Skip to main content

Advertisement

SpringerLink
Log in

Tannic Acid-Cu-modified Fe3O4@SiO2 nanoparticles (Fe3O4@SiO2@TA-Cu NPs): New recyclable magnetic catalyst for the three-component synthesis of 2-amino-3,5-dicarbonitrile-6-thio-pyridines

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

Abstract

An effectual encapsulation–functionalization procedure for preparing high-activity magnetic Fe3O4@SiO2@Tannic Acid-Cu (Fe3O4@SiO2@TA-Cu) nanocomposite was described. Tannic acid-Cu complexes were uniformly protected on the surface of Fe3O4@SiO2 nanoparticles. The newly prepared catalyst was characterized by XRD, FT-IR, SEM, and EDX. The obtained nanocomposites showed excellent catalytic performance and good stability for the one-pot synthesis of 2-amino-3,5-dicarbonitrile-6-thio-pyridines via three-component condensations of aldehydes, malononitrile, and thiophenols in water. The catalyst was separated by a magnet and reused at least five times without remarkable degradation in the performance. The desired products were prepared in high yields by an easy workup procedure with this protocol.

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
Scheme 2
Scheme 3
Fig. 5

Similar content being viewed by others

References

  1. T.L.S. Kishbaugh, Curr. Top. Med. Chem. 16, 3274 (2016)

    Article  CAS  PubMed  Google Scholar 

  2. M. Alrooqi, S. Khan, F.A. Alhumaydhi, S.A. Asiri, M. Alshamrani, M.M. Mashraqi, A. Alzamami, A.M. Alshahrani, A.A. Aldahish, Anticancer. Agents. Med. Chem. (2022). https://doi.org/10.2174/1871520622666220324102849

    Article  Google Scholar 

  3. H. Chen, W. Zhang, R. Tam, A.K. Raney, PCT Int. Appl. WO 2005058315 A1 20050630, (2005).

  4. S.B. Levy, M.N. Alekshun, B.L. Podlogar, K. Ohemeng, A.K. Verma, T. Warchol, B. Bhatia, T. Bowser, M. Grier, US Patent Appl. 2005124678 A1 20050609 (2005).

  5. B.C.H. May, J.A. Zorn, J. Witkop, J. Sherrill, A.C. Wallace, G. Legname, S.B. Prusiner, F.E. Cohen, J. Med. Chem 50, 65 (2007)

    Article  CAS  PubMed  Google Scholar 

  6. M.T. Cocco, C. Congiu, V. Lilliu, V. Onnis, Eur. J. Med. Chem 40, 1365 (2005)

    Article  CAS  PubMed  Google Scholar 

  7. H. Harada, S. Watanuki, T. Takuwa, K. Kawaguchi, T. Okazaki, Y. Hirano, C. Saitoh, PCT. Int. Appl. WO 2002006237 A1 20020124, (2002).

  8. B.B. Fredholm, A.P.I. Jzerman, K.A. Jacobson, K.N. Klotz, J. Linden, Pharmacol. Rev 53, 527 (2001)

    CAS  PubMed  Google Scholar 

  9. C. Alonso, M. Fuertes, E. Martín-Encinas, A. Selas, G. Rubiales, C. Tesauro, B.K. Knudssen, F. Palacios, Eur. J. Med. Chem 149, 225 (2018)

    Article  CAS  PubMed  Google Scholar 

  10. A.R. Moosavi-Zare, H. Goudarziafshar, Z. Jalilian, Prog. Chem. Biochem. Res 2, 59 (2019)

    Article  CAS  Google Scholar 

  11. M. Aghazadeh, Prog. Chem. Biochem. Res 2, 34 (2019)

    Article  CAS  Google Scholar 

  12. J.D. Sunderhaus, S.F. Martin, Chem. Eur. J 15, 1300–1308 (2009)

    Article  CAS  PubMed  Google Scholar 

  13. B. Ganem, Acc. Chem. Res 42, 463 (2009)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. S.K. Kundu, J. Mondal, A. Bhaumik, Dalton. Trans 5, 10515 (2013)

    Article  Google Scholar 

  15. S.K. Kundu, A. Bhaumik, RSC. Adv 5, 32730 (2015)

    Article  CAS  Google Scholar 

  16. S. Ray, P. Das, A. Bhaumik, M. Pramanik, C. Mukhopadhyay, Recycl. Catal 1, 34 (2014)

    Google Scholar 

  17. B. Borah, K. D. Dwivedi, L. Raju Chowhan, Polycycl. Aromat. Compd (2021). DOI: https://doi.org/10.1080/10406638.2021.1962923.

  18. D. Bayramoğlu, M. Güllü, Polycycl. Aromat. Compd (2021). https://doi.org/10.1080/10406638.2021.1915806

    Article  Google Scholar 

  19. S. Kamalifar, H. Kiyani, Polycycl. Aromat. Compd (2021). https://doi.org/10.1080/10406638.2021.1872656

    Article  Google Scholar 

  20. B.R. Nemallapudi, D.R. Guda, N. Ummadi, B. Avula, G.V. Zyryanov, C.S. Reddy, S. Gundala, New Methods for Synthesis of 1,2,3-Triazoles: A Review. Polycycl. Aromati. Compound. (2021). https://doi.org/10.1080/10406638.2020.1866038

    Article  Google Scholar 

  21. H. Thacker, V. Ram, P.N. Dave, Prog. Chem. Biochem. Res 2, 84 (2019)

    Article  CAS  Google Scholar 

  22. K. Kamari, A. Taheri, J. Taiwan. Inst. Chem. Eng 86, 230 (2018)

    Article  CAS  Google Scholar 

  23. Z. Ghadamyari, A. Khojastehnezhad, S.M. Seyedi, A. Shiri, ChemistrySelect 4, 10920 (2019)

    Article  CAS  Google Scholar 

  24. F. Tajfirooz, A. Davoodnia, M. Pordel, M. Ebrahimi, A. Khojastehnezhad, Appl. Organomet. Chem 32, e3930 (2018)

    Article  Google Scholar 

  25. H. Ebrahimiasl, D. Azarifar, J. Rakhtshah, H. Keypour, M. Mahmoudabadi, Appl. Organomet. Chem 34, e5769 (2020)

    CAS  Google Scholar 

  26. N.M. Evdokimov, A.S. Kireev, A.A. Yakovenko, M.Y. Antipin, I.V. Magedov, A. Kornienko, J. Org. Chem 72, 3443 (2007)

    Article  CAS  PubMed  Google Scholar 

  27. A. Allahi, B. Akhlaghinia, Phosphorus. Sulfur. Silicon. Relat. Elem 196, 328 (2021)

    Article  CAS  Google Scholar 

  28. R. Mamgain, R. Singh, D.S. Rawat, J. Heterocycl. Chem 46, 69 (2009)

    Article  CAS  Google Scholar 

  29. K. Niknam, A.R. Hosseini, J. Org. Chem. Res 3, 16 (2017)

    Google Scholar 

  30. M. Nasim Khan, S. Pal, T. Parvin, Lokman H. Choudhury, RSC. Adv 2, 12305 (2012).

  31. M. Kidwai, R. Chauhan, J. Iran. Chem. Soc 11, 1005 (2014)

    Article  CAS  Google Scholar 

  32. M.M. Heravi, M. Khorshidi, Y.S. Beheshtia, B. Baghernejad, Bull. Korean. Chem. Soc 31, 1343 (2010)

    Article  CAS  Google Scholar 

  33. V.T. Kamble, S.T. Atkore, P.M. Pisal, M. Sadaf, R.V. Thakre, Iran. Chem. Commun 4, 186 (2016)

    CAS  Google Scholar 

  34. M. Kantam, K. Mahendar, S. Bhargava, J. Chem. Sci 122, 63 (2010)

    Article  CAS  Google Scholar 

  35. M.R. Poor Heravi, F. Fakhr, Tetrahedron. Lett 52, 6779 (2011).

  36. V. Pravin, B. Bapurao, S. Murlidhar, Chin. J. Chem 29, 1049 (2011)

    Article  Google Scholar 

  37. B. Das, B. Ravikanth, A.S. Kumar, B.S. Kanth, J. Heterocycl. Chem 46, 1208 (2009)

    Article  CAS  Google Scholar 

  38. P.V. Shinde, V.B. Labade, B.B. Shingate, M.S. Shingare, J. Mol. Catal. A Chem 336, 100 (2011)

    Article  CAS  Google Scholar 

  39. J. Safaei-Ghomi, M.A. Ghasemzadeh, M. Mehrabi, Sci. Iran 20, 549 (2013)

    CAS  Google Scholar 

  40. M.S. Pandharpatte, H.A. Osman, A.M. Osman, G.M. Nazeruddin, Chem. Sci. Trans 6, 1 (2017)

    CAS  Google Scholar 

  41. S. Sobhani, M, Honarmand. C. R. Chim 16, 279 (2013)

    Article  CAS  Google Scholar 

  42. B.C. Ranu, R. Jana, S. Sowmiah, J. Org. Chem 72, 3152 (2007)

    Article  CAS  PubMed  Google Scholar 

  43. A. Davoodnia, P. Attar, H. Eshghi, A. Morsali, N. Tavakoli Hoseini, A. Tavakoli-Nishaburi, Asian. J. Chem 23, 1273 (2011).

  44. M. Sridhar, B.C. Ramanaiah, C. Narsaiah, B. Mahesh, M. Kumaraswamy, K.K.R. Mallu, V.M. Ankathi, PSh. Rao, Tetrahedron. Lett 50, 3897 (2009)

    Article  CAS  Google Scholar 

  45. S.S. Kottawar, S.A. Siddiqui, S.R. Bhusare, Heterocycl. Commun 18, 249 (2012)

    Article  CAS  Google Scholar 

  46. S. Sobhani, S.M. Honarmand, Appl. Catal. A: Gen 467, 456 (2013)

    Article  CAS  Google Scholar 

  47. S. Banerjee, G. Sereda, Tetrahedron. Lett 50, 6959 (2009)

    Article  CAS  Google Scholar 

  48. J. Safaei-Ghomi, M.A. Ghasemzadeh, J. Sulphur, Chem 34, 233 (2013)

    CAS  Google Scholar 

  49. P.V. Shinde, S.S. Sonar, B.B. Shingate, M.S. Shingare, Tetrahedron. Lett 52, 1309 (2010)

    Article  Google Scholar 

  50. M.S. Su, X.J. Ji, B.B. Zhao, M. Tian, J.J. Ma, J. Chem. Soc. Pak 37, 1130 (2015)

    CAS  Google Scholar 

  51. M. Thimmaiah, P. Li, S. Regati, B. Chen, J.C. Zhao, Tetrahedron. Lett 53, 4870 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  52. D. Li, X. Xu, X. Wang, R. Li, C. Cai, T. Sun, Y. Zhao, L. Chen, J. Xu, N. Zhao, ACS. Appl. Nano. Mater 2, 3510 (2019)

    Article  CAS  Google Scholar 

  53. W. Zhou, Y. Zhou, Y. Liang, X.H. Feng, H. Zhou, RSC. Adv 5, 50505 (2015)

    Article  CAS  Google Scholar 

  54. B.S. Kumar, A.J. Amali, K. Pitchumani, ACS. Appl. Mater. Interfaces 7, 22907 (2015)

    Google Scholar 

  55. H. Ejima, J.J. Richardson, K. Liang, J.P. Best, M.P. Koeverden, G.K. Such, J.W. Cui, F. Caruso, Science 341, 154 (2013)

    Article  CAS  PubMed  Google Scholar 

  56. J.L. Guo, Y. Ping, H. Ejima, K. Alt, M. Meissner, J.J. Richardson, Y. Yan, K. Peter, D. Elverfeldt, C.E. Hagemeyer, F. Caruso, Angew. Chem. Int. Ed 53, 5546 (2014)

    Article  CAS  Google Scholar 

  57. A.R. Kiasat, J. Davarpanah, J. Mol. Catal. A Chem 373, 46 (2013)

    Article  CAS  Google Scholar 

  58. S. Asgari, Z. Fakhari, S. Berijani, J. Nanostruct 4, 55 (2014)

    Google Scholar 

  59. Y.S. Lia, J.S. Church, A.L. Woodhead, J. Magn. Magn. Mater 324, 1543 (2012)

    Article  Google Scholar 

  60. M.A. Pantoja-Castroa, H. González-Rodríguez, Rev. Latinoam. Quím. 39, 108 (2011)

    Google Scholar 

  61. K. Rajar, R. Ali Soomro, Z.H. Ibupoto, S.A. Balouch, Int. J. Food. Prop 20, 1359 (2017).

  62. P. K. Raul, S. Senapati, A.K. Sahoo, I.M. Umlong, R.R. Devi, A.J Thakur, V. Veer, RSC. Adv 4, 40580 (2014).

  63. R. Zhang, L. Li, J. Liu, RSC. Adv 5, 40785 (2015)

    Article  CAS  Google Scholar 

  64. R. Kumar, M.A. Barakat, E.M. Soliman, J. Ind. Eng. Chem 20, 2992 (2014)

    Article  CAS  Google Scholar 

  65. H. Veisi, M. Pirhayati, A. Kakanejadifard, P. Mohammadi, M.R. Abdi, J. Gholami, S. Hemmati, ChemistrySelect 3, 1820 (2018)

    Article  CAS  Google Scholar 

  66. F. Karimi, M. Yarie, M.A. Zolfigol, Mol. Catal 497, 111201 (2020)

    Article  CAS  Google Scholar 

Download references

Funding

The authors gratefully acknowledge the Research Council of the University of Gonabad for financial support.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, University of Gonabad, Gonabad, Iran

    Azam Karimian, Mahdieh Namvar–Mahboub, Fatemeh Binabaji & Sadegh Rajabi

Authors
  1. Azam Karimian
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mahdieh Namvar–Mahboub
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Fatemeh Binabaji
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Sadegh Rajabi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Azam Karimian.

Ethics declarations

Conflict of interest

No potential conflict of interest was reported by the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Karimian, A., Namvar–Mahboub, M., Binabaji, F. et al. Tannic Acid-Cu-modified Fe3O4@SiO2 nanoparticles (Fe3O4@SiO2@TA-Cu NPs): New recyclable magnetic catalyst for the three-component synthesis of 2-amino-3,5-dicarbonitrile-6-thio-pyridines. J IRAN CHEM SOC 19, 4397–4409 (2022). https://doi.org/10.1007/s13738-022-02608-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-022-02608-6

Keywords

Search

Navigation