Skip to main content
SpringerLink
Log in

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

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

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

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
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Scheme 3
Fig. 7
Fig. 8

Similar content being viewed by others

References

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

    Article  CAS  Google Scholar 

  2. D. Astruc, Nanoparticles and Catalysis (Wiley, Weinheim, 2008)

    Google Scholar 

  3. G.A. Somorjai, H. Frei, J.Y. Park, J. Am. Chem. Soc. 131, 16589 (2009)

    Article  CAS  Google Scholar 

  4. A. Taher, J.B. Kim, J.Y. Jung, W.S. Ahn, M.J. Jin, Synlett 15, 2477 (2009)

    Google Scholar 

  5. Q. Zhang, H. Su, J. Luo, Y. Wei, Green Chem. 14, 201 (2012)

    Article  CAS  Google Scholar 

  6. L. Lin, C. Zou, J. Chem. Eng. Data 62, 762 (2017)

    Article  CAS  Google Scholar 

  7. M.A. Zolfigol, A.R. Moosavi-Zare, P. Moosavi, V. Khakyzadeh, A. Zare, C. R. Chimie 16, 962 (2013)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    CAS  Google Scholar 

  10. A. Khazaei, A.R. Moosavi-Zare, H. Afshar-Hezarkhania, V. Khakyzadeh, RSC Adv. 4, 32142 (2014)

    Article  CAS  Google Scholar 

  11. A. Khazaei, F. Gholami, V. Khakyzadeh, A.R. Moosavi-Zare, J. Afsar, RSC Adv. 5, 14305 (2015)

    Article  CAS  Google Scholar 

  12. A. Khazaei, A. Ranjbaran, F. Abbasi, M. Khazaei, A.R. Moosavi-Zare, RSC Adv. 5, 13643 (2015)

    Article  CAS  Google Scholar 

  13. A. Khazaei, M.A. Zolfigol, F. Karimitabar, I. Nikokar, A.R. Moosavi-Zare, RSC Adv. 5, 71402 (2015)

    Article  CAS  Google Scholar 

  14. A. Khazaei, F. Abbasi, A.R. Moosavi-Zare, New J. Chem. 38, 5287 (2014)

    Article  CAS  Google Scholar 

  15. A.R. Moosavi-Zare, M.A. Zolfigol, M. Daraei, Synlett 25, 1173 (2014)

    Article  Google Scholar 

  16. A.R. Moosavi-Zare, M.A. Zolfigol, S. Farahmand, A. Zare, A.R. Pourali, R. Ayazi-Nasrabadi, Synlett 25, 193 (2014)

    Article  CAS  Google Scholar 

  17. H.R. Shaterian, H. Yarahmadi, M. Ghashang, Bioorg. Med. Chem. Lett. 18, 788 (2008)

    Article  CAS  PubMed  Google Scholar 

  18. A.Y. Shen, C.T. Tsai, C.L. Chen, Eur. J. Med. Chem. 34, 877 (1999)

    Article  CAS  Google Scholar 

  19. Z. Song, X. Sun, L. Liu, Y. Cui, Res. Chem. Intermed. 39, 2123 (2012)

    Article  Google Scholar 

  20. D. Kundu, A. Majee, A. Hajra, Catal. Comm. 11, 1157 (2010)

    Article  CAS  Google Scholar 

  21. N. Tavakoli-Hoseini, M.M. Heravi, F.F. Bamoharran, A. Davoodnia, Bull. Korean Chem. Soc. 32, 787 (2011)

    Article  CAS  Google Scholar 

  22. H.R. Shaterian, A. Hosseinian, M. Ghashang, Tetrahedron Lett. 49, 5804 (2008)

    Article  CAS  Google Scholar 

  23. M. Wang, Q. Wang, S. Zhao, X. Wan, Monatsh. Chem. 144, 975 (2013)

    Article  CAS  Google Scholar 

  24. A. Khazaei, F. Abbasi, A.R. Moosavi-Zare, RSC Adv. 4, 1388 (2014)

    Article  CAS  Google Scholar 

  25. M.R. Mohammad Shafiee, R. Moloudi, M. Ghashang, J. Chem. Res. 35, 622 (2011)

    Article  Google Scholar 

  26. J.M. Yang, ChN Jiang, H. Dong, D. Fang, J. Chem. Res. 37, 257 (2013)

    Article  Google Scholar 

  27. H.R. Shaterian, A. Hosseinian, Res. Chem. Intermed. 40, 3011 (2014)

    Article  CAS  Google Scholar 

  28. A. Zare, T. Yousofi, A.R. Moosavi-Zare, RSC Adv. 2, 7988 (2012)

    Article  CAS  Google Scholar 

  29. M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Appl. Catal. A 400, 70 (2011)

    Article  CAS  Google Scholar 

  30. A. Ghorbani-Choghamarani, G. Azadi, RSC Adv. 5, 9752 (2015)

    Article  CAS  Google Scholar 

  31. Y.T. Tao, J. Am. Chem. Soc. 115, 4350 (1993)

    Article  CAS  Google Scholar 

  32. K.V.P.M. Shafi, A. Ulman, X.Z. Yan, N.L. Yang, C. Estournes, H. White, Rafailovich M. Langmuir 17, 5093 (2001)

    Article  CAS  Google Scholar 

  33. A. Khazaei, F. Abbasi, A.R. Moosavi-Zare, J. Sulfur Chem. 36, 364 (2015)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

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

Author information

Authors and Affiliations

  1. Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran

    Ardeshir Khazaei & Mahsa Tavasoli

  2. Department of Chemistry, Sayyed Jamaleddin Asadabadi University, Asadabad, 6541861841, Iran

    Ahmad Reza Moosavi-Zare

Authors
  1. Ardeshir Khazaei
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mahsa Tavasoli
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ahmad Reza Moosavi-Zare
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ardeshir Khazaei.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 2411 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khazaei, A., Tavasoli, M. & Moosavi-Zare, A.R. 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. Res Chem Intermed 44, 5893–5910 (2018). https://doi.org/10.1007/s11164-018-3462-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-018-3462-5

Keywords

Search

Navigation