Advertisement

Research on Chemical Intermediates

, Volume 44, Issue 10, pp 5893–5910 | Cite as

Fabrication, identification and application of Fe3O4 bonded nicotinic acid-sulfonic acid chloride as a retrievable magnetic nanostructured catalyst for the one-pot synthesis of 1-carbamato-alkyl-2-naphthols

  • Ardeshir Khazaei
  • Mahsa Tavasoli
  • Ahmad Reza Moosavi-Zare
Article

Abstract

In the presented work, Fe3O4 bonded nicotinic acid-sulfonic acid chloride (Fe3O4@nicotinic acid @sulfonic acid chloride), as a magnetic reusable catalyst, was prepared by a simple procedure. The identification of Fe3O4@nicotinic acid @sulfonic acid chloride was studied by Fourier transform infrared spectroscopy, X-ray diffraction, thermal gravimetric analysis, scanning electron microscopy, energy dispersive X-ray analysis and vibrating sample magnetometry. Fe3O4@nicotinic acid @sulfonic acid chloride was employed as an efficient and heterogeneous catalyst for the one-pot synthesis of some 1-carbamato-alkyl-2-naphthol derivatives in high yields under solvent-free conditions. Simple work up, high yields, short reaction times and easy recovery of catalyst are some advantages of this work.

Graphical Abstract

Keywords

Fe3O4@nicotinic acid @sulfonic acid chloride Fe3O4 nanoparticle 1-Carbamato-alkyl-2-naphthol Solvent-free 

Notes

Acknowledgements

We thank Bu-Ali Sina University and Iran National Science Foundation (INSF) for financial support given to our research groups.

Supplementary material

11164_2018_3462_MOESM1_ESM.docx (2.4 mb)
Supplementary material 1 (DOCX 2411 kb)

References

  1. 1.
    D. Astruc, F. Lu, J.R. Aranzaes, Angew. Chem. Int. Ed. 44, 7852 (2005)CrossRefGoogle Scholar
  2. 2.
    D. Astruc, Nanoparticles and Catalysis (Wiley, Weinheim, 2008)Google Scholar
  3. 3.
    G.A. Somorjai, H. Frei, J.Y. Park, J. Am. Chem. Soc. 131, 16589 (2009)CrossRefGoogle Scholar
  4. 4.
    A. Taher, J.B. Kim, J.Y. Jung, W.S. Ahn, M.J. Jin, Synlett 15, 2477 (2009)Google Scholar
  5. 5.
    Q. Zhang, H. Su, J. Luo, Y. Wei, Green Chem. 14, 201 (2012)CrossRefGoogle Scholar
  6. 6.
    L. Lin, C. Zou, J. Chem. Eng. Data 62, 762 (2017)CrossRefGoogle Scholar
  7. 7.
    M.A. Zolfigol, A.R. Moosavi-Zare, P. Moosavi, V. Khakyzadeh, A. Zare, C. R. Chimie 16, 962 (2013)CrossRefGoogle Scholar
  8. 8.
    M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, A. Rostami, A. Zare, N. Iranpoor, M.H. Beyzavi, R. Luque, Green Chem. 15, 2132 (2013)CrossRefGoogle Scholar
  9. 9.
    M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, A. Zare, P. Arghavani-Hadi, Z. Mohammadi, M.H. Beyzavi, S. Afr, J. Chem. 65, 280 (2012)Google Scholar
  10. 10.
    A. Khazaei, A.R. Moosavi-Zare, H. Afshar-Hezarkhania, V. Khakyzadeh, RSC Adv. 4, 32142 (2014)CrossRefGoogle Scholar
  11. 11.
    A. Khazaei, F. Gholami, V. Khakyzadeh, A.R. Moosavi-Zare, J. Afsar, RSC Adv. 5, 14305 (2015)CrossRefGoogle Scholar
  12. 12.
    A. Khazaei, A. Ranjbaran, F. Abbasi, M. Khazaei, A.R. Moosavi-Zare, RSC Adv. 5, 13643 (2015)CrossRefGoogle Scholar
  13. 13.
    A. Khazaei, M.A. Zolfigol, F. Karimitabar, I. Nikokar, A.R. Moosavi-Zare, RSC Adv. 5, 71402 (2015)CrossRefGoogle Scholar
  14. 14.
    A. Khazaei, F. Abbasi, A.R. Moosavi-Zare, New J. Chem. 38, 5287 (2014)CrossRefGoogle Scholar
  15. 15.
    A.R. Moosavi-Zare, M.A. Zolfigol, M. Daraei, Synlett 25, 1173 (2014)CrossRefGoogle Scholar
  16. 16.
    A.R. Moosavi-Zare, M.A. Zolfigol, S. Farahmand, A. Zare, A.R. Pourali, R. Ayazi-Nasrabadi, Synlett 25, 193 (2014)CrossRefGoogle Scholar
  17. 17.
    H.R. Shaterian, H. Yarahmadi, M. Ghashang, Bioorg. Med. Chem. Lett. 18, 788 (2008)CrossRefPubMedGoogle Scholar
  18. 18.
    A.Y. Shen, C.T. Tsai, C.L. Chen, Eur. J. Med. Chem. 34, 877 (1999)CrossRefGoogle Scholar
  19. 19.
    Z. Song, X. Sun, L. Liu, Y. Cui, Res. Chem. Intermed. 39, 2123 (2012)CrossRefGoogle Scholar
  20. 20.
    D. Kundu, A. Majee, A. Hajra, Catal. Comm. 11, 1157 (2010)CrossRefGoogle Scholar
  21. 21.
    N. Tavakoli-Hoseini, M.M. Heravi, F.F. Bamoharran, A. Davoodnia, Bull. Korean Chem. Soc. 32, 787 (2011)CrossRefGoogle Scholar
  22. 22.
    H.R. Shaterian, A. Hosseinian, M. Ghashang, Tetrahedron Lett. 49, 5804 (2008)CrossRefGoogle Scholar
  23. 23.
    M. Wang, Q. Wang, S. Zhao, X. Wan, Monatsh. Chem. 144, 975 (2013)CrossRefGoogle Scholar
  24. 24.
    A. Khazaei, F. Abbasi, A.R. Moosavi-Zare, RSC Adv. 4, 1388 (2014)CrossRefGoogle Scholar
  25. 25.
    M.R. Mohammad Shafiee, R. Moloudi, M. Ghashang, J. Chem. Res. 35, 622 (2011)CrossRefGoogle Scholar
  26. 26.
    J.M. Yang, ChN Jiang, H. Dong, D. Fang, J. Chem. Res. 37, 257 (2013)CrossRefGoogle Scholar
  27. 27.
    H.R. Shaterian, A. Hosseinian, Res. Chem. Intermed. 40, 3011 (2014)CrossRefGoogle Scholar
  28. 28.
    A. Zare, T. Yousofi, A.R. Moosavi-Zare, RSC Adv. 2, 7988 (2012)CrossRefGoogle Scholar
  29. 29.
    M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Appl. Catal. A 400, 70 (2011)CrossRefGoogle Scholar
  30. 30.
    A. Ghorbani-Choghamarani, G. Azadi, RSC Adv. 5, 9752 (2015)CrossRefGoogle Scholar
  31. 31.
    Y.T. Tao, J. Am. Chem. Soc. 115, 4350 (1993)CrossRefGoogle Scholar
  32. 32.
    K.V.P.M. Shafi, A. Ulman, X.Z. Yan, N.L. Yang, C. Estournes, H. White, Rafailovich M. Langmuir 17, 5093 (2001)CrossRefGoogle Scholar
  33. 33.
    A. Khazaei, F. Abbasi, A.R. Moosavi-Zare, J. Sulfur Chem. 36, 364 (2015)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V., part of Springer Nature 2018

Authors and Affiliations

  • Ardeshir Khazaei
    • 1
  • Mahsa Tavasoli
    • 1
  • Ahmad Reza Moosavi-Zare
    • 2
  1. 1.Faculty of ChemistryBu-Ali Sina UniversityHamedanIran
  2. 2.Department of ChemistrySayyed Jamaleddin Asadabadi UniversityAsadabadIran

Personalised recommendations