Skip to main content
SpringerLink
Log in

1, 4-Diazabicyclo[2.2.2]octane-sulfonic acid immobilized on magnetic Fe3O4@SiO2 nanoparticles: a novel and recyclable catalyst for the one-pot synthesis of 4-aryl-NH-1, 2, 3-triazoles

  • Regular Article
  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

This article is dedicated to the memory of Mozafar Rabiei.

Abstract

In this study, the surface of silica-coated magnetic nanoparticles (Fe3O4@SiO2) were successfully functionalized by an organic ligand of 1, 4-Diazabicyclo[2.2.2]octane (DABCO)-sulfonic acid and used as a highly efficient catalyst for the synthesis of 4-aryl-NH-1, 2, 3-triazoles from the benzyl alcohol derivatives, nitromethane and sodium azide in ethanol. Furthermore, this catalyst could be recovered and reused five times without noticeable loss of activity.

Graphic Abstract

Fe3O4@SiO2@TCT-DABCO-SO3H nanoparticles were successfully synthesized and used as a novel, recyclable, efficient and heterogeneous catalyst for the synthesis of 4-aryl-NH-1, 2, 3-triazoles.

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
Figure 1
Figure 2
Figure 3
Figure 4
Figure 5
Figure 6
Figure 7
Scheme 2
Scheme 3
Figure 8

Similar content being viewed by others

Reference

  1. (a) Chabre Y M and Roy R 2008 Recent trends in glycodendrimer syntheses and applications Curr. Top. Med. Chem. 8 1237; (b) Colombo M and Peretto I 2008 Chemistry strategies in early drug discovery: an overview of recent trends Drug. Discov. Today 13 677; (c) Hanselmann R, Job G E, Johnson G and Lou R L J G 2010 Synthesis of an antibacterial compound containing a 1, 4-substituted 1 H-1, 2, 3-triazole: A scalable alternative to the “click” reaction Org. Process Res. Dev. 14 152; (d) Moumne R, Larue V, Seijo B, Lecourt T, Micouin L and Tisne C 2010 Org. Biomol. Chem. 8 1154

  2. He X P, Xie J, Tang Y, Li J and Chen G R 2012 CuAAC click chemistry accelerates the discovery of novel chemical scaffolds as promising protein tyrosine phosphatases inhibitors Curr. Med. Chem. 19 2399

    CAS  Google Scholar 

  3. Hu L, Mück-Lichtenfeld C, Wang T, He G, Gao M and Zhao J 2016 Reaction between Azidyl Radicals and Alkynes: A Straightforward Approach to NH-1, 2, 3-Triazoles Chem. Eur. J. 22 911

    Article  CAS  Google Scholar 

  4. (a) Jin T, Kamijo S and Yamamoto Y 2004 Copper-Catalyzed Synthesis of N-Unsubstituted 1, 2, 3-Triazoles from Nonactivated Terminal Alkynes Eur. J. Org. Chem. 18 3789; (b) Kalisiak J, Sharpless K B and Fokin V V 2008 Efficient synthesis of 2-substituted-1, 2, 3-triazoles Org. Lett. 10 3171; (c) Cohrt A E, Jensen J F and Nielsen T E 2010 Traceless Azido Linker for the Solid-Phase Synthesis of N H-1, 2, 3-Triazoles via Cu-Catalyzed Azide–Alkyne Cycloaddition Reactions Org. Lett. 12 5414

  5. Barluenga J, Valdés C, Beltrán G, Escribano M and Aznar F 2006 Developments in Pd Catalysis: Synthesis of 1H-1, 2, 3-Triazoles from Sodium Azide and Alkenyl Bromides Angew. Chem. Int. Edit. 45 6893

    Article  CAS  Google Scholar 

  6. Quan X J, Ren Z H, Wang Y Y and Guan Z H 2014 p-Toluenesulfonic acid mediated 1, 3-dipolar cycloaddition of nitroolefins with NaN3 for synthesis of 4-aryl-NH-1, 2, 3-triazoles Org. Lett. 16 5728

    CAS  Google Scholar 

  7. Zhang W, Kuang C and Yang Q 2010 Palladium-catalyzed one-pot synthesis of 4-aryl-1H-1, 2, 3-triazoles from anti-3-aryl-2, 3-dibromopropanoic acids and sodium azide Synthesis 2010 283

  8. (a) Bhuyan P, Bhorali P, Islam I, Bhuyan A J and Saikia L 2018 Magnetically recoverable copper ferrite catalyzed cascade synthesis of 4-Aryl-1H-1, 2, 3-triazoles under microwave irradiation Tetrahedron Lett. 59 1587; (b) Mirzaei-Mosbat M, Ghorbani-Vaghei R and Sarmast N 2019 One-pot Synthesis of 4-Aryl-NH-1,2,3-triazoles in Presence of Fe3O4@SiO2@Propyl-HMTA as a New Basic Catalyst ChemistrySelect 4 1731; (c) Wu L, Wang X, Chen Y, Huang Q, Lin Q and Wu M 2016 4-Aryl-NH-1, 2, 3-Triazoles via Multicomponent Reaction of Aldehydes, Nitroalkanes, and Sodium Azide Synlett 27 437

  9. Johnson J A, Baskin J M, Bertozzi C R, Koberstein J T and Turro N J 2008 Copper-free click chemistry for the in situ crosslinking of photodegradable star polymers Chem. Commun. 26 3064

    Article  Google Scholar 

  10. Gierlich J, Burley G A, Gramlich P M, Hammond D M and Carell T 2006 Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified DNA Org. Lett. 8 3639

    CAS  Google Scholar 

  11. Polshettiwar V, Baruwati B and Varma R S 2009 Magnetic nanoparticle-supported glutathione: A conceptually sustainable organocatalyst Chem. Commun. 14 1837

    Google Scholar 

  12. Baig RN and Varma R S 2013 Copper on chitosan: a recyclable heterogeneous catalyst for azide–alkyne cycloaddition reactions in water Green Chem. 15 1839

    Article  CAS  Google Scholar 

  13. Polshettiwar V, Baruwati B and Varma R S 2009 Nanoparticle-supported and magnetically recoverable nickel catalyst: a robust and economic hydrogenation and transfer hydrogenation protocol Green Chem. 11 127

    Article  CAS  Google Scholar 

  14. Polshettiwar V and Varma R S 2010 Nano-organocatalyst: magnetically retrievable ferrite-anchored glutathione for microwave- assisted Paal–Knorr reaction, aza-Michael addition, and pyrazole synthesis Tetrahedron 66 1091

  15. Dyson P J and Jessop P G 2016 Solvent effects in catalysis: rational improvements of catalysts via manipulation of solvent interactions Catal. Sci. Technol. 6 3302

    Article  CAS  Google Scholar 

  16. Johnson J A, Baskin J M, Bertozzi C R, Koberstein J T and Turro N J 2008 Copper-free click chemistry for the in situ crosslinking of photodegradable star polymers Chem. Commun. 26 3064

    Google Scholar 

  17. Capello C, Fischer U and Hungerbühler K 2007 what is a green solvent? A comprehensive framework for the environmental assessment of solvents Green Chem. 9 927

    CAS  Google Scholar 

  18. Yazdani E, Azizi K and Nakisa A 2015 Boric Acid-Functionalized Fe3O4@SiO2 as a Novel Superparamagnetically Recoverable Nano Catalyst for Mukaiyama-Aldol Reaction J. Org. Chem. 1 27

    Google Scholar 

  19. Jain S L and Sain B 2006 Perfluorinated resinsulphonic acid (Nafion-H1) catalyzed highly efficient oxidations of organic compounds with hydrogen peroxide Appl. Catal. A 301 259

    Article  CAS  Google Scholar 

  20. (a) Liu L, Ai Y, Li D, Qi L, Zhou J, Tang Z and Sun H B 2017 Recyclable Acid–Base Bifunctional Core–Shell–Shell Nanosphere Catalyzed Synthesis of 5-Aryl-1H-1, 2, 3-triazoles through the “One-Pot” Cyclization of Aldehydes, Nitromethane, and Sodium Azide Chem. Cat. Chem. 9 3131; (b) Paris E, Bigi F, Cauzzi D, Maggi R and Maestri G 2018 Oxidative dimerization of anilines with heterogeneous sulfonic acid catalysts Green Chem. 20 382; (c) Jain S L and Sain B 2006 Perfluorinated resinsulphonic acid (Nafion-H®) catalyzed highly efficient oxidations of organic compounds with hydrogen peroxide Appl. Catal. A 301 259

  21. Wua L, Wanga X, Chena Y, Huanga Q, Lin Q and Wua M 2016 4-Aryl-NH-1,2,3-Triazoles via Multicomponent Reaction of Aldehydes, Nitroalkanes, and Sodium Azide Synlett 27 437

    Google Scholar 

  22. Liu L, Ai Y, Li D, Qi L, Zhou J, Tang Z, Shao Z, Liang Q and Sun H-B 2017 Recyclable Acid-Base Bifunctional Core-Shell-Shell Nanosphere Catalyzed Synthesis of 5-Aryl-NH-1,2,3-triazoles via “One-Pot” Cyclization of Aldehyde, Nitromethane and NaN3 Chem. Cat. Chem. 3131

  23. Hu Q, Liu Y, Deng X, Li Y and Chen Y 2016 Aluminium(III) Chloride-Catalyzed Three-Component Condensation of Aromatic Aldehydes, Nitroalkanes and Sodium Azide for the Synthesis of 4-Aryl-NH-1,2,3-triazoles Adv. Synth. Catal. 358 1689

    Article  CAS  Google Scholar 

  24. Bhuyan P, Bhorali P, Islam I, Bhuyan A J and Saikia L 2018 Magnetically recoverable copperferrite catalyzed cascade synthesis of 4-Aryl-NH-1,2,3-triazolesunder microwave irradiation Tetrahedron Lett. 59 1587

  25. Li D, Liu L, Tian Y, Ai Y, Tang Z, Sun H-B and Zhang G 2017 a flow strategy for the rapid, safe and scalable synthesis of N-H 1,2,3-triazoles via acetic acid mediated cycloaddition between nitroalkene and NaN3 Tetrahedron 73 3959

Download references

Acknowledgements

We gratefully acknowledge the financial support from the Research Council of Tarbiat Modares University.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Tarbiat Modares University, Tehran, 14117-13116, Iran

    MASOUMEH JADIDI NEJAD, FARZANE PAZOKI, SEPIDEH BAGHERI, ELAHE YAZDANI & AKBAR HEYDARI

Authors
  1. MASOUMEH JADIDI NEJAD
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. FARZANE PAZOKI
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. SEPIDEH BAGHERI
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. ELAHE YAZDANI
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. AKBAR HEYDARI
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to AKBAR HEYDARI.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 1657 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

JADIDI NEJAD, M., PAZOKI, F., BAGHERI, S. et al. 1, 4-Diazabicyclo[2.2.2]octane-sulfonic acid immobilized on magnetic Fe3O4@SiO2 nanoparticles: a novel and recyclable catalyst for the one-pot synthesis of 4-aryl-NH-1, 2, 3-triazoles. J Chem Sci 132, 62 (2020). https://doi.org/10.1007/s12039-020-01761-w

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s12039-020-01761-w

Keywords

Search

Navigation