Skip to main content
SpringerLink
Log in

La complex supported on magnetic nanoparticles: green, efficient, novel and reusable nanocatalyst for the synthesis of 5-substituted tetrazoles and the oxidation reactions in neat condition

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

Abstract

In the present work, we were interested in the synthesis of green and novel magnetic nanocatalyst by anchoring La complex on Fe3O4. The nanocatalyst was successfully synthesized and characterized by FT-IR, SEM, TGA, XRD, EDX, and ICP techniques. The designed procedure shows many benefits such as short reaction time, high yield, excellent purity, eco-friendly catalyst, easy workup and easy recovery from the reaction mixture by external magnet.

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
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. A. Jabbari, M. Nikoorazm, A. Ghorbani-Choghamarani, A. Jabbari, A facile preparation of palladium Schiff base complex supported into MCM-41 mesoporous and its catalytic application in Suzuki and Heck reactions. J. Porous. Mater. 23, 967–975 (2016). https://doi.org/10.1007/s10934-016-0154-7

    Article  CAS  Google Scholar 

  2. S.M. Baghbanian, S. Khaksar, S.M. Vahdat, M. Farhang, M. Tajbakhsh, One-step, synthesis of Hantzsch esters and polyhydroquinoline derivatives using new organocatalyst. Chin. Chem. Lett. 21, 563–567 (2010). https://doi.org/10.1016/j.cclet.2009.12.011

    Article  CAS  Google Scholar 

  3. T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, Synthesis of polyhydroquinoline, 2, 3-dihydroquinazolin-4 (1H)-one, sulfide and sulfoxide derivatives catalyzed by new copper complex supported on MCM-41. Catal Lett. 148, 857–872 (2018). https://doi.org/10.1007/s10562-018-2311-x

    Article  CAS  Google Scholar 

  4. J. Davarpanah, A.R. Kiasa, Synthesis and characterization of SBA-polyperoxyaCID: AN efficient heterogeneous solid peroxyacid catalyst for epoxidation of alkenes. Catal Commun. 46, 75–80 (2014). https://doi.org/10.1016/j.catcom.2013.11.022

    Article  CAS  Google Scholar 

  5. M.A. Zolfigol, M. Yarie, Fe3O4@TiO2@O2PO2(CH2)NHSO3H as a novel nanomagnetic catalyst: application to the preparation of 2-amino-4,6-diphenylnicotinonitriles via anomeric-based oxidation. Appl. Organometal. Chem. 31, e3598 (2017). https://doi.org/10.1002/aoc.3598

    Article  CAS  Google Scholar 

  6. A. Heidari, H. Younesi, Z. Mehraban, Removal of Ni(II), Cd(II), and Pb(II) from a ternary aqueous solution by amino functionalized mesoporous and nanomesoporous silica. J. Chem. Eng. 153, 70–79 (2009). https://doi.org/10.1016/j.cej.2009.06.016

    Article  CAS  Google Scholar 

  7. A. Benhamou, M. Baudu, Z. Derriche, J.P. Basly, Aqueous heavy metals removal on amine-functionalized Si-MCM-41 and Si-MCM-48. J. Hazard. Mater. 171, 1001–1008 (2009). https://doi.org/10.1016/j.jhazmat.2009.06.106

    Article  CAS  PubMed  Google Scholar 

  8. D. Saberi, M. Sheykhan, K. Niknam, A. Heydari, Preparation of carbon nanotube-supported α-Fe2O3@CuO nanocomposite: a highly efficient and magnetically separable catalyst in cross-coupling of aryl halides with phenols. Catal. Sci. Technol 3, 2025–2031 (2013). https://doi.org/10.1039/C3CY00082F

    Article  CAS  Google Scholar 

  9. T. Tamoradi, A. Ghorbani-Choghamarani, M. Ghadermazi, Fe3O4–adenine–Zn: a novel, green, and magnetically recoverable catalyst for the synthesis of 5-substituted tetrazoles and oxidation of sulfur containing compounds. New J. Chem 41, 11714–11721 (2017). https://doi.org/10.1039/C7NJ02337E

    Article  CAS  Google Scholar 

  10. M.A. Zolfigol, M. Kiafar, M. Yarie, A. Taherpour, M. Saeidi-Rad, Experimental and theoretical studies of the nanostructured {Fe3O4@SiO2@(CH2)3Im}C(CN)3 catalyst for 2-amino-3-cyanopyridine preparation via an anomeric based oxidation. RSC Adv. 6, 50100–50111 (2016). https://doi.org/10.1039/C6RA12299J

    Article  CAS  Google Scholar 

  11. J. Davarpanah, A.R. Kiasat, Catalytic application of silver nanoparticles immobilized to rice husk-SiO2-aminopropylsilane composite as recyclable catalyst in the aqueous reduction of nitroarenes. Catal. Commun. 41, 6–11 (2013). https://doi.org/10.1016/j.catcom.2013.06.020

    Article  CAS  Google Scholar 

  12. M.A. Zolfigol, V. Khakyzadeh, V.A.R. Moosavi-Zare, A. Rostami, A. Zare, N. Iranpoor, M.H. Beyzavi, R. Luque, A highly stable and active magnetically separable Pd nanocatalyst in aqueous phase heterogeneously catalyzed couplings. Green Chem. 15, 2132–2140 (2013). https://doi.org/10.1039/C3GC40421H

    Article  CAS  Google Scholar 

  13. A. Maleki, P. Ravaghi, M. Aghaei, H. Movahed, A novel magnetically recyclable silver-loaded cellulose-based bionanocomposite catalyst for green synthesis of tetrazolo[1,5-a]pyrimidines. Res. Chem. Intermed. 43, 5485–5494 (2017). https://doi.org/10.1007/s11164-017-2941-4

    Article  CAS  Google Scholar 

  14. A. Maleki, An efficient magnetic heterogeneous nanocatalyst for the synthesis of pyrazinophorpyrazine macrocycles. Polycycl. Aromat. Compd. 38, 402–409 (2018). https://doi.org/10.1080/10406638.2016.1221836

    Article  CAS  Google Scholar 

  15. A. Maleki, J. Rahimi, O.M. Demchuk, A.Z. Wilczewska, R. Jasiński, Green in water sonochemical synthesis of tetrazolopyrimidine derivatives by a novel core-shell magnetic nanostructure catalyst. Ultrason. Sonochem. 43, 262–271 (2018). https://doi.org/10.1016/j.ultsonch.2017.12.047

    Article  CAS  PubMed  Google Scholar 

  16. A. Shaabani, A. Maleki, A.H. Rezayan, A. Sarvary, Recent progress of isocyanide-based multicomponent reactions in Iran. Mol. Divers. 15, 41–68 (2011). https://doi.org/10.1007/s11030-010-9258-1

    Article  CAS  PubMed  Google Scholar 

  17. A. Shaabani, A. Maleki, Green and efficient synthesis of quinoxaline derivatives via ceric ammonium nitrate promoted and in situ aerobic oxidation of a a -hydroxy ketones and a α-keto oximes in aqueous media. Chem. Pharm. Bull. 56, 79–81 (2008). https://doi.org/10.1248/cpb.56.79

    Article  CAS  PubMed  Google Scholar 

  18. A. Maleki, Green oxidation protocol: selective conversions of alcohols and alkenes to aldehydes, ketones and epoxides by using a new multiwall carbon nanotube-based hybrid nanocatalyst via ultrasound irradiation. Ultrason. Sonochemistry. 40, 460–264 (2018). https://doi.org/10.1016/j.ultsonch.2017.07.020

    Article  CAS  Google Scholar 

  19. A. Maleki,·T. N. Kari, Leaking-Free, Green, double core/shell, palladium-loaded magnetic heterogeneous nanocatalyst for selective aerobic oxidation. Catal. Lett. 148, 2929–2934 (2018). https://doi.org/10.1007/s10562-018-2492-3

    Article  CAS  Google Scholar 

  20. A. Maleki, R. Rahimi, S. Maleki, Efficient oxidation and epoxidation using a chromium(VI)based magnetic nanocomposite. Environ. Chem. Lett. 14, 195–199 (2016). https://doi.org/10.1007/s10311-016-0558-2

    Article  CAS  Google Scholar 

  21. A. Maleki, M. Aghaei, R. Paydar, Highly efficient protocol for the aromatic compounds nitration catalyzed by magnetically recyclable core/shell nanocomposite. J. Iran. Chem. Soc. 14, 485–490 (2017). https://doi.org/10.1007/s13738-016-0996-6

    Article  CAS  Google Scholar 

  22. T. Tamoradi, B. Mehraban-Esfandiari, M. Ghadermazi, A. Ghorbani–Choghamarani, Immobilization of a nickel complex onto functionalized Fe3O4 nanoparticles: a green and recyclable catalyst for synthesis of 5-substituted 1H-tetrazoles and oxidation reactions. Res. Chem. Intermed. 44, 1363–1380 (2018). https://doi.org/10.1007/s11164-017-3172-4

    Article  CAS  Google Scholar 

  23. A. Ghorbani-Choghamarani, Z. Darvishnejad, B. Tahmasbi, Schiff base complexes of Ni, Co, Cr, Cd and Zn supported on magnetic nanoparticles: as efficient and recyclable catalysts for the oxidation of sulfides and oxidative coupling of thiols. Inorg. Chim. Acta 435, 223–231 (2015). https://doi.org/10.1016/j.ica.2015.07.004

    Article  CAS  Google Scholar 

  24. A. Ghorbani-Choghamarani, L. Shiri, G. Azadi, The first report on the eco-friendly synthesis of 5-substituted 1H-tetrazoles in PEG catalyzed by Cu(II) immobilized on Fe3O4@SiO2@L-arginine as a novel, recyclable and non-corrosive catalyst. RSC Adv. 6, 32653–32660 (2016). https://doi.org/10.1039/C6RA03023H

    Article  CAS  Google Scholar 

  25. A. Ghorbani-Choghamarani, B. Tahmasbi, P. Moradi, Palladium–S-propyl-2-aminobenzothioate immobilized on Fe3O4 magnetic nanoparticles as catalyst for Suzuki and Heck reactions in water or poly(ethylene glycol). Appl. Organomet. Chem. 30, 422–430 (2016). https://doi.org/10.1002/aoc.3449

    Article  CAS  Google Scholar 

  26. T. Tamoradi, A. Ghorbani-Choghamarani, M. Ghadermazi, Synthesis of a new Pd(0)-complex supported on magnetic nanoparticles and study of its catalytic activity for Suzuki and Stille reactions and synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives. Polyhedron 145, 120–130 (2018). https://doi.org/10.1016/j.poly.2018.01.016

    Article  CAS  Google Scholar 

  27. M. Hajjami, L. Shiri, A. Jahanbakhshi, Zirconium oxide complex-functionalized MCM-41 nanostructure: an efficient and reusable mesoporous catalyst for oxidation of sulfides and oxidative coupling of thiols using hydrogen peroxide. Appl. Organometal. Chem. 29, 668–673 (2015). https://doi.org/10.1002/aoc.3348

    Article  CAS  Google Scholar 

  28. A. Ghorbani-Choghamarani, P. Moradi, B. Tahmasbi, Ni–S-methylisothiourea complexes supported on boehmite nanoparticles and their application in the synthesis of 5-substituted tetrazoles. RSC Adv. 16, 56638–56646 (2016). https://doi.org/10.1039/C6RA08026J

    Article  CAS  Google Scholar 

  29. A. Ghorbani-Choghamarani, P. Zamani, Ammonium bromide as an effective and viable catalyst in the oxidation of sulfides using nitro urea and silica sulfuric acid. J. Iran. Chem. Soc. 8, 142–148 (2011). https://doi.org/10.1007/BF03246211

    Article  CAS  Google Scholar 

  30. M. Bagherzadeh, M. Zare, Chapter one—developments in tetrazole chemistry. Adv. Heterocyclic Chem. 123, 1–62 (2017). https://doi.org/10.1016/bs.aihch.2016.12.003

    Article  Google Scholar 

  31. N. Moeini, T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, Ni–S-methylisothiourea complexes supported on boehmite nanoparticles and their application in the synthesis of 5-substituted tetrazoles. RSC Adv. 6, 56638–56646 (2016). https://doi.org/10.1039/C6RA08026J

    Article  CAS  Google Scholar 

  32. M. Esmaeilpour, J. Javidi, F. Nowroozi Dodeji, M. Mokhtari, Abarghoui, Facile synthesis of 1- and 5-substituted 1H-tetrazoles catalyzed by recyclable ligand complex of copper(II) supported on superparamagnetic Fe3O4@SiO2 nanoparticles. J. Mol. Catal. A 393, 18–29 (2014). https://doi.org/10.1016/j.molcata.2014.06.001

    Article  CAS  Google Scholar 

  33. F. Abrishami, M. Ebrahimikia, F. Rafiee, Synthesis of 5-substituted 1H-tetrazoles using a recyclable heterogeneous nanonickel ferrite catalyst. Appl. Organomet. Chem. 29, 730–735 (2015). https://doi.org/10.1002/aoc.3358

    Article  CAS  Google Scholar 

  34. T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, A. Ghorbani-Choghamarani, Ni(II)-Adenine complex coated Fe3O4 nanoparticles as high reusable nanocatalyst for the synthesis of polyhydroquinoline derivatives and oxidation reactions. Appl. Organomet. Chem. 32, e3974 (2018). https://doi.org/10.1002/aoc.3974

    Article  CAS  Google Scholar 

  35. M. Nikoorazm, A. Ghorbani-Choghamarani, M. Khanmoradi, Immobilization of a vanadium complex onto functionalized nanoporous MCM-41 and its application as a catalyst for the solvent-free chemoselective oxidation of sulfide to sulfoxide. Appl. Organomet. Chem. 30, 236–241 (2016). https://doi.org/10.1002/aoc.3422

    Article  CAS  Google Scholar 

  36. M. Hajjami, L. Shiri, A. Jahanbakhshi, Zirconium oxide complex-functionalized MCM-41 nanostructure: an efficient and reusable mesoporous catalyst for oxidation of sulfides and oxidative coupling of thiols using hydrogen peroxide. Appl. Organomet. Chem. 29, 668–673 (2015). https://doi.org/10.1002/aoc.3348

    Article  CAS  Google Scholar 

  37. A. Dhakshinamoorthy, K. Pitchumani, Clay-supported ceric ammonium nitrate as an effective, viable catalyst in the oxidation of olefins, chalcones and sulfides by molecular oxygen. Catal. Commun. 10, 872–878 (2009). https://doi.org/10.1016/j.catcom.2008.12.025

    Article  CAS  Google Scholar 

  38. A. Jabbari, H. Mahdavi, M. Nikoorazm, A. Ghorbani-Choghamarani, Oxovanadium(IV) salicylidene Schiff base complex anchored on mesoporous silica MCM-41 as hybrid materials: a robust catalyst for the oxidation of sulfides. J. Porous. Mater. 22, 1111–1118 (2015). https://doi.org/10.1007/s10934-015-9986-9

    Article  CAS  Google Scholar 

  39. M. Nikoorazm, A. Ghorbani-Choghamarani, H. Mahdavi, H.S.M. Esmaeili, Efficient oxidative coupling of thiols and oxidation of sulfides using UHP in the presence of Ni or Cd salen complexes immobilized on MCM-41 mesoporous as novel and recoverable nanocatalysts. Microporous Mesoporous Mater. 211, 174–181 (2015). https://doi.org/10.1016/j.micromeso.2015.03.011

    Article  CAS  Google Scholar 

  40. U.B. Patil, K.R. Kumthekar, J.M. Nagarkar, A novel method for the synthesis of 5-substituted 1H-tetrazole from oxime and sodium azide. Tetrahedron Lett. 53, 3706–3709 (2012). https://doi.org/10.1016/j.tetlet.2012.04.093

    Article  CAS  Google Scholar 

  41. L. Lang, H. Zhou, M. Xue, X. Wang, Z. Xu, Mesoporous ZnS hollow spheres-catalyzed synthesis of 5-substituted 1H-tetrazoles. Mater. Lett. 106, 443–446 (2013). https://doi.org/10.1016/j.matlet.2013.05.067

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge the support of this work by University of Kurdistan.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, Iran

    Taiebeh Tamoradi, Asrin Irandoust & Mohammad Ghadermazi

Authors
  1. Taiebeh Tamoradi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Asrin Irandoust
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mohammad Ghadermazi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Taiebeh Tamoradi or Mohammad Ghadermazi.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tamoradi, T., Irandoust, A. & Ghadermazi, M. La complex supported on magnetic nanoparticles: green, efficient, novel and reusable nanocatalyst for the synthesis of 5-substituted tetrazoles and the oxidation reactions in neat condition. J IRAN CHEM SOC 16, 1723–1733 (2019). https://doi.org/10.1007/s13738-019-01646-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-019-01646-x

Keywords

Search

Navigation