Skip to main content
Log in

A facile and effective procedure for synthesis of polyfunctionalized pyrrolines from simultaneously stirring of carbon disulfide, aniline, arylglyoxals and β-enaminocarbonyls

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

An efficient one-pot synthesis of 2H-pyrroline derivatives by a four-component reaction between carbon disulfide, aniline, arylglyoxals and β-enaminocarbonyls in acetonitrile at room temperature under mild reaction conditions is reported. The addition reaction has been done to access broad range of 5-hydroxy-4-phenylcarbamodithioate 2-H pyrroline derivatives after about 6 h stirring. All reactions were performed in acetonitrile at room temperature. Reactions are clean, and products were isolated by simple filtration.

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.

Scheme 1
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. J. Zhu, H. Bienayme (eds.), Multicomponent Reactions (Wiley, Weinheim, 2005)

    Google Scholar 

  2. B. Henkel, M. Sax, A. Dömling, Tetrahedron Lett. 44, 3679–3682 (2003)

    Article  CAS  Google Scholar 

  3. R.W. Waller, L.J. Diorazio, B.A. Taylor, W.B. Motherwell, T.D. Sheppard, Tetrahedron 66, 6496–6507 (2010)

    Article  CAS  Google Scholar 

  4. I. Yavari, Z. Hossaini, M. Sabbaghan, Mol. Divers. 10, 479–482 (2006)

    Article  CAS  Google Scholar 

  5. V.S.R. Chunduru, V.R. Rao, J. Sulfur Chem. 31, 545–550 (2010)

    Article  CAS  Google Scholar 

  6. I. Yavari, M.J. Bayat, M. Sirouspour, S. Souri, Tetrahedron 66, 7995–7999 (2010)

    Article  CAS  Google Scholar 

  7. M. Bayat, H. Imanieh, N. Zabarjad, N.Z. Shiraz, M.S. Qavidel, Monatshefte Chem. 141, 333–338 (2010)

    Article  CAS  Google Scholar 

  8. A. Ramazani, F.Z. Nasrabadi, Y. Ahmadi, Helv. Chim. Acta 94, 1024–1029 (2011)

    Article  CAS  Google Scholar 

  9. A. Ramazani, N. Shajari, A. Mahyari, Y. Ahmadi, Mol. Divers. 15, 521–527 (2011)

    Article  CAS  Google Scholar 

  10. A. Ramazani, T.A. Mahyari, M. Rouhani, A. Rezaei, Tetrahedron Lett. 50, 5625–5627 (2009)

    Article  CAS  Google Scholar 

  11. B. Alcaide, P. Almendros, C. Aragoncillo, R. Callejo, M.P. Ruiz, M.R. Torres, Eur. J. Org. Chem. 2012, 2359–2366 (2012)

    Article  CAS  Google Scholar 

  12. N.K. Terret, M. Gardner, D.W. Gordon, R.J. Kobylecki, J. Steel Tetrahedron. 51, 8135 (1995)

    Article  Google Scholar 

  13. I. Yavari, S. Beheshti, J. Iran. Chem. Soc. 8, 1030 (2011)

    Article  CAS  Google Scholar 

  14. H. Kakeya, C. Onozawa, M. Sato, K. Arai, H. Osada, J. Med. Chem. 40, 391 (1997)

    Article  CAS  Google Scholar 

  15. B.A. Kulkarani, A. Ganesan, Angew. Chem. Int. Ed. Engl. 36, 2454 (1997)

    Article  Google Scholar 

  16. S. Bienz, C. Busacca, A.I. Mayers, J. Am. Chem. Soc. 111, 1905 (1989)

    Article  CAS  Google Scholar 

  17. B. Tarnchompoo, C. Thebtaranonth, Y. Thebtaranonth, Tetrahedron Lett. 28, 6675 (1987)

    Article  CAS  Google Scholar 

  18. J. Hartung, C. Schur, I. Kempter, T. Gottwald, Tetrahedron 66, 1365–1374 (2010)

    Article  CAS  Google Scholar 

  19. A.L.J. Beckwith, C.H. Schiesser, Org. Biomol. Chem. 9, 1736–1743 (2011)

    Article  CAS  Google Scholar 

  20. C. Schur, N. Becker, U. Bergstraesser, J. Hartung, T. Gottwald, Tetrahedron 67, 2338–2347 (2011)

    Article  CAS  Google Scholar 

  21. V. Alagarsamy, U.S. Pathak, Bioorg. Med. Chem. 15, 3457–3462 (2007)

    Article  CAS  Google Scholar 

  22. P. Das, C.K. Kumar, K.N. Kumar, M. Innus, J. Iqbal, N. Srinivas, Tetrahedron Lett. 49, 992–995 (2008)

    Article  CAS  Google Scholar 

  23. K. Gobis, H. Foks, Z. Zwolska, Heterocycles 81, 917–934 (2010)

    Article  CAS  Google Scholar 

  24. W.D. Rudorf, J. Sulfur Chem. 28, 295–339 (2007)

    Article  CAS  Google Scholar 

  25. I. Yavari, M. Sirouspour, S. Souri, Monatshefte Chem. 49, 141 (2010)

    Google Scholar 

  26. J.L. Cui, Z.M. Ge, T.M. Cheng, R.T. Li, Synth. Commun. 33, 1969 (2003)

    Article  CAS  Google Scholar 

  27. N. Azizi, B. Pourhasan, F. Aryanasab, M.R. Saidi, Synlett 8, 1239 (2007)

    Google Scholar 

  28. J. Safaei-Ghomi, F. Salimi, A. Ramazani, J. Chem. Sci. 125, 1087–1092 (2013)

    Article  CAS  Google Scholar 

  29. H.L. Riley, J.F. Morley, N.A.C. Friend, Chem. Soc. 1, 1875 (1932)

    Article  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge, Islamic Azad University, Rafsanjan branch for financial support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mozhgan Masoudi.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 45 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Masoudi, M., Anary-Abbasinejad, M. & Maleki, A. A facile and effective procedure for synthesis of polyfunctionalized pyrrolines from simultaneously stirring of carbon disulfide, aniline, arylglyoxals and β-enaminocarbonyls. J IRAN CHEM SOC 14, 2299–2304 (2017). https://doi.org/10.1007/s13738-017-1166-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-017-1166-1

Keywords

Navigation