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Chemistry of Heterocyclic Compounds

, Volume 19, Issue 2, pp 137–141 | Cite as

Synthesis and transformations of carbohydrate derivatives. 1. Synthesis of furan and 5-nitrofuran derivatives of some thiosemicarbazones and thiosemicarbazides of D-glucose and L-arabinose

  • A. A. Tashpulatov
  • V. A. Afanas'ev
  • M. Yu. Lidak
  • N. M. Sukhova
  • Yu. Yu. Popelis
  • I. Rakhmatullaev
Article

Abstract

N-Glycopyranosylthiosemicarbazones and their acetates were synthesized by the reaction of tetraacetylglycopyransyl isothiocyanates with hydrazones of furan and nitrofuran aldehydes and also by reaction with hydrazine hydrate and subsequent treatment with the aldehydes. Acetates of glycopyranosyl-5-R-furoylthiosemicarbazides were obtained by acetylation of glycopyranosylthiosemicarbazides with furan- and 5-nitrofuranocarboxylic acid chlorides. The structures of the synthesized compounds were confirmed by thin-layer chromatography and the IR and PMR spectra and by the results of elementary analysis.

Keywords

Acetate Hydrate Carbohydrate Aldehyde Hydrazine 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Literature cited

  1. 1.
    K. Miura and H. K. Reckendorf, Progress in Medicinal Chemistry, Vol. 5, London (1967), p. 320.Google Scholar
  2. 2.
    D. R. McCalla, Nitrofurans. Reprint from Antibiotics VI, Mechanism of the Action of Antibacterial Agents, F. H. Hahn, ed., Heidelberg-New York (1979), p. 176.Google Scholar
  3. 3.
    V. A. Kul'skin, R. G. Macharadze, S. E. Zurabyan, A. Ya. Khorlin, and M. L. Shul'man, USSR Inventor's Certificate No. 666182; Byull. Izobret., No. 21, 81 (1979).Google Scholar
  4. 4.
    E. Fisher, Chem. Ber., 47, 1377 (1914).Google Scholar
  5. 5.
    J. Jasinska, Roczn. Chem., 45, 1641 (1971).Google Scholar
  6. 6.
    H. Booth, Tetrahedron Lett., 7, 411 (1965).Google Scholar
  7. 7.
    Yu. Yu. Popelis, É. É. Liepin'sh, and Ya. P. Stradyn', Khim. Geterotsikl. Soedin., No. 2, 167 (1980).Google Scholar
  8. 8.
    G. Zemplen, Chem. Ber., 69, 1827 (1936).Google Scholar
  9. 9.
    C. Gmernicka-Haftek, Z. Nowakowska, M. Wojtowicz, I. Bogacka, and B. Borkowski, Acta Pol. Pharm., 2, 139 (1979).Google Scholar
  10. 10.
    Barcrai-Martos and F. Körösy, Nature, 165, 369 (1950).Google Scholar
  11. 11.
    Yu. K. Yur'ev, R. Ya. Levina, and Yu. S. Shabarov, in: Practical Studies in Organic Chemistry [in Russian], Vol. 4, Izd. Moskovsk. Gos. Univ., Moscow (1969), p. 145.Google Scholar
  12. 12.
    Roy Hull, British Patent No. 816886; Chem. Abstr., 55, 24791 (1961).Google Scholar
  13. 13.
    A. A. Ponomarev, Syntheses and Reactions of Furan Substances [in Russian], Izd. Saratovsk. Univ. (1960), pp. 161, 165.Google Scholar

Copyright information

© Plenum Publishing Corporation 1983

Authors and Affiliations

  • A. A. Tashpulatov
    • 1
    • 2
  • V. A. Afanas'ev
    • 1
    • 2
  • M. Yu. Lidak
    • 1
    • 2
  • N. M. Sukhova
    • 1
    • 2
  • Yu. Yu. Popelis
    • 1
    • 2
  • I. Rakhmatullaev
    • 1
    • 2
  1. 1.Institute of Organic ChemistryAcademy of Sciences of the Kirghiz SSRFrunze
  2. 2.Institute of Organic SynthesisAcademy of Sciences of the Latvian SSRRiga

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