Research on Chemical Intermediates

, Volume 41, Issue 11, pp 8877–8890 | Cite as

Design of ionic liquid sulfonic acid pyridinium hydrogen sulfate as an efficient, eco-friendly, and reusable catalyst for one-pot synthesis of highly functionalized tetrahydropyridines

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Abstract

Novel ionic liquid sulfonic acid pyridinium hydrogen sulfate ([Pyridine-SO3H]HSO4) is synthesized and characterized by various techniques such as FT-IR, 1H NMR, 13C NMR, TG, DTG, as well as mass spectra. This ionic liquid is used as an efficient, homogeneous, and recyclable catalyst for one-pot synthesis of highly functionalized tetrahydropyridines from the three-component condensation of aromatic aldehydes, ethyl acetoacetate, and substituted anilines under solvent-free conditions. The main advantages of this protocol are the short reaction time, high yields, mild and clean conditions, and several reuse times without noticeably decreasing the catalytic activity.

Keywords

One-pot Sulfonic acid pyridinium hydrogen sulfate Tetrahydropyridines Solvent-free conditions Multicomponent reaction 
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Notes

Acknowledgments

The authors acknowledge Islamic Azad University of Lamerd for support of this work.

References

  1. 1.
    S. Brauch, S.S. Van Berkel, B. Westermann, Chem. Soc. Rev. 42, 4948 (2013)CrossRefGoogle Scholar
  2. 2.
    Y. Gu, Green Chem. 14, 2091 (2012)CrossRefGoogle Scholar
  3. 3.
    M. Shiri, Chem. Rev. 112, 3508 (2012)CrossRefGoogle Scholar
  4. 4.
    S. Duttwyler, C. Lu, B.Q. Mercado, R.G. Bergman, J.A. Ellman, Angew. Chem. Int. Ed. 53, 3877 (2014)CrossRefGoogle Scholar
  5. 5.
    A.T. Khan, M. Lal, M.M. Khan, Tetrahedron Lett. 51, 4419 (2010)CrossRefGoogle Scholar
  6. 6.
    A.R. Mohite, P.R. Sultane, R.G. Bhat, Tetrahedron Lett. 53, 30 (2012)CrossRefGoogle Scholar
  7. 7.
    S. Petit, J.P. Nallet, M. Guillard, J. Dreux, R. Chermat, M. Poncelet, C. Bulach, P. Simon, C. Fontaine, M. Barthelmebs, J.L. Imbs, Eur. J. Med. Chem. 26, 19 (1991)CrossRefGoogle Scholar
  8. 8.
    Y. Zhou, V.E. Gregor, B.K. Ayida, G.C. Winters, Z. Sun, D. Murphy, G. Haley, D. Bailey, J.M. Froelich, S. Fish, Bioorg. Med. Chem. 17, 1206 (2007)CrossRefGoogle Scholar
  9. 9.
    B. Ho, A. Michael, J.P. Crider, Stables. Eur. J. Med. Chem. 36, 265 (2001)CrossRefGoogle Scholar
  10. 10.
    M. Misra, S.K. Pandey, V.P. Pandey, J. Pandey, R. Tripathi, R.P. Tripathi, Bioorg. Med. Chem. 17, 625 (2009)CrossRefGoogle Scholar
  11. 11.
    P.A. Clarke, A.V. Zaytzev, A.C. Whitwood, Tetrahedron Lett. 48, 5209 (2007)CrossRefGoogle Scholar
  12. 12.
    S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Beigbabaei, M. Lashkari, J. Chem. Res. 36, 436 (2012)CrossRefGoogle Scholar
  13. 13.
    S. Mishra, R. Ghosh, Tetrahedron Lett. 52, 2857 (2011)CrossRefGoogle Scholar
  14. 14.
    G. Brahmachari, S. Das, Tetrahedron Lett. 53, 1479 (2012)CrossRefGoogle Scholar
  15. 15.
    S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, A.C. Willis, Res. Chem. Intermed. 40, 723 (2014)CrossRefGoogle Scholar
  16. 16.
    H.J. Wang, L.P. Mo, Z.H. Zhang, ACS. Comb. Sci. 13, 181 (2011)CrossRefGoogle Scholar
  17. 17.
    S. Das, G. Brahmachari, J. Org. Biomol. Chem. 1, 33 (2013)Google Scholar
  18. 18.
    R. Ramachandran, S. Jayanthi, Y.T. Jeong, Tetrahedron 68, 363 (2012)CrossRefGoogle Scholar
  19. 19.
    S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Beigbabaei, A.C. Willis, J. Iran. Chem. Soc. 10, 863 (2013)CrossRefGoogle Scholar
  20. 20.
    A.T. Khan, M.M. Khan, K.K. Bannura, Tetrahedron 66, 7762 (2010)CrossRefGoogle Scholar
  21. 21.
    S. Khaksar, S.M. Vahdat, M. Alipour, C. R. Chim. 16, 1024 (2013)CrossRefGoogle Scholar
  22. 22.
    J. Safaei-Ghomi, A. Ziarati, J. Iran. Chem. Soc. 10, 135 (2013)CrossRefGoogle Scholar
  23. 23.
    M.A.P. Martins, C.P. Frizzo, D.N. Moreira, N. Zanatta, H.G. Bonacorso, Chem. Rev. 108, 2015 (2008)CrossRefGoogle Scholar
  24. 24.
    H. Passos, M.G. Freire, J.A.P. Coutinho, Green Chem. 16, 4786 (2014)CrossRefGoogle Scholar
  25. 25.
    F. Shirini, M. Abedini, M. Seddighi, F. Shaabani-Arbosara, Res. Chem. Intermed. (2014). doi: 10.1007/s11164-014-1852-x Google Scholar
  26. 26.
    J. Safari, Z. Zarnegar, New J. Chem. 38, 358 (2014)CrossRefGoogle Scholar
  27. 27.
    P. Ranjan, B.S. Kitawat, M. Singh, RSC Adv. 4, 53634 (2014)CrossRefGoogle Scholar
  28. 28.
    A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, J. Mol. Liq. 186, 63 (2013)CrossRefGoogle Scholar
  29. 29.
    H. Eshghi, A. Khojastehnezhad, F. Moeinpour, M. Bakavoli, S.M. Seyedi, M. Abbasi, RSC Adv. 4, 39782 (2014)CrossRefGoogle Scholar
  30. 30.
    M. Rahimizadeh, S.M. Seyedi, M. Abbasi, H. Eshghi, A. Khojastehnezhad, F. Moeinpour, M. Bakavoli, J. Iran. Chem. Soc. (2014). doi: 10.1007/s13738-014-0546-z Google Scholar
  31. 31.
    F. Shirini, N.G. Khaligh, J. Mol. Liq. 177, 386 (2013)CrossRefGoogle Scholar
  32. 32.
    T.S. Jin, G. Sun, Y.W. Li, T. Sh Li, Green Chem. 4, 255 (2002)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2015

Authors and Affiliations

  1. 1.Department of Chemistry, Lamerd BranchIslamic Azad UniversityLamerdIran

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