Skip to main content
Log in

The phenyltetrazolethiol-based nickel complex: a versatile catalyst for the synthesis of diverse amidoalkyl naphthols and chromenes

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

Abstract

A novel nano-magnetic-supported phenyltetrazolethiol-based Ni complex (Fe3O4@SiO2@ CPTMS@PhenTetThiol@Ni) was synthesized, characterized with different techniques and used as a heterogeneous nano-catalyst in the following two sets of compounds: (a) synthesis of amidoalkyl naphthols from the reaction of aromatic aldehyde, 2-naphthol and acetamide/benzamide in solvent-free condition at 75 °C for an appropriate time and (b) synthesis of chromenes from the reaction of aldehyde, dimedone and malononitrile under solvent-free condition at 75 °C for an appropriate time.

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

Access this article

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

Instant access to the full article PDF.

Scheme 1
Scheme 2
Scheme 3
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Scheme 4
Scheme 5
Fig. 12
Fig. 13

Similar content being viewed by others

References

  1. L.M. Rossi, N.J.S. Costa, F.P. Silva, R. Wojcieszak, Green Chem. 16, 2906 (2014)

    Article  CAS  Google Scholar 

  2. D. Wang, D. Astruc, Chem. Rev. 114, 6949 (2014)

    Article  CAS  Google Scholar 

  3. S. Payra, A. Saha, S. Banerjee, J. Nanosci. Nanotechnol. 17, 4432 (2017)

    Article  CAS  Google Scholar 

  4. M. Mokhtary, J. Iran. Chem. Soc. 13, 1827 (2016)

    Article  CAS  Google Scholar 

  5. T. Cheng, D. Zhang, H. Li, G. Liu, Green Chem. 16, 3401 (2014)

    Article  CAS  Google Scholar 

  6. M. Duan, J.G. Shapter, Sh. Yang, Nanotechnology 29, 452001 (2018)

    Article  Google Scholar 

  7. M.A. Zolfigol, R. Ayazi, S. Baghery, RSC Adv. 5, 71942 (2015)

    Article  CAS  Google Scholar 

  8. M.A. Zolfigol, R.A. Nasrabadi, S. Baghery, V. Khakyzadeh, S. Azizian, J. Mol. Catal. A Chem. 53, 54 (2016)

    Article  Google Scholar 

  9. B. Bhushan, B. Bhagyesh, C. Suvarna, P. Kanchan, B. Pinky, S. Vikrant, P. Shailesh, S.S. Khadabadi, Rasayan, J. Chem. 2, 86 (2009)

    Google Scholar 

  10. A.R. Kiasat, A. Mouradzadegun, S.J. Saghanezhad, Chin. J. Catal. 34, 1861 (2013)

    Article  CAS  Google Scholar 

  11. G.C. Nandi, S. Samai, R. Kumar, M.S. Singh, Tetrahedron Lett. 50, 7220 (2009)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  13. J. Safaei Ghomi, S. Zahedi, M.A. Ghasemzadeh, Monatsh. Chem. 145, 1191 (2014)

    Article  CAS  Google Scholar 

  14. J.L. Peglion, J. Vian, B. Goument, N. Despaux, V. Audinot, M.J. Millan, Bioorg. Med. Chem. Lett. 7, 881 (1997)

    Article  CAS  Google Scholar 

  15. T. Dingermann, D. Steinhilber, G. Folkers, In Molecular Biology in Medicinal Chemistry, Wiley-VCH (2004).

  16. H. Matsuoka, N. Ohi, M. Mihara, H. Suzuki, K. Miyamoto, N. Maruyama, K. Tsuji, N. Kato, T. Akimoto, Y. Takeda, K. Yano, T. Kuroki, J. Med. Chem. 40, 105 (1997)

    Article  CAS  Google Scholar 

  17. J. Safaei Ghomi, S. Zahedi, Monatsh. Chem. 144, 687 (2013)

    Article  Google Scholar 

  18. A.A. Mohammadi, M.R. Asghariganjeh, A. Hadadzahmatkesh, Arab. J. Chem. 10, S2213 (2017)

    Article  CAS  Google Scholar 

  19. A. Patra, T. Mahapatra, J. Chem. Res. 34, 689 (2010)

    Article  CAS  Google Scholar 

  20. H.R. Shaterian, A. Hosseinian, M. Ghashang, Synth. Commun. 38, 3375 (2008)

    Article  CAS  Google Scholar 

  21. H.R. Shaterian, H. Yarahmadi, M. Ghashang, M. Safari Mehmandosti, Chin. J. Chem. 26, 2093 (2008)

    Article  CAS  Google Scholar 

  22. H.R. Shaterian, H. Yarahmadi, Article. Arkivoc ii 2008, 105 (2008)

    Article  Google Scholar 

  23. H. Khabazzadeh, K. Saidi, N. Seyedi, J. Chem. Sci. 121, 429 (2009)

    Article  CAS  Google Scholar 

  24. H.R. Shaterian, H. Yarahmadi, M. Ghashang, Turk. J. Chem. 33, 1 (2009)

    Google Scholar 

  25. M. Dashteh, S. Baghery, M.A. Zolfigol, Y. Bayat, A. Asgari, ChemistrySelect 4, 337 (2019)

    Article  CAS  Google Scholar 

  26. E. Altay, E.D. Nykypanchuk, J. Rzayev, ACS Nano 11, 8207 (2017)

    Article  CAS  Google Scholar 

  27. M.S. Sitze, M.S. Schreiter, E.V. Patterson, R.G. Freeman, Inorg. Chem. 40, 2298 (2001)

    Article  CAS  Google Scholar 

  28. B. Jiang, Z. Sun, L. Zhang, Y. Sun, H. Zhang, J. Appl. Polym. Sci. 135, 46280 (2018)

    Article  Google Scholar 

  29. T. Jin, Z. Xiong, X. Zhu, N. Mehio, Y. Chen, J. Hu, W. Zhang, H. Zou, H. Liu, S. Dai, A.C.S. Macro, Lett. 4, 570 (2015)

    CAS  Google Scholar 

  30. J. Afsar, M.A. Zolfigol, A. Khazaei, ChemistrySelect 3, 11134 (2018)

    Article  Google Scholar 

  31. D. Katheriya, N. Patel, H. Dadhania, A. Dadhania, J. Iran. Chem. Soc. 18, 805 (2021)

    Article  CAS  Google Scholar 

  32. M. Rohaniyan, A. Davoodnia, A. Khojastehnezhad, S.A. Beyramabadi, Eurasian. Chem. Commun. 3, 329 (2020)

    Google Scholar 

  33. F. Ghorbani, H. Kiyani, S.A. Pourmousavi, D. Ajloo, Res. Chem. Intermed. 46, 3145 (2020)

    Article  CAS  Google Scholar 

  34. R.S. Keri, M. Patil, S. Budagumpi, B.S. Sasidhar (2021). Article title. Appl. Organomet. Chem. e6316 .

  35. S.S. Dipake, S.P. Gadekar, P.B. Thombre, M.K. Lande, A.S. Rajbhoj, S.T. Gaikwad, Catal. Lett. 4, 1 (2021)

    Google Scholar 

  36. M. Torabi, M. Yarie, M.A. Zolfigol, S. Azizian, Res. Chem. Intermed. 46, 891 (2020)

    Article  CAS  Google Scholar 

  37. D.P. Narayanan, S.K. Cherikallinmel, S. Sankaran, B.N. Narayanan, J. Colloid Interf. Sci. 520, 70 (2018)

    Article  CAS  Google Scholar 

  38. S. Sayyahi, A. Azin, S.J. Saghanezhad, J. Mol. Liq. 198, 30 (2014)

    Article  CAS  Google Scholar 

  39. F. Ghorbani, S.A. Pourmousavi, H. Kiyani, Lett. Org. Chem. 18, 66 (2021)

    Article  CAS  Google Scholar 

  40. F. Li, J. Zhang, L. Wang, W. Liu, Q.A. Yousif, Polish J Chem. Technol. 22, 9 (2020)

    Article  CAS  Google Scholar 

  41. R.K. Singh, A. Dhiman, Sh. Chaudhary, D.N. Prasad, S. Kumar, Curr. Org. Chem. 24, 487 (2020)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank the Bu-Ali Sina University, Iran, Hamedan, for the financial support of this work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Davood Habibi.

Ethics declarations

Conflicts of interest

There are no conflicts of interest to be declared.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 10489 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mansouri, M., Habibi, D. & Heydari, S. The phenyltetrazolethiol-based nickel complex: a versatile catalyst for the synthesis of diverse amidoalkyl naphthols and chromenes. Res Chem Intermed 48, 683–702 (2022). https://doi.org/10.1007/s11164-021-04617-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-021-04617-1

Keywords

Navigation