Skip to main content
Log in

Polyhydroquinolines: 1-sulfopyridinium chloride catalyzed an efficient one-pot multicomponent synthesis via Hantzsch condensation under solvent-free conditions

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

Abstract

A simple and highly efficient method has been developed for the construction of polyhydroquinoline derivatives via one-pot, four-component Hantzsch condensation of various aldehydes, dimedone, ethyl acetoacetate, and ammonium acetate in the presence of an ionic liquid, 1-sulpopyridinium chloride, as a catalyst under solvent-free conditions. This methodology has an advantage of high yields, short reaction times, a clean reaction profile, and reusability of the catalyst.

Graphical Abstract

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.

Fig. 1
Scheme 1
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. B.H. Rotstein, S. Zaretsky, V. Rai, A.K. Yudin, Chem. Rev. 114, 8323 (2014)

    Article  CAS  Google Scholar 

  2. A. Domling, W. Wang, K. Wang, Chem. Rev. 112, 3083 (2012)

    Article  CAS  Google Scholar 

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

    Book  Google Scholar 

  4. J.E. Martyn, R.S. Kenneth, Pure Appl. Chem. 72, 1391 (2000)

    Google Scholar 

  5. Q. Zhang, S. Zhang, Y. Deng, Green Chem. 13, 2619 (2011)

    Article  CAS  Google Scholar 

  6. K. Tanaka, F. Toda, Chem. Rev. 100, 1025 (2000)

    Article  CAS  Google Scholar 

  7. M.S. Singh, S. Chowdhury, RSC Adv. 2, 4547 (2012)

    Article  CAS  Google Scholar 

  8. J.L. Reid, P.A. Meredith, F. Pasanisi, J. Cardiovasc. Pharmacol. 7, S18 (1985)

    Article  Google Scholar 

  9. R.H. Bocker, F.P. Guengerich, J. Med. Chem. 29, 1596 (1986)

    Article  CAS  Google Scholar 

  10. F. Bossert, H. Meyer, E. Wehinger, Angew. Chem. Int. Ed. Engl. 20, 762 (1981)

    Article  Google Scholar 

  11. D.J. Triggle, D.A. Langs, R.A. Janis, Med. Res. Rev. 9, 123 (1989)

    Article  CAS  Google Scholar 

  12. A. Hilgeroth, Mini-Rev. Med. Chem. 2, 235 (2002)

    Article  CAS  Google Scholar 

  13. H.S. Chung, W.S. Woo, J. Nat. Prod. 64, 1579 (2001)

    Article  CAS  Google Scholar 

  14. M. Kawase, A. Shah, H. Gaveriya, N. Motohashi, H. Sakagami, A. Varga, J. Molnar, Bioorg. Med. Chem. 10, 1051 (2002)

    Article  CAS  Google Scholar 

  15. O.A. El-Sayed, T.M. Al-Turki, H.M. Al-Daffiri, B.A. Al-Bassam, M.E. Hussein, Boll. Chim. Farm. 143, 227 (2004)

    CAS  Google Scholar 

  16. A. Ryckebusch, R. Derprez-Poulain, L. Maes, M.A. Debreu-Fontaine, E. Mouray, P. Grellier, C. Sergheraert, J. Med. Chem. 46, 542 (2003)

    Article  CAS  Google Scholar 

  17. M.Q. Zhang, A. Haemers, D. Vanden Berghe, S.R. Pattyn, W. Bollaert, I. Levshin, J. Heterocycl. Chem. 28, 673 (1991)

    Article  CAS  Google Scholar 

  18. H. Gevariya, B. Desai, V. Vora, A. Shah, Heterocycl. Commun. 7, 481 (2011)

    Google Scholar 

  19. M. Rueping, A.P. Antonchick, T. Theissmann, Angew. Chem. Int. Ed. 45, 3683 (2006)

    Article  CAS  Google Scholar 

  20. R. Boer, V. Gekeler, Drugs Future 20, 499 (1995)

    Google Scholar 

  21. B. Love, K.M. Sander, J. Org. Chem. 30, 1914 (1965)

    Article  Google Scholar 

  22. A. Hantzsch, Ber. Dtsch. Chem. Ges. 21, 942 (1888)

    Article  Google Scholar 

  23. A. Hantzsch, Ber. Dtsch. Chem. Ges. 23, 1747 (1890)

    Google Scholar 

  24. J.B. Sainani, A.C. Shah, Indian J. Chem. Sect. B 33, 526 (1994)

    Google Scholar 

  25. S.J. Tu, J.F. Zhou, X. Deng, P.J. Cai, H. Wang, J.C. Feng, Chin. J. Org. Chem. 21, 313 (2001)

    CAS  Google Scholar 

  26. A. Maquestiau, A. Mayence, J.J. Vanden Eynde, Tetrahedron Lett. 32, 3839 (1991)

    Article  CAS  Google Scholar 

  27. S.J. Ji, Z.Q. Jiang, J. Lu, T.P. Loh, Synlett 5, 831 (2004)

    Article  Google Scholar 

  28. N.N. Karade, V.H. Budhewar, S.V. Shinde, W.N. Jadhav, Lett. Org. Chem. 4, 16 (2007)

    Article  CAS  Google Scholar 

  29. M. Nasr-Esfahani, S.J. Hoseini, M. Montazerozohori, R. Mehrabi, H. Nasrabadi, J. Mol. Catal. A Chem. 382, 99 (2014)

    Article  CAS  Google Scholar 

  30. S. Ko, M.N.V. Sastry, C. Linc, C.F. Yao, Tetrahedron Lett. 46, 5771 (2005)

    Article  CAS  Google Scholar 

  31. J.L. Donelson, R.A. Gibbs, S.K. De, J. Mol. Catal. A Chem. 256, 309 (2006)

    Article  CAS  Google Scholar 

  32. M. Maheswara, V. Siddaiah, G.L.V. Damu, C.V. Rao, Arkivoc 2, 201 (2006)

    Google Scholar 

  33. A. Khojastehnezhad, F. Moeinpour, A. Davoodnia, Chin. Chem. Lett. 22, 807 (2011)

    Article  CAS  Google Scholar 

  34. S. Ko, C.F. Yao, Tetrahedron 62, 7293 (2006)

    Article  CAS  Google Scholar 

  35. R. Surasani, D. Kalita, A.V.D. Rao, K. Yarbagi, K.B. Chandrasekhar, J. Fluor. Chem. 135, 91 (2012)

    Article  CAS  Google Scholar 

  36. C.S. Reddy, M. Raghu, Chin. Chem. Lett. 19, 775 (2008)

    Article  CAS  Google Scholar 

  37. B. Janardhan, B. Rajitha, P.A. Crooks, J. Saudi Chem. Soc. 18, 722 (2014)

    Article  Google Scholar 

  38. J. Safari, S.H. Banitaba, S.D. Khalili, J. Mol. Catal. A Chem. 335, 46 (2011)

    Article  CAS  Google Scholar 

  39. M. Behrooz, T. Reza, S. Zeinalabedin, K. Mina, Acta Chim. Slov. 59, 814 (2012)

    Google Scholar 

  40. M. Behrooz, T. Reza, K. Mina, S.A. Samaneh, J. Mex. Chem. Soc. 57, 290 (2013)

    Google Scholar 

  41. B. Sakram, B. Sonyanaik, K. Ashok, S. Rambabu, S.K. Johnmiya, Res. Chem. Intermed. 42, 1699 (2016)

    Article  CAS  Google Scholar 

  42. A.R.M. Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, A. Hasaninejad, Appl. Catal. A Gen. 467, 61 (2013)

    Article  Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge the head of the Department of Chemistry, Osmania University, for providing research facilities. One of the authors (B. Sonyanaik) thanks the University Grant Commission (UGC) New Delhi, India, for providing research fellowships.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to B. Sakram.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1519 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sakram, B., Sonyanaik, B., Ashok, K. et al. Polyhydroquinolines: 1-sulfopyridinium chloride catalyzed an efficient one-pot multicomponent synthesis via Hantzsch condensation under solvent-free conditions. Res Chem Intermed 42, 7651–7658 (2016). https://doi.org/10.1007/s11164-016-2559-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-016-2559-y

Keywords

Navigation