Skip to main content
Log in

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

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2
Fig. 1

Similar content being viewed by others

References

  1. J. Zhu, H. Bienayme, Multicomponent Reactions (Wiley, Weinheim, 2005)

    Book  Google Scholar 

  2. A. Dömling, Chem. Rev. 106, 17–89 (2006)

    Article  Google Scholar 

  3. S. Jimenez-Alonso, H. Chavez, A. Estevez-Braan, A. Ravelo, G. Feresin, A. Tapia, Tetrahedron 64, 8938–8942 (2008)

    Article  CAS  Google Scholar 

  4. D.F. Tejedor, G. Tellado, Chem. Soc. Rev. 36, 484–491 (2007)

    Article  CAS  Google Scholar 

  5. R.V.A. Orru, M. de Greef, Synthesis 10, 1471–1499 (2003)

    Article  Google Scholar 

  6. L. Weber, Drug. Discov. Today 7, 143–147 (2002)

    CAS  Google Scholar 

  7. A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39, 3169–3210 (2000)

    Article  Google Scholar 

  8. A. Nefzi, J.M. Ostresh, R.A. Houghten, Chem. Rev. 97, 449–472 (1997)

    Article  CAS  Google Scholar 

  9. L.A. Thompson, Curr. Opin. Chem. Biol. 4, 324–337 (2000)

    Article  CAS  Google Scholar 

  10. A. Dömling, Curr. Opin. Chem. Biol. 6, 306–313 (2002)

    Article  Google Scholar 

  11. N.K. Terrett, A.S. Bell, D. Brown, P. Ellis, Bioorg. Med. Chem. Lett. 6, 1819–1824 (1996)

    Article  Google Scholar 

  12. J. Elguero, In Comprehensive Heterocyclic Chemistry II, A.R. Katrizky, C.W. Rees, E.F.V. Scriven, Eds. Elsevier-Oxford, 1996

  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)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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. 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)

    Article  CAS  Google Scholar 

  17. Y. Nomoto, H. Obase, H. Takai, M. Teranishi, J. Nakamura, K. Kubo, Chem. Pharm. Bull. 38, 2179–2183 (1990)

    Article  CAS  Google Scholar 

  18. N. Watanabe, Y. Kabasawa, Y. Takase, K. Miyazaki, H. Ishihara, K. Kodama, H. Adachi, J. Med. Chem. 41, 3367–3372 (1998)

    Article  CAS  Google Scholar 

  19. H.R. Shaterian, M. Mohammadnia, F. Moradi, J. Mol. Liq. 172, 88–92 (2012)

    Article  CAS  Google Scholar 

  20. H.R. Shaterian, M. Ranjbar, K. Azizi, J. Mol. Liq. 162, 95–99 (2011)

    Article  CAS  Google Scholar 

  21. H.R. Shaterian, M. Ranjbar, J. Mol. Liq. 160, 40–49 (2011)

    Article  CAS  Google Scholar 

  22. M.Z. Kassaee, H. Masrouri, F. Movahedi, Appl. Catal. A Gen. 395, 28–33 (2011)

    Article  CAS  Google Scholar 

  23. R. Ghahremanzadeh, G.I. Shakibaei, A. Bazgir, Synlett 8, 1129–1132 (2008)

    Google Scholar 

  24. M.R. Nabid, S.J. Tabatabaie, R. Gahremanzadeh, A. Bazgir, Ultrason. SonoChem. 17, 159–161 (2010)

    Article  CAS  Google Scholar 

  25. D.S. Raghuvanshi, K.N. Singh, Tetrahedron Lett. 52, 5702–5705 (2011)

    Article  CAS  Google Scholar 

  26. A.Z.A. Azizi Elassar, Y.M. Elkholy, M.H. Elanagdi, Pharmazie 51, 714–716 (1996)

    Google Scholar 

Download references

Acknowledgments

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

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hamid Reza Shaterian.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shaterian, H.R., Mohammadnia, M. 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. Res Chem Intermed 40, 371–383 (2014). https://doi.org/10.1007/s11164-012-0969-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0969-z

Keywords

Navigation