,4-triazole, which is accompanied by the elimination of the corresponding benzaldehyde, occurs in the presence of hydrochloric acid.

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Literature Cited

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Authors and Affiliations

  1. Krasnodar Polytechnical Institute, 350700, Krasnodar

    G. D. Krapivin, E. B. Usova & V. G. Kul'nevich

Authors
  1. G. D. Krapivin
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  2. E. B. Usova
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  3. V. G. Kul'nevich
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 699–704, May, 1988.

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Krapivin, G.D., Usova, E.B. & Kul'nevich, V.G. 4-Acetyl-1-(R-benzylidene)-3-(5-nitro-2-furfuryl)thiosemicarbazides — Carriers of synthones for obtaining thiazole and triazole rings. Chem Heterocycl Compd 24, 573–578 (1988). https://doi.org/10.1007/BF00755702

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  • DOI: https://doi.org/10.1007/BF00755702

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