Research on Chemical Intermediates

, Volume 40, Issue 1, pp 371–383 | Cite as

Mild preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives with magnetic Fe3O4 nanoparticles coated by (3-aminopropyl)-triethoxysilane as catalyst under ambient and solvent-free conditions

  • Hamid Reza Shaterian
  • Majid Mohammadnia


An efficient, one-pot quantitative procedure for preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives from four-component condensation reaction of hydrazine monohydrate, phthalic anhydride, malononitrile or ethyl cyanoacetate, and aromatic aldehydes in the presence of magnetic Fe3O4 nanoparticles coated by (3-aminopropyl)-triethoxysilane as catalyst under mild, ambient, and solvent-free conditions is described. Simple procedure, high yield, short reaction time, and environmentally benign method are advantages of this protocol. The magnetic Fe3O4 nanoparticles coated by (3-aminopropyl)-triethoxysilane can be recovered and reused several times without loss of activity.


Magnetic properties Four-component reaction Ambient conditions Solvent-free Heterogeneous catalyst 



We are grateful to the University of Sistan and Baluchestan Research Council for partial support of this research.


  1. 1.
    J. Zhu, H. Bienayme, Multicomponent Reactions (Wiley, Weinheim, 2005)CrossRefGoogle Scholar
  2. 2.
    A. Dömling, Chem. Rev. 106, 17–89 (2006)CrossRefGoogle Scholar
  3. 3.
    S. Jimenez-Alonso, H. Chavez, A. Estevez-Braan, A. Ravelo, G. Feresin, A. Tapia, Tetrahedron 64, 8938–8942 (2008)CrossRefGoogle Scholar
  4. 4.
    D.F. Tejedor, G. Tellado, Chem. Soc. Rev. 36, 484–491 (2007)CrossRefGoogle Scholar
  5. 5.
    R.V.A. Orru, M. de Greef, Synthesis 10, 1471–1499 (2003)CrossRefGoogle Scholar
  6. 6.
    L. Weber, Drug. Discov. Today 7, 143–147 (2002)Google Scholar
  7. 7.
    A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39, 3169–3210 (2000)CrossRefGoogle Scholar
  8. 8.
    A. Nefzi, J.M. Ostresh, R.A. Houghten, Chem. Rev. 97, 449–472 (1997)CrossRefGoogle Scholar
  9. 9.
    L.A. Thompson, Curr. Opin. Chem. Biol. 4, 324–337 (2000)CrossRefGoogle Scholar
  10. 10.
    A. Dömling, Curr. Opin. Chem. Biol. 6, 306–313 (2002)CrossRefGoogle Scholar
  11. 11.
    N.K. Terrett, A.S. Bell, D. Brown, P. Ellis, Bioorg. Med. Chem. Lett. 6, 1819–1824 (1996)CrossRefGoogle Scholar
  12. 12.
    J. Elguero, In Comprehensive Heterocyclic Chemistry II, A.R. Katrizky, C.W. Rees, E.F.V. Scriven, Eds. Elsevier-Oxford, 1996Google Scholar
  13. 13.
    S.K. Singh, P.G. Reddy, K.S. Rao, B.B. Lohray, P. Misra, S.A. Rajjak, Y.K. Rao, A. Venkatewarlu, Bioorg. Med. Chem. Lett. 14, 499–504 (2004)CrossRefGoogle Scholar
  14. 14.
    M.J. Genin, C. Biles, B.J. Keiser, S.M. Poppe, S.M. Swaney, W.G. Tarpley, Y. Yagi, D.L. Romero, J. Med. Chem. 43, 1034–1040 (2000)CrossRefGoogle Scholar
  15. 15.
    F. Al’-Assar, K.N. Zelenin, E.E. Lesiovskaya, I.P. Bezhan, B.A. Chakchir, Chem. J. 36, 598–603 (2002)Google Scholar
  16. 16.
    S. Grasso, G. De Sarro, A. De Sarro, N. Micale, M. Zappala, G. Puja, M. Baraldi, C. De micheli, J. Med. Chem. 43, 2851–2856 (2000)CrossRefGoogle Scholar
  17. 17.
    Y. Nomoto, H. Obase, H. Takai, M. Teranishi, J. Nakamura, K. Kubo, Chem. Pharm. Bull. 38, 2179–2183 (1990)CrossRefGoogle Scholar
  18. 18.
    N. Watanabe, Y. Kabasawa, Y. Takase, K. Miyazaki, H. Ishihara, K. Kodama, H. Adachi, J. Med. Chem. 41, 3367–3372 (1998)CrossRefGoogle Scholar
  19. 19.
    H.R. Shaterian, M. Mohammadnia, F. Moradi, J. Mol. Liq. 172, 88–92 (2012)CrossRefGoogle Scholar
  20. 20.
    H.R. Shaterian, M. Ranjbar, K. Azizi, J. Mol. Liq. 162, 95–99 (2011)CrossRefGoogle Scholar
  21. 21.
    H.R. Shaterian, M. Ranjbar, J. Mol. Liq. 160, 40–49 (2011)CrossRefGoogle Scholar
  22. 22.
    M.Z. Kassaee, H. Masrouri, F. Movahedi, Appl. Catal. A Gen. 395, 28–33 (2011)CrossRefGoogle Scholar
  23. 23.
    R. Ghahremanzadeh, G.I. Shakibaei, A. Bazgir, Synlett 8, 1129–1132 (2008)Google Scholar
  24. 24.
    M.R. Nabid, S.J. Tabatabaie, R. Gahremanzadeh, A. Bazgir, Ultrason. SonoChem. 17, 159–161 (2010)CrossRefGoogle Scholar
  25. 25.
    D.S. Raghuvanshi, K.N. Singh, Tetrahedron Lett. 52, 5702–5705 (2011)CrossRefGoogle Scholar
  26. 26.
    A.Z.A. Azizi Elassar, Y.M. Elkholy, M.H. Elanagdi, Pharmazie 51, 714–716 (1996)Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2012

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of SciencesUniversity of Sistan and BaluchestanZahedanIran

Personalised recommendations