Journal of the Iranian Chemical Society

, Volume 16, Issue 2, pp 365–372 | Cite as

The green synthesis of 2-amino-3-cyanopyridines using SrFe12O19 magnetic nanoparticles as efficient catalyst and their application in complexation with Hg2+ ions

  • Zohreh kheilkordi
  • Ghodsi Mohammadi ZiaraniEmail author
  • Shahriyar Bahar
  • Alireza Badiei
Original Paper


In this paper, a family of 2-amino-4,6-diphenylnicotinonitriles are prepared from aromatic aldehydes, acetophenone derivatives, malononitrile, and ammonium acetate via one-pot reaction catalyzed by SrFe12O19 magnetic nanoparticles. SrFe12O19 was an efficient, green, and reusable nanomagnetic heterogeneous catalyst with the average particles’ size of 70 nm which can be recycled and readily and separated from the reaction mixture using an external magnet. Short reaction times and high yields of desired products are the main advantages of the presented procedure. Subsequently, the spectrophotometric method was used to investigation of the complexation process between 2-amino-4,6-diphenylnicotinonitrile as organo-ligand and several metal ions such as Ag+, Cd2+, Co2+, Cr3+, Cu2+, Fe3+, Hg2+, Mn2+, Ni2+, Pb2+, and Zn2+ in CH3CN solution at 25 °C. According to the obtained results, the absorption spectra of organo-ligand in the CH3CN solution only were changed by the addition of Hg2+ ions, which indicates the formation of one absorbing complex compound between organo-ligand and Hg2+ ions. The stoichiometry of the resulting complex was calculated from the computer fitting of the molar absorbance measurements in different mole ratios.

Graphical abstract


SrFe12O19 One-pot Magnetic nanoparticles 2-amino-4,6-diphenylnicotinonitriles Solvent-free reaction Complexation 



The authors thank the Research Council of Alzahra University and the University of Tehran for the financial support.

Supplementary material

13738_2018_1514_MOESM1_ESM.docx (578 kb)
Supplementary material 1 (DOCX 578 KB)


  1. 1.
    T. Murata, M. Shimada, S. Sakakibara, T. Yoshino, H. Kadono, T. Masuda, M. Shimazaki, T. Shintani, K. Fuchikami, K. Sakai, H. Inbe, K. Takeshita, T. Niki, M. Umeda, K.B. Bacon, K.B. Ziegelbauer, T.B. Lowinger, Bioorg. Med. Chem. Lett. 13, 913 (2003)CrossRefGoogle Scholar
  2. 2.
    M. Mantri, O. de Graaf, J. Van Veldhoven, A. Göblyös, J. K. Von Frijtag Drabbe Künzel, T. Mulder-Krieger, A.P. Ijzerman, J. Med. Chem. 51, 4449 (2008)CrossRefGoogle Scholar
  3. 3.
    J. Deng, T. Sanchez, L.Q. Al-Mawsawi, R. Dayam, R.A. Yunes, A. Garofalo, M.B. Bolger, N. Neamati, Bioorg. Med. Chem. 15, 4985 (2007)CrossRefGoogle Scholar
  4. 4.
    D.H. Vyas, S.D. Tala, J.D. Akbari, M.F. Dhaduk, K.A. Joshi, H.S. Joshi, Ind. J. Chem. Sect. B. 48, 833 (2009)Google Scholar
  5. 5.
    F. Zhang, Y. Zhao, L. Sun, L. Ding, Y. Gu, P. Gong, Eur. J. Med. Chem. 46, 3149 (2011)CrossRefGoogle Scholar
  6. 6.
    N. Kumar, A. Chauhan, S. Drabu, Biomed. Pharmacother. 65, 375 (2011)CrossRefGoogle Scholar
  7. 7.
    J.J. Went, G.W. Ratheneau, E.W. Gorter, G.W. VanDosterhout, Philips Tech. Rev. 13, 194 (1951)Google Scholar
  8. 8.
    M. Mozaffari, J. Amighian, Physica B: Condensed Matter. 321, 45 (2002)CrossRefGoogle Scholar
  9. 9.
    M.V. Cabanas, J.M. Gonzalez-Calbet, M. Vallet-Regi, J. Solid. State. Chem. 115, 347 (1995)CrossRefGoogle Scholar
  10. 10.
    X. Zuo, P. Shi, S. Oliver, C. Vittoria, J. Appl. Phy. 91, 7622 (2002)CrossRefGoogle Scholar
  11. 11.
    K. Haneda, C. Miyakawa, K. Goto, Trans. Magn. 23, 3134 (1987)CrossRefGoogle Scholar
  12. 12.
    A. Ataie, I. Harris, C. Ponton, J. Mater. Sci. 30, 1429 (1995)CrossRefGoogle Scholar
  13. 13.
    C. Sürig, K.A. Hempel, D. Bonnenberg, Applied. Phys. Lett. 63, 2836 (1993)CrossRefGoogle Scholar
  14. 14.
    Z.-B. Guo, W.-P. Ding, W. Zhong, J.-R. Zhang, Y.-W. Du, J. Magn. Magn. Mater. 175, 333 (1997)CrossRefGoogle Scholar
  15. 15.
    S.V. Ketov, Y.D. Yagodkin, A.L. Lebed, Y.V. Chernopyatova, K. Khlopkov, J. Magn. Magn. Mater. 300, 479 (2006)CrossRefGoogle Scholar
  16. 16.
    L. Qiao, L. You, J. Zheng, L. Jiang, J. Sheng, J. Magn. Magn. Mater. 318, 74 (2007)CrossRefGoogle Scholar
  17. 17.
    V. Pankov, M. Pernet, P. Germi, P. Mollard, J. Magn. Magn. Mater. 120, 69 (1993)CrossRefGoogle Scholar
  18. 18.
    Z. Zi, Y. Sun, X. Zhu, Z. Yang, W. Song, J. Magn. Magn. Mater. 320, 2746 (2008)CrossRefGoogle Scholar
  19. 19.
    H.C. Visser, D.N. Reinhoudt, F. de Jong, Chem. Soc. Rev. 23, 75 (1994)CrossRefGoogle Scholar
  20. 20.
    R.M. Izatt, K. Pawlak, J.S. Bradshaw, R.L. Bruening, Chem. Rev. 95, 2529 (1995)CrossRefGoogle Scholar
  21. 21.
    R.D. Hancock, A.E. Martell, Chem. Rev. 89, 1875 (1989)CrossRefGoogle Scholar
  22. 22.
    A. Nezhadali, Z. Es’haghi, S. Bahar, A. Banaei, J.A. Shiran, J. Braz. Chem. Soc. 27, 99 (2016)Google Scholar
  23. 23.
    S. Alamolhoda, S.S. Ebrahimi, A. Badiei, Iran. Int. J. Sci. 5, 173 (2004)Google Scholar
  24. 24.
    S. Alamolhoda, S.S. Ebrahimi, A. Badiei, J. Magn. Magn. Mater. 303, 69 (2006)CrossRefGoogle Scholar
  25. 25.
    M.G. Hasab, S.S. Ebrahimi, A. Badiei, J. Eur. Ceram. Soc. 27, 3637 (2007)CrossRefGoogle Scholar
  26. 26.
    R. Gupta, A. Jain, M. Jain, R. Joshi, Technol. Bull. Korean Chem. Soc. 31, 3180 (2010)CrossRefGoogle Scholar
  27. 27.
    M.A. Zolfigol, M. Kiafar, M. Yarie, RSC Adv. 6, 50100 (2016)CrossRefGoogle Scholar
  28. 28.
    R. Khalifeh, M. Ghamari, J. Braz. Chem. Soc. 27, 759 (2016)Google Scholar
  29. 29.
    S.S. Mansoor, K. Aswin, K. Logaiya, P.N. Sudhan, S. Malik, Res. Chem. Intermed. 40, 871 (2014)CrossRefGoogle Scholar
  30. 30.
    D. Khalili, Tetrahedron Lett. 57, 1721 (2016)CrossRefGoogle Scholar
  31. 31.
    S. Behrouz, Acc. Chem. Res. 40, 540 (2016)Google Scholar
  32. 32.
    M.A. Zolfigol, M. Yarie, Appl. Organometal. Chem. 31, 1 (2017)Google Scholar
  33. 33.
    M. Abdollahi-Alibeik, N. Sadeghi- Vasafi, A. Moaddeli, A. Rezaeipoor-Anari, Res. Chem. Intermed. 42, 2867 (2015)CrossRefGoogle Scholar
  34. 34.
    M. Zadpour, F.K. Behbahani, Monatsh. Chem. 146, 1865 (2015)CrossRefGoogle Scholar
  35. 35.
    C. Kurumurthy, R. Naresh Kumar, T. Yakaiah, P. Shanthan Rao, B. Narsaiah, Res. Chem. Intermed. 41, 3193 (2015)CrossRefGoogle Scholar
  36. 36.
    J. Tang, L. Wang, Y. Yao, L. Zhang, W. Wang, Tetrahedron Lett. 52, 509 (2011)CrossRefGoogle Scholar
  37. 37.
    G. Mohammadi Ziarani, Z. Kazemi Asl, P. Gholamzadeh, A. Badiei, M. Afshar, J. Sol–Gel. Sci. Technol. 85, 103 (2018)CrossRefGoogle Scholar
  38. 38.
    G. Mohammadi Ziarani, Z. Kazemi Asl, P. Gholamzadeh, A. Badiei, M. Afshar, Appl. Organometal. Chem. 31, e3830 (2017)CrossRefGoogle Scholar
  39. 39.
    H. Shafiekhani, F. Nezam, S. Bahar, J. Serb. Chem. Soc. 82, 317 (2017)Google Scholar

Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  • Zohreh kheilkordi
    • 1
  • Ghodsi Mohammadi Ziarani
    • 1
    Email author
  • Shahriyar Bahar
    • 1
  • Alireza Badiei
    • 2
  1. 1.Department of ChemistryAlzahra UniversityTehranIran
  2. 2.School of Chemistry, College of ScienceUniversity of TehranTehranIran

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