Skip to main content
SpringerLink
Log in

Nanomagnetically modified ferric hydrogen sulfate (NiFe2O4@SiO2-FHS): a reusable green catalyst for the synthesis of highly functionalized piperidine derivatives

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

An efficient and one-pot multi-component procedure for the preparation of functionalized piperidine derivatives from reactions of aromatic aldehydes, substituted anilines and ethyl acetoacetate in the presence of ferric hydrogen sulfate-supported silica-coated magnetic nanoparticles (NiFe2O4@SiO2-FHS) as a magnetically recyclable green catalyst has been developed. The catalysts show environmentally benign character, which can be easily prepared, stored, and recovered several times without obvious significant loss of activity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Scheme 2
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. 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 

  2. Y. Zhou, V.E. Gregor, B.K. Ayida, G.C. Winters, Z. Sun, D. Murphy, G. Haley, D. Bailey, J.M. Froelich, S. Fish, S.E. Webber, T. Hermann, D. Wall, Bioorg. Med. Chem. Lett. 17, 1206 (2007)

    Article  CAS  Google Scholar 

  3. H. Bin, A.M. Crider, J.P. Stables, Eur. J. Med. Chem. 36, 265 (2001)

    Article  Google Scholar 

  4. 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 

  5. J. Esquivias, R.G. Arrayas, J.C. Carretero, J. Am. Chem. Soc. 129, 1480 (2007)

    Article  CAS  Google Scholar 

  6. T.P. Lebold, A.B. Leduc, M.A. Kerr, Org. Lett. 11, 3770 (2009)

    Article  CAS  Google Scholar 

  7. K. Takasu, N. Shindoh, H. Tokuyama, M. Ihara, Tetrahedron 62, 11900 (2006)

    Article  CAS  Google Scholar 

  8. M.S.R. Murty, K.R. Ram, J.S. Yadav, Tetrahedron Lett. 49, 1141 (2008)

    Article  CAS  Google Scholar 

  9. S. Fustero, D. Jimenez, J. Moscardo, S. Catalan, C. Del Pozo, Org. Lett. 9, 5283 (2007)

    Article  CAS  Google Scholar 

  10. F.A. Davis, B. Chao, A. Rao, Org. Lett. 3, 3169 (2001)

    Article  CAS  Google Scholar 

  11. M. Lashkari, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, S.S. Sajadikhah, R. Doostmohamadi, Synth. Commun. 43, 635 (2013)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  13. H.R. Shaterian, K. Azizi, J. Mol. Liq. 180, 187 (2013)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  16. 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 

  17. V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.M. Basset, Chem. Rev. 111, 3036 (2011)

    Article  CAS  Google Scholar 

  18. M.M. Lin, H.H. Kim, H. Kim, M. Muhammed, D.K. Kim, Nano Rev. 1, 4883 (2010)

    Article  Google Scholar 

  19. D. Astruc, F. Lu, J.R. Aranzaes, Angew. Chem. Int. Ed. 44, 7852 (2005)

    Article  CAS  Google Scholar 

  20. A. Hu, G.T. Yee, W. Lin, J. Am. Chem. Soc. 127, 12486 (2005)

    Article  CAS  Google Scholar 

  21. M. Mojtahedi, M.S. Abaee, T. Alishiri, Tetrahedron Lett. 50, 2322 (2009)

    Article  CAS  Google Scholar 

  22. L. Mamani, A. Heydari, M. Sheykhan, Appl. Catal. A Gen. 384, 122 (2010)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  24. A. Khojastehnezhad, F. Moeinpour, A.R. Shams, Synth. React. Inorg. Met. Org. Chem. 42, 273 (2012)

    Article  CAS  Google Scholar 

  25. A. Khojastehnezhad, A. Davoodnia, M. Bakavoli, N. Tavakoli-Hoseini, M. Zeinali-Dastmalbaf, Chin. J. Chem. 29, 297 (2011)

    Article  CAS  Google Scholar 

  26. A. Davoodnia, A. Khojastehnezhad, N. Tavakoli-Hoseini, Bull. Korean Chem. Soc. 32, 2243 (2011)

    Article  CAS  Google Scholar 

  27. A. Khojastehnezhad, M. Rahimizadeh, H. Eshghi, F. Moeinpour, M. Bakavoli, Chin. J. Cat. 35, 376 (2014)

    Article  CAS  Google Scholar 

  28. A. Khojastehnezhad, M. Rahimizadeh, F. Moeinpour, H. Eshghi, M. Bakavoli, C. R. Chim. (2013). doi:10.1016/j.crci.2013.07.013

    Google Scholar 

  29. D. Zins, V. Cabuil, R. Massart, J. Mol. Liq. 83, 217 (1999)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  31. R. Ghorbani-Vaghei, H. Shahbazi, C. R. Chim. 16, 1047 (2013)

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  33. H. Eshghi, M. Rahimizadeh, Z. Bakhtiarpoor, M. Pordel, Chin. Chem. Lett. 23, 673 (2012)

    Article  CAS  Google Scholar 

  34. H. Eshghi, S.M. Seyedi, E. Safaei, M. Vakili, A. Farhadipour, M. Bayat-Mokhtari, J. Mol. Catal. A: Chem. 363, 430 (2012)

    Article  Google Scholar 

  35. J. Aboonajmi, M.R. Mousavi, M.T. Maghsoodlou, N. Hazeri, A. Masoumnia, Res. Chem. Intermed. (2013). doi:10.1007/s11164-013-1320-z

    Google Scholar 

Download references

Acknowledgments

The authors are grateful to Ferdowsi University of Mashhad for financial support.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, Mashhad, Iran

    Mohammad Rahimizadeh, Seyed Mohammad Seyedi, Mohsen Abbasi, Hossein Eshghi & Mehdi Bakavoli

  2. Department of Chemistry, College of Sciences, Mashhad Branch, Islamic Azad University, Mashhad, Iran

    Amir Khojastehnezhad

  3. Department of Chemistry, College of Sciences, Bandar Abbas Branch, Islamic Azad University, 7915893144, Bandar Abbas, Iran

    Farid Moeinpour

Authors
  1. Mohammad Rahimizadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Seyed Mohammad Seyedi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mohsen Abbasi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hossein Eshghi
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Amir Khojastehnezhad
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Farid Moeinpour
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Mehdi Bakavoli
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Amir Khojastehnezhad.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rahimizadeh, M., Seyedi, S.M., Abbasi, M. et al. Nanomagnetically modified ferric hydrogen sulfate (NiFe2O4@SiO2-FHS): a reusable green catalyst for the synthesis of highly functionalized piperidine derivatives. J IRAN CHEM SOC 12, 839–844 (2015). https://doi.org/10.1007/s13738-014-0546-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-014-0546-z

Keywords

Search

Navigation