Skip to main content
Log in

Synthesis of Novel 2-(N-Substituted)imino-2,5-dihydrofuran-3-carboxamides Containing a Thiourea Residue and an Oxothiazolidinylidene Ring

  • Short Communications
  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Novel derivatives of 2-imino-2,5-dihydrofuran-3-carboxamides containing a thiourea residue have been synthesized by the reaction of 2-imino-2,5-dihydrofuran-3-carboxamides with thiosemicarbazide in glacial acetic acid. The synthesized N-substituted iminodihydrofurans have been condensed with ethyl chloroacetate to obtain novel derivatives of iminodihydrofurans containing an oxothiazolidinylidene ring. These methods open up new synthetic approaches to previously unknown systems containing iminodihydrofuran, thiourea and oxothiazolidinylidene fragments.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

References

  1. Avetisyan, A.A. and Tokmadzhyan, G.G., Khim. Zh. Arm., 2007, vol. 60, p. 698.

    CAS  Google Scholar 

  2. Cheikh, N., Bar, N., Choukchou-Braham, N., Mostefa-Kara, B., Lohier, J.-F., Sopkova, J., and Villemin, D., Tetrahedron, 2011, vol. 67, p. 1540. https://doi.org/10.1016/j.tet.2010.12.062

    Article  CAS  Google Scholar 

  3. Avetissyan, A. and Karapetyan, L., Synth. Commun., 2009, vol. 39, p. 7. https://doi.org/10.1080/00397910701739022

    Article  CAS  Google Scholar 

  4. Avetisyan, A.A. and Karapetyan, L.V., Russ. J. Org. Chem., 2009, vol. 45, p. 1578. https://doi.org/10.1134/S1070428009100303

    Article  CAS  Google Scholar 

  5. Avetisyan, A.A., Karapetyan, L.V., and Tadevosyan, M.D., Russ. J. Org. Chem., 2009, vol. 45, p. 1031. https://doi.org/10.1134/S1070428009070082

    Article  CAS  Google Scholar 

  6. Avetisyan, A.A., Karapetyan, L.V., and Tadevosyan, M.D., Russ Chem Bull., 2010, vol. 59, p. 974. https://doi.org/10.1007/s11172-010-0192-2

    Article  CAS  Google Scholar 

  7. Karapetyan, L., Monatsh. Chem., 2012, vol. 143, p. 687. https://doi.org/10.1007/s00706-011-0615-2

    Article  CAS  Google Scholar 

  8. Avetisyan, A.A., Karapetyan, L.V., and Tadevosyan, M.D., Russ. J. Org. Chem., 2010, vol. 46, p. 1259. https://doi.org/10.1134/S1070428010080257

    Article  CAS  Google Scholar 

  9. Avetisyan, A.A. and Karapetyan, L.V., Heterocycl. Commun., 2012, vol. 18, p. 263. https://doi.org/10.1515/hc-2012-0113

    Article  CAS  Google Scholar 

  10. Tokmajyan, G.G. and Karapetyan, L.V., J. Heterocycl. Chem., 2017, vol. 54, p. 1630. https://doi.org/10.1002/jhet.2713

    Article  Google Scholar 

  11. Le Tiran, A., Stables, J.P., and Kohn, H., Bioorg. Med. Chem., 2001, vol. 9, p. 2693. https://doi.org/10.1016/S0968-0896(01)00204-8

    Article  Google Scholar 

  12. Somsák, L., Kovács, L., Tóth, M., Osz, E., Szilágyi, L., Györgydeák, Z., Dinya, Z., Docsa, T., Tóth, B., and Gergely, P., J. Med. Chem., 2001, vol. 44, p. 2843. https://doi.org/10.1021/jm010892t

    Article  Google Scholar 

  13. Lerchen, H.-G., Baumgarten, J., von dem Bruch, K., Lehmann, T.E., Sperzel, M., Kempka, G., and Fiebig, H.-H., J. Med. Chem., 2001, vol. 44, p. 4186. https://doi.org/10.1021/jm010893l

    Article  CAS  Google Scholar 

  14. Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Moscow: Novaya Volna, 2010.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to L. V. Karapetyan.

Ethics declarations

The authors declare no conflict of interest.

Additional information

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 11, pp. 1796–1799.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Karapetyan, L.V., Tokmajyan, G.G. & Makaryan, G.M. Synthesis of Novel 2-(N-Substituted)imino-2,5-dihydrofuran-3-carboxamides Containing a Thiourea Residue and an Oxothiazolidinylidene Ring. Russ J Org Chem 55, 1806–1808 (2019). https://doi.org/10.1134/S1070428019110265

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428019110265

Keywords

Navigation