Skip to main content
Log in

1, 3-Disulfonic acid imidazolium hydrogen sulphate as an efficient and reusable ionic liquid for the multicomponent synthesis of polyhydroquinoline derivatives under solvent-free conditions

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

Abstract

A facile and highly effective one-pot synthesis of polyhydroquinoline derivatives is reported via Hantzsch condensation of aldehydes, 1,3-dicarbonyl compounds, ethyl acetoacetate, and ammonium acetate in the presence of 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient and recyclable ionic liquid under solvent-free conditions. This methodology offers several advantages such as short reaction times, high yields, environmentally benign, mild reaction conditions, simple work-up procedure, and reusability of the ionic liquid.

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
Scheme 2

Similar content being viewed by others

References

  1. G. Guillena, D.J. Ramon, M. Yus, Tetrahedron Asymmetry 18, 693 (2007)

    Article  CAS  Google Scholar 

  2. A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)

    Article  CAS  Google Scholar 

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

    Google Scholar 

  4. I. Ugi, Pure Appl. Chem. 73, 187 (2001)

    Article  CAS  Google Scholar 

  5. C.C.A. Cariou, G.J. Clarkson, M. Shipman, J. Org. Chem. 73, 9762 (2008)

    Article  CAS  Google Scholar 

  6. L. Yu, B. Chen, X. Huang, Tetrahedron Lett. 48, 925 (2007)

    Article  Google Scholar 

  7. P.N. Kalaria, S.P. Satasia, D.K. Raval, Eur. J. Med. Chem. 78, 207 (2014)

    Article  CAS  Google Scholar 

  8. S.C. Karad, V.B. Purohit, D.K. Raval, P.N. Kalaria, J.R. Avalani, P. Thakor, V.R. Thakkar, RSC Adv. 5, 16000 (2015)

    Article  CAS  Google Scholar 

  9. P.P. Mager, R.A. Coburn, A.J. Solo, D.J. Triggle, H. Rothe, Drug Des. Discov. 8, 273 (1992)

    CAS  Google Scholar 

  10. A. Sausins, G. Duburs, Heterocycles 27, 269 (1988)

    Article  CAS  Google Scholar 

  11. R. Manmhold, B. Jablonka, W. Voigdt, K. Schoenafinger, E. Schraven, J. Med. Chem. 27, 229 (1992)

    Article  Google Scholar 

  12. A.C. Gaudio, A. Korokovas, Y. Takahata, J. Pharm. Sci. 83, 1110 (1994)

    Article  CAS  Google Scholar 

  13. D.J. Triggle, in Comprehensive Medicinal Chemistry, vol. II, ed. by J.C. Emmet (Pergamon, Oxford, 1990)

    Google Scholar 

  14. V. Klusa, Drugs Future 20, 135 (1995)

    Article  Google Scholar 

  15. R.G. Bretzel, C.C. Bollen, E. Maeser, K.F. Federlin, Am. J. Kidney Dis. 21, 53 (1993)

    Article  CAS  Google Scholar 

  16. R.G. Bretzel, C.C. Bollen, E. Maeser, Drugs Future 17, 465 (1992)

    Article  Google Scholar 

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

    Google Scholar 

  18. Z. Zarnegar, J. Safari, Z. Mansouri, Kafroudi. Catal. Commun. 59, 216 (2015)

    Article  CAS  Google Scholar 

  19. V.K. Ahluwalia, B. Goyal, U. Das, J. Chem. Res. (s) 7, 266 (1997)

  20. S. Margarita, O. Estael, V. Yamila, P. Beatriz, M. Lourdes, M. Nazario, Q. Margarita, S. Carlos, L.S. Jose, N. Hector, B. Norbert, M.P. Oswald, Tetrahedron 55, 875 (1999)

    Article  Google Scholar 

  21. A. Hantzsch, Ann. Chem. 1, 215 (1882)

    Google Scholar 

  22. G. Sabitha, G.S.K.K. Reddy, C.S. Reddy, J.S. Yadav, Tetrahedron Lett. 44, 4129 (2003)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  24. A. Dondoni, A. Massi, E. Minghini, V. Bertolasi, Tetrahedron 60, 2311 (2004)

    Article  CAS  Google Scholar 

  25. L.M. Wang, J. Sheng, L. Zhang, J.W. Han, Z. Fan, H. Tian, C.T. Qian, Tetrahedron 61, 1539 (2005)

    Article  CAS  Google Scholar 

  26. M. Maheswara, V. Siddaiah, G.L. Damu, C.V. Rao, ARKIVOC ii, 201 (2006)

    Google Scholar 

  27. M.M. Heravi, K. Bakhtiri, N.M. Javadi, F.F. Bamoharram, M. Saeedi, H.A. Oskooi, J. Mol. Catal. A Chem. 264, 50 (2007)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  29. S.R. Cherkupally, R. Mekala, Chem. Pharm. Bull. 56, 1002 (2008)

    Article  CAS  Google Scholar 

  30. G. Babu, P.T. Perumal, Aldrichimica Acta 33, 16 (2000)

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  32. F. Shirini, S.V. Atghia, M.A. Khoshdel, Iran. J. Catal. 1, 93 (2011)

    CAS  Google Scholar 

  33. A. Kumar, R.A. Maurya, Tetrahedron Lett. 48, 3887 (2007)

    Article  CAS  Google Scholar 

  34. S. Kumar, P. Sharma, K.K. Kapoor, M.S. Hundal, Tetrahedron 64, 536 (2008)

    Article  CAS  Google Scholar 

  35. J.B. Sainani, A.C. Shah, V.P. Aray, Indian J. Chem. 33B, 526 (1994)

    CAS  Google Scholar 

  36. N.K. Ladani, D.C. Mungra, M.P. Patel, R.G. Patel, Chin. Chem. Lett. 22, 1407 (2011)

    Article  CAS  Google Scholar 

  37. A. Kumar, R.A. Maurya, Synlett 6, 883 (2008)

    Article  Google Scholar 

  38. P.T. Anastas, J.C. Warner, Green Chemistry: Theory and Practice (Oxford University Press, Oxford, 1998)

    Google Scholar 

  39. M. Poliakoff, M.J. Fitzpatric, T.R. Farren, P.T. Anastas, Green Chemistry: Science and Politics of change. Science 297, 807 (2002)

    Article  CAS  Google Scholar 

  40. I.T. Horváth, P.T. Anastas, Innovations and green chemistry. Chem. Rev. 107, 2169 (2007)

    Article  Google Scholar 

  41. Z. Chen, Q. Zhu, W. Su, Tetrahedron Lett. 52, 2601 (2011)

    Article  CAS  Google Scholar 

  42. H.G.O. Alvim, G.A. Bataglion, L.M. Ramos, A.L. de Oliveira, H.C.B. de Oliveira, M.N. Eberlin, J.L. de Macedo, W.A. da Silva, B.A.D. Neto, Tetrahedron 70, 3306 (2014)

    Article  CAS  Google Scholar 

  43. H.G.O. Alvim, T.B. de Lima, H.C.B. de Oliveira, F.C. Gozzo, J.L. de Macedo, P.V. Abdelnur, W.A. Silva, B.A.D. Neto, ACS Catal. 3, 1420 (2013)

    Article  CAS  Google Scholar 

  44. R. Fu, Y. Yang, W. Lai, Y. Ma, Z. Chen, J. Zhou, W. Chai, Q. Wang, R. Yuan, Synth. Commun. 45, 467 (2015)

    Article  CAS  Google Scholar 

  45. J. Akbari, A. Heydari, H.R. Kalhor, S.A. Kohan, J. Comb. Chem. 12, 137 (2010)

    Article  CAS  Google Scholar 

  46. F. Shirini, N.G. Khaligh, S. Akbari-Dadamahaleh, J. Mol. Catal. A Chem. 365, 15 (2012)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  48. F. Shirini, A. Yahyazadeh, K. Mohammadi, Chin. Chem. Lett. 25, 341 (2014)

    Article  CAS  Google Scholar 

  49. M. Tajbakhsh, H. Alinezhad, M. Norouzi, S. Baghery, M. Akbari, J. Mol. Liq. 177, 44 (2013)

    Article  CAS  Google Scholar 

  50. M. Nasr-Esfahani, T. Abdizadeh, Orient. J. Chem. 28, 1249 (2012)

    Article  CAS  Google Scholar 

  51. X.L. Zhang, S.R. Sheng, X.L. Liu, X.L. Liu, ARKIVOC xiii, 79 (2007)

    Google Scholar 

  52. M. Hong, C. Cai, W.B. Yi, J. Fluorine Chem. 131, 111 (2010)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  54. A. Davoodnia, M. Khashi, N. Tavakoli-Hoseini, Chin. J. Catal. 34, 1173 (2013)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors acknowledge financial support for this work from the Iran National Science Foundation (INSF) (Grant Number 93014856) and partial support of this work by the Research Council of the University of Guilan. F. Shirini and K. Mohammadi also wish to thank the Sobhandarou Company for the partial facilities.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Farhad Shirini or Asieh Yahyazadeh.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mohammadi, K., Shirini, F. & Yahyazadeh, A. 1, 3-Disulfonic acid imidazolium hydrogen sulphate as an efficient and reusable ionic liquid for the multicomponent synthesis of polyhydroquinoline derivatives under solvent-free conditions. Res Chem Intermed 42, 2047–2054 (2016). https://doi.org/10.1007/s11164-015-2134-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-015-2134-y

Keywords

Navigation