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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.

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References

  1. S. Brauch, S.S. Van Berkel, B. Westermann, Chem. Soc. Rev. 42, 4948 (2013)

    Article  CAS  Google Scholar 

  2. Y. Gu, Green Chem. 14, 2091 (2012)

    Article  CAS  Google Scholar 

  3. M. Shiri, Chem. Rev. 112, 3508 (2012)

    Article  CAS  Google Scholar 

  4. S. Duttwyler, C. Lu, B.Q. Mercado, R.G. Bergman, J.A. Ellman, Angew. Chem. Int. Ed. 53, 3877 (2014)

    Article  CAS  Google Scholar 

  5. A.T. Khan, M. Lal, M.M. Khan, Tetrahedron Lett. 51, 4419 (2010)

    Article  CAS  Google Scholar 

  6. A.R. Mohite, P.R. Sultane, R.G. Bhat, Tetrahedron Lett. 53, 30 (2012)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  9. B. Ho, A. Michael, J.P. Crider, Stables. Eur. J. Med. Chem. 36, 265 (2001)

    Article  CAS  Google Scholar 

  10. M. Misra, S.K. Pandey, V.P. Pandey, J. Pandey, R. Tripathi, R.P. Tripathi, Bioorg. Med. Chem. 17, 625 (2009)

    Article  CAS  Google Scholar 

  11. P.A. Clarke, A.V. Zaytzev, A.C. Whitwood, Tetrahedron Lett. 48, 5209 (2007)

    Article  CAS  Google Scholar 

  12. S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Beigbabaei, M. Lashkari, J. Chem. Res. 36, 436 (2012)

    Article  Google Scholar 

  13. S. Mishra, R. Ghosh, Tetrahedron Lett. 52, 2857 (2011)

    Article  CAS  Google Scholar 

  14. G. Brahmachari, S. Das, Tetrahedron Lett. 53, 1479 (2012)

    Article  CAS  Google Scholar 

  15. S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, A.C. Willis, Res. Chem. Intermed. 40, 723 (2014)

    Article  CAS  Google Scholar 

  16. H.J. Wang, L.P. Mo, Z.H. Zhang, ACS. Comb. Sci. 13, 181 (2011)

    Article  CAS  Google Scholar 

  17. S. Das, G. Brahmachari, J. Org. Biomol. Chem. 1, 33 (2013)

    Google Scholar 

  18. R. Ramachandran, S. Jayanthi, Y.T. Jeong, Tetrahedron 68, 363 (2012)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  20. A.T. Khan, M.M. Khan, K.K. Bannura, Tetrahedron 66, 7762 (2010)

    Article  CAS  Google Scholar 

  21. S. Khaksar, S.M. Vahdat, M. Alipour, C. R. Chim. 16, 1024 (2013)

    Article  CAS  Google Scholar 

  22. J. Safaei-Ghomi, A. Ziarati, J. Iran. Chem. Soc. 10, 135 (2013)

    Article  CAS  Google Scholar 

  23. M.A.P. Martins, C.P. Frizzo, D.N. Moreira, N. Zanatta, H.G. Bonacorso, Chem. Rev. 108, 2015 (2008)

    Article  CAS  Google Scholar 

  24. H. Passos, M.G. Freire, J.A.P. Coutinho, Green Chem. 16, 4786 (2014)

    Article  CAS  Google Scholar 

  25. F. Shirini, M. Abedini, M. Seddighi, F. Shaabani-Arbosara, Res. Chem. Intermed. (2014). doi:10.1007/s11164-014-1852-x

    Google Scholar 

  26. J. Safari, Z. Zarnegar, New J. Chem. 38, 358 (2014)

    Article  CAS  Google Scholar 

  27. P. Ranjan, B.S. Kitawat, M. Singh, RSC Adv. 4, 53634 (2014)

    Article  CAS  Google Scholar 

  28. A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, J. Mol. Liq. 186, 63 (2013)

    Article  CAS  Google Scholar 

  29. H. Eshghi, A. Khojastehnezhad, F. Moeinpour, M. Bakavoli, S.M. Seyedi, M. Abbasi, RSC Adv. 4, 39782 (2014)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  32. T.S. Jin, G. Sun, Y.W. Li, T. Sh Li, Green Chem. 4, 255 (2002)

    Article  CAS  Google Scholar 

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Acknowledgments

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

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Authors and Affiliations

  1. Department of Chemistry, Lamerd Branch, Islamic Azad University, Lamerd, Fars, Iran

    Sedigheh Mohammadi & Mohsen Abbasi

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  1. Sedigheh Mohammadi
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  2. Mohsen Abbasi
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Correspondence to Mohsen Abbasi.

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Mohammadi, S., Abbasi, M. 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. Res Chem Intermed 41, 8877–8890 (2015). https://doi.org/10.1007/s11164-015-1934-4

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  • DOI: https://doi.org/10.1007/s11164-015-1934-4

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