Advertisement

Russian Journal of Organic Chemistry

, Volume 44, Issue 6, pp 849–854 | Cite as

New syntheses on the basis of ethyl 2-oxotetrahydrofuran-3-carboxylates

  • T. V. Kochikyan
  • E. V. Arutyunyan
  • V. S. Arutyunyan
  • A. A. Avetisyan
Article

Abstract

Alkylation of 5-substituted ethyl 5-methyl-2-oxotetrahydrofuran-3-carboxylates with alkyl halides in the presence of sodium ethoxide gave the corresponding 3-alkyl derivatives which were converted into 3,5-substituted 5-methyl-N-(4-nitrophenyl)-2-oxotetrahydrofuran-3-carboxamides and 5-methyltetrahydrofuran-2-ones. Reactions of the latter with hydrazine hydrate led to the formation of 4-hydroxypentanoic acid hydrazides which were treated with isothiocyanates to obtain the corresponding thiosemicarbazides whose intramolecular cyclization in the presence of aqueous alkali gave previously unknown 1,2,4-triazole-3-thiol derivatives.

Keywords

Lactone Hydrazine Hydrate Sodium Ethoxide Hydrazinecarbothioamide Butanolides 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Sicman, D.V., Kamlet, M.J., Rich, R.D., Heller, H., and Kaplan, L.A., US Patent no. 3 745 076; Chem. Abstr., 1973, vol. 79, no. 94 198 b.Google Scholar
  2. 2.
    Brois, S.J. and Gutierres, A., US Patent no. 4 062 786; Chem. Abstr., 1978, vol. 89, no. 27 341 m.Google Scholar
  3. 3.
    Arutyunyan, V.S., Kochikyan, T.V., Avetisyan, A.A., and Kinzirskii, A.S., Sbornik statei Respublikanskogo Gematologicheskogo tsentra (Collection of Papers of the Republican Hematological Center), Erevan, 1998, p. 409.Google Scholar
  4. 4.
    Kochikyan, T.V., Arutyunyan, E.V., Arutyunyan, V.S., and Avetisyan, A.A., Russ. J. Org. Chem., 2002, vol. 38, p. 390.CrossRefGoogle Scholar
  5. 5.
    Arutyunyan, V.S., Kochikyan, T.V., Arutyunyan, E.V., and Avetisyan, A.A., Khim. Zh. Arm., 2002, vol. 55, p. 72.Google Scholar
  6. 6.
    Kochikyan, T.V., Arutyunyan, V.S., Arutyunyan, E.V., and Avetisyan, A.A., Russ. J. Org. Chem., 2003, vol. 39, p. 1140.CrossRefGoogle Scholar
  7. 7.
    Kochikyan, T.V., Synth. Commun., 2004, vol. 34, p. 4219.CrossRefGoogle Scholar
  8. 8.
    Kochikyan, T.V., Samvelyan, M.A., Arutyunyan, V.S., and Avetisyan, A.A., Khim. Geterotsikl. Soedin., 2005, no. 11, p. 1625.Google Scholar
  9. 9.
    Kochikyan, T.V., Samvelyan, M.A., Arutyunyan, V.S., and Avetisyan, A.A., Russ. J. Org. Chem., 2003, vol. 39, p. 1329.CrossRefGoogle Scholar
  10. 10.
    Kochikyan, T.V., Samvelyan, M.A., Harutyunyan, V.S., and Avetisyan, A.A., Synth. Commun., 2006, vol. 36, p. 1613.CrossRefGoogle Scholar
  11. 11.
    Demirbas, N., Ugurluoglu, R., and Demirbas, A., Bioorg. Med. Chem., 2002, vol. 10, p. 3717.CrossRefGoogle Scholar
  12. 12.
    Upadhayaya, R.S., Sinha, N., Jain, S., Kishore, N., Chandra, R., and Arora, S.K., Bioorg. Med. Chem., 2004, vol. 12, p. 2225.CrossRefGoogle Scholar
  13. 13.
    Saghiyan, A.S., Geolchanyan, A.V., Petrosyan, S.G., Chochikyan, T.V., Harutyunyan, V.S., Avetisyan, A.A., Belokon, Yu.N., and Visher, K., Tetrahedron: Asymmetry, 2004, vol. 15, p. 705.CrossRefGoogle Scholar
  14. 14.
    Saghiyan, A.S., Geolchanyan, A.V., Manasyan, L.L., Mkrtchyan, G.M., Martirosyan, N.R., Dadayan, S.A., Kochikyan, T.V., Harutyunyan, V.S., Avetisyan, A.A., Tararov, V.I., Maleev, B.I., and Belokon, Yu.N., Russ. Chem. Bull., 2004, vol. 53, p. 932.CrossRefGoogle Scholar
  15. 15.
    Arutyunyan, V.S., Kochikyan, T.V., Arutyunyan, E.V., and Avetisyan, A.A., Khim. Zh. Arm., 2000, vol. 53, p. 121.Google Scholar
  16. 16.
    Arakelyan, S.V., Akopyan, S.M., Titanyan, S.G., and Dangyan, M.T., Uch. Zap. Erevan. Gos. Univ., 1972, vol. 1, p. 122.Google Scholar

Copyright information

© MAIK Nauka 2008

Authors and Affiliations

  • T. V. Kochikyan
    • 1
  • E. V. Arutyunyan
    • 1
  • V. S. Arutyunyan
    • 1
  • A. A. Avetisyan
    • 1
  1. 1.Erevan State UniversityErevanArmenia

Personalised recommendations