Journal of the Iranian Chemical Society

, Volume 15, Issue 7, pp 1633–1637 | Cite as

Synthesis of spiro[pyrazoloquinoline-oxindoles] and spiro[chromenopyrazolo-oxindoles] promoted by guanidine-functionalized magnetic Fe3O4 nanoparticles

  • Fatemeh Alemi Tameh
  • Javad Safaei-Ghomi
Original Paper


Magnetic nanoparticles (MNPs) Fe3O4-immobilized guanidine (Fe3O4 MNPs-guanidine) have been used as an efficient catalyst for the preparation of spiro[pyrazoloquinoline-oxindoles] and spiro[chromenopyrazolo-oxindoles] by four-component reactions of phenylhydrazine or hydrazine hydrate, isatins, ketoesters and naphthylamine or 2-naphthol under reflux condition in ethanol. This method provides several advantages including mild reaction conditions, the applicability to a wide range of substrates, the reusability of the catalyst and low catalyst loading.


Fe3O4 nanoparticles Heterogeneous catalyst Spirooxindoles One pot reaction 



The authors gratefully acknowledge the financial support of this work by the Research Affairs Office of the Islamic Azad University Tehran Branch, Tehran, I. R. Iran.

Supplementary material

13738_2018_1361_MOESM1_ESM.docx (965 kb)
Supplementary material 1 (DOCX 965 kb)


  1. 1.
    M. Kitajima, J. Nat. Med. 61, 14 (2007)CrossRefGoogle Scholar
  2. 2.
    R. Pandey, S.C. Singh, M.M. Gupta, Phytochem 67, 2164 (2006)CrossRefGoogle Scholar
  3. 3.
    C. Pellegrini, M. Weher, H.-J. Borschberg, Helv. Chim. Acta 79, 151 (1996)CrossRefGoogle Scholar
  4. 4.
    G. Bhaskar, Y. Arun, C. Balachandran, C. Saikumar, P.T. Perumal, Eur. J. Med. Chem. 51, 79 (2012)CrossRefPubMedGoogle Scholar
  5. 5.
    A.H. Abdel-Rahman, E.M. Keshk, M.A. Hanna, S.M. El-Bady, Bioorg. Med. Chem. 12, 2483 (2004)CrossRefPubMedGoogle Scholar
  6. 6.
    G. Wu, L. Ouyang, J. Liu, S. Zeng, W. Huang, B. Han, F. Wu, G. He, M. Xiang, Mol. Divers. 17, 271 (2013)CrossRefPubMedGoogle Scholar
  7. 7.
    G. Chen, H.P. He, J. Ding, X.J. Hao, Heterocycl. Commun. 15, 355 (2009)CrossRefGoogle Scholar
  8. 8.
    A.S. Girgis, Eur. J. Med. Chem. 44, 1257 (2009)CrossRefPubMedGoogle Scholar
  9. 9.
    R. Murugan, S. Anbazhagan, S.S. Narayanan, Eur. J. Med. Chem. 44, 3272 (2009)CrossRefPubMedGoogle Scholar
  10. 10.
    T.L. Pavlovska, R.G. Redkin, V.V. Lipson, D.V. Atamanuk, Mol. Divers. 20, 299 (2016)CrossRefPubMedGoogle Scholar
  11. 11.
    J. Safaei-Ghomi, M. Navvab, H. Shahbazi-Alavi, Ultrason. Sonochem. 31, 102 (2016)CrossRefPubMedGoogle Scholar
  12. 12.
    J. Safaei-Ghomi, H. Shahbazi-Alavi, R. Sadeghzadeh, A. Ziarati, Res. Chem. Intermed. 42, 8143 (2016)CrossRefGoogle Scholar
  13. 13.
    V. Estévez, M. Villacampa, J.C. Menendez, Chem. Soc. Rev. 39, 4402 (2010)CrossRefPubMedGoogle Scholar
  14. 14.
    J. Safaei-Ghomi, H. Shahbazi-Alavi, P. Babaei, Z. Naturforsch. 71b, 849 (2016)CrossRefGoogle Scholar
  15. 15.
    C.W. Lim, I.S. Lee, Nano Today 5, 412 (2010)CrossRefGoogle Scholar
  16. 16.
    A.H. Lu, E.L. Salaba, F. Schuth, Angew. Chem. Int. Ed. 46, 1222 (2007)CrossRefGoogle Scholar
  17. 17.
    A. Kumar, V. Kumar, Chem. Rev. 114, 7044 (2014)CrossRefPubMedGoogle Scholar
  18. 18.
    A. Rostami, B. Atashkar, D. Moradi, Appl. Catal. A Gen. 467, 7 (2013)CrossRefGoogle Scholar
  19. 19.
    S.Y. Lee, M.T. Harris, J. Colloid Interface Sci. 293, 401 (2006)CrossRefPubMedGoogle Scholar
  20. 20.
    H. Hosseinjani-Pirdehi, K. Rad-Moghadam, L. Youseftabar-Miri, Tetrahedron 70, 1780 (2014)CrossRefGoogle Scholar
  21. 21.
    R. Ghahremanzadeh, F. Fereshtehnejad, Z. Yasaei, T. Amanpour, A. Bazgir, J. Heterocycl. Chem. 47, 967 (2010)CrossRefGoogle Scholar
  22. 22.
    S. Ahadi, Z. Yasaei, A. Bazgir, J. Heterocycl. Chem. 47, 1090 (2010)CrossRefGoogle Scholar
  23. 23.
    M. Mirhosseini Moghaddam, A. Bazgir, M.M. Akhondi, R. Ghahremanzadeh, Chin. J. Chem. 30, 709 (2012)CrossRefGoogle Scholar
  24. 24.
    G. Mohammadi Ziarani, A. Badiei, S. Mousavi, N. Lashgari, A. Shahbazi, Chin. J. Catal. 33, 1832 (2012)CrossRefGoogle Scholar
  25. 25.
    B. Karmakar, A. Nayak, J. Banerji, Tetrahedron Lett. 53, 5004 (2012)CrossRefGoogle Scholar
  26. 26.
    Y. Li, H. Chen, C. Shi, D. Shi, S. Ji, J. Comb. Chem. 12, 231 (2010)CrossRefPubMedGoogle Scholar

Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  1. 1.Department of Chemistry, Science and Research BranchIslamic Azad UniversityTehranIran

Personalised recommendations