Skip to main content
Log in

1,3-Disulfonic acid benzimidazolium chloride as an efficient and recyclable ionic liquid catalyst for the synthesis of 3,4-dihydropyrimidine-2-(1H)-ones/thiones

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

1,3-Disulfonic acid benzimidazolium chloride ionic liquid ([Dsbim]Cl) was prepared, characterized and applied as an efficient, homogeneous and recyclable catalyst for the synthesis of 3,4-dihydropyrimidine-2-(1H)-ones/thiones through the one-pot three-component condensation of aromatic aldehydes, urea/thiourea and ethyl acetoacetate under solvent-free conditions. The key advantages of this novel protocol are its short reaction time, high yields, mild and clean conditions, practical simplicity and its capacity for reuse several times without a noticeable decrease in catalytic activity.

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
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Scheme 2
Fig. 5

Similar content being viewed by others

References

  1. A.M. Zonouz, I. Eskandari, H.R. Khavasi, Tetrahedron Lett. 53, 5519 (2012)

    Article  CAS  Google Scholar 

  2. J. Liu, M. Lei, L. Hu, Green Chem. 14, 2534 (2012)

    Article  CAS  Google Scholar 

  3. V.I. Parvulescu, C. Hardacre, Chem. Rev. 107, 2615 (2007)

    Article  CAS  Google Scholar 

  4. B. Xin, J. Hao, Chem. Soc. Rev. 43, 7171 (2014)

    Article  CAS  Google Scholar 

  5. R. Kurane, J. Jadhav, S. Khanapure, R. Salunkhe, G. Rashinkar, Green Chem. 15, 1849 (2013)

    Article  CAS  Google Scholar 

  6. M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Appl. Catal. A 400, 70 (2011)

    Article  CAS  Google Scholar 

  7. J. Pavlinac, M. Zupan, K.K. Laali, S. Stavber, Tetrahedron 65, 5625 (2009)

    Article  CAS  Google Scholar 

  8. S. Brauch, S.S. van Berkel, B. Westermann, Chem. Soc. Rev. 42, 4948 (2013)

    Article  CAS  Google Scholar 

  9. C.R. Cioc, E. Ruijter, R.V.A. Orru, Green Chem. 16, 2958 (2014)

    Article  CAS  Google Scholar 

  10. R. Ghorbani-Vaghei, Z. Salimi, S.M. Malaekehpoor, F. Eslami, S. Noori, RSC Adv. 4, 33582 (2014)

    Article  CAS  Google Scholar 

  11. P. Biginelli, Gazz. Chim. Ital. 23, 360 (1893)

    Google Scholar 

  12. R.H. Tale, A.H. Rodge, G.H. Hatnapure, A.P. Keche, Bioorg. Med. Chem. Lett. 21, 4648 (2011)

    Article  CAS  Google Scholar 

  13. T.N. Akhaja, J.P. Raval, Eur. J. Med. Chem. 46, 5573 (2011)

    Article  CAS  Google Scholar 

  14. F. Dong, L. Jun, Z. Xinli, Y. Zhiwen, L. Zuliang, J. Mol. Catal. A Chem. 274, 208 (2007)

    Article  CAS  Google Scholar 

  15. H. Khabazzadeh, K. Saidi, H. Sheibani, Bioorg. Med. Chem. Lett. 18, 278 (2008)

    Article  CAS  Google Scholar 

  16. O.M. Singh, S.J. Singh, M.B. Devi, L.N. Devi, N.I. Singh, S.G. Lee, Bioorg. Med. Chem. Lett. 18, 6462 (2008)

    Article  CAS  Google Scholar 

  17. F. Damkaci, A. Szymaniak, J. Chem. Educ. 91, 943 (2014)

    Article  CAS  Google Scholar 

  18. Q. Zhang, X. Wang, Z. Li, W. Wu, J. Liu, H. Wu, S. Cui, K. Guo, RSC Adv. 4, 19710 (2014)

    Article  CAS  Google Scholar 

  19. A. Debachea, M. Amimoura, A. Belfaitaha, S. Rhouatia, B. Carboni, Tetrahedron Lett. 49, 6119 (2008)

    Article  Google Scholar 

  20. S.R. Jetti, A. Bhatewara, T. Kadre, S. Jain, Chin. Chem. Lett. 25, 469 (2014)

    Article  CAS  Google Scholar 

  21. J.T. Starcevich, T.J. Laughlin, R.S. Mohan, Tetrahedron Lett. 54, 983 (2013)

    Article  CAS  Google Scholar 

  22. K. Konkala, N.M. Sabbavarapu, R. Katla, N.Y.V. Durga, T.V.K. Reddy, L.A.P.D. Bethala, R.B.N. Prasad, Tetrahedron Lett. 53, 1968 (2012)

    Article  CAS  Google Scholar 

  23. M. Moghaddas, A. Davoodnia, M.M. Heravi, N. Tavakoli-Hoseini, Chin. J. Catal. 33, 706 (2012)

    Article  CAS  Google Scholar 

  24. B.C. Ranu, A. Hajra, U. Jana, J. Org. Chem. 65, 6270 (2000)

    Article  CAS  Google Scholar 

  25. M.M. Amini, A. Shaabani, A. Bazgir, Catal. Commun. 7, 843 (2006)

    Article  CAS  Google Scholar 

  26. K.A. Kumar, M. Kasthuraiah, C.S. Reddy, C.D. Reddy, Tetrahedron Lett. 42, 7873 (2001)

    Article  Google Scholar 

  27. N.A. Liberto, S.P. Silva, A. de Fatima, S.A. Fernandes, Tetrahedron 69, 8245 (2013)

    Article  CAS  Google Scholar 

  28. Y. Qiu, H. Sun, Z. Ma, W. Xia, J. Mol. Catal. A Chem. 392, 76 (2014)

    Article  CAS  Google Scholar 

  29. H. Kiyani, M. Ghiasi, Res. Chem. Intermed. (2014). doi:10.1007/s11164-014-1766-7

    Google Scholar 

  30. F. Tamaddon, S. Moradi, J. Mol. Catal. A Chem. 370, 117 (2013)

    Article  CAS  Google Scholar 

  31. G.H. Mahdavinia, H. Sepehrian, Chin. Chem. Lett. 19, 1435 (2008)

    Article  CAS  Google Scholar 

  32. M. Nasr-Esfahani, J. Hoseini, F. Mohammadi, Chin. J. Catal. 32, 1484 (2011)

    Article  CAS  Google Scholar 

  33. S.D. Salim, K.G. Akamanchi, Catal. Commun. 12, 1153 (2011)

    Article  CAS  Google Scholar 

  34. M. Tajbakhsh, Y. Ranjbar, A. Masuodi, S. Khaksar, Chin. J. Catal. 33, 1542 (2012)

    Article  CAS  Google Scholar 

  35. S. Mohammadi, M. Abbasi, Res. Chem. Intermed. (2015). doi:10.1007/s11164-015-1934-4

    Google Scholar 

  36. S. Mohammadi, M. Abbasi, J. Chem. Res. 39, 123 (2015)

    Article  CAS  Google Scholar 

  37. M. Rahimizadeh, S.M. Seyedi, M. Abbasi, H. Eshghi, A. Khojastehnezhad, F. Moeinpour, M. Bakavoli, J. Iran. Chem. Soc. 12, 839 (2015)

    Article  CAS  Google Scholar 

  38. F. Shirini, N.G. Khaligh, J. Mol. Liq. 177, 386 (2013)

    Article  CAS  Google Scholar 

  39. F. Shirini, M. Abedini, R. Pourhasan-Kisomi, Chin. Chem. Lett. 25, 111 (2014)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

I gratefully acknowledge the Islamic Azad University of Lamerd Research Councils for support of this work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mohsen Abbasi.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Abbasi, M. 1,3-Disulfonic acid benzimidazolium chloride as an efficient and recyclable ionic liquid catalyst for the synthesis of 3,4-dihydropyrimidine-2-(1H)-ones/thiones. Res Chem Intermed 42, 3303–3314 (2016). https://doi.org/10.1007/s11164-015-2211-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-015-2211-2

Keywords

Navigation