Skip to main content
Log in

H14[NaP5W30O110] catalyzed one-pot three-component synthesis of dihydropyrano[2,3-c]pyrazole and pyrano[2,3-d]pyrimidine derivatives

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

Abstract

This is a report of an efficient, clean and facile method for the synthesis of 1,4-dihydropyrano[2,3-c] pyrazole and pyrano[2,3- d]pyrimidine derivatives via three-component one-pot condensation of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one or barbituric acid, aldehydes and malononitrile in the presence of a catalytic amount of preyssler type heteropolyacid as a green and reusable catalyst in water or ethanol under refluxing conditions.

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.

Similar content being viewed by others

References

  1. J. Zhu, Eur. J. Org. Chem. (2003) 1133.

    Google Scholar 

  2. R.V.A. Orru, de M. Greef, Synthesis (2003) 1471.

    Google Scholar 

  3. J. Zamocka, E. Misikova, J. Durinda, Pharmazie 46 (1991) 610.

    CAS  Google Scholar 

  4. J.L. Wang, D. Liu, Z.J. Zheng, S. Shan, X. Han, S.M. Srinivasula, C.M. Croce, E.S. Alnemri, Z. Proc. Natl. Acad. Sci. USA 97 (2000) 7124.

    CAS  Google Scholar 

  5. D. Arnetso, W.M. Horspool, N. Martin, A. Ramos, C. Seaone, J. Org. Chem. 54 (1989) 3069.

    Google Scholar 

  6. S. Hatakeyama, N. Ochi, H. Numata, S. Takano, J. Chem. Soc. Chem. Commun. (1988) 1202.

    Google Scholar 

  7. Y. Peng, G. Song, R. Dou, Green Chem. 8 (2006) 573.

    CAS  Google Scholar 

  8. M.H. EL-Nagdi, M.R. H. EL-Maoghayer, G.E.H. ELGemeie, Adv. Heterocyclic Chem. 41 (1987) 319.

    CAS  Google Scholar 

  9. F. Karc, Dyes & Pigments 76 (2008) 97.

    Google Scholar 

  10. S.G. Kuo, L.J. Huang, H. Nakamura, J. Med. Chem. 27 (1984) 539.

    CAS  Google Scholar 

  11. H. Hori, E. Ito, T. Jakta, G. Koyama, H. Umezawa, J. Antibiot. 17 (1964) 96.

    CAS  Google Scholar 

  12. M.E.A. Zaki, Molecules 3 (1998) 71.

    CAS  Google Scholar 

  13. M.H. Elnagdi, M. Ohta, Bull. Chem. Soc. Jap. 46 (1973) 1830.

    CAS  Google Scholar 

  14. J.F. Zhou, S.J. Tu, Y. Gao, M. Ji, Russ. J. Org. Chem. 21 (2001) 742.

    CAS  Google Scholar 

  15. D. Shi, J. Mou, Q. Zhuang, L. Niu, N. Wu, X. Wang, Synth. Commun. 34 (2004) 4557.

    CAS  Google Scholar 

  16. T.S. Jin, A.Q. Wang, Z.L. Cheng, J.-S. Zhang, T.S. Li, Synth. Commun. 35 (2005) 137.

    CAS  Google Scholar 

  17. S.-B. Guo, S.-X. Wang, J.-T. Li, Synth. Commun. 37 (2007) 2111.

    CAS  Google Scholar 

  18. F. Lehmann, M. Holm, S. Laufer J. Comb. Chem. 10 (2008) 364.

    CAS  Google Scholar 

  19. P.A. Grieco, Organic Synthesis in Water, Blackie Academic and Professional, London, 1998.

    Book  Google Scholar 

  20. C.J. Li, T.H. Chan, Organic Reactions in Aqueous Media, John Wiley and Sons, New York, 1997, p. 159.

    Google Scholar 

  21. D.A. Evans, J.S. Tedrow, J.T. Shaw, W.J. Downey, J. Am. Chem. Soc. 124 (2002) 392.

    CAS  Google Scholar 

  22. N. Nakamichi, Y. Kawashita, M. Hayashi, Synthesis (2004) 1015.

    Google Scholar 

  23. M.M. Heravi, V. Zadsirjan, K. Bakhtiari, H.A. Oskooie, F.F. Bamoharram, Catal. Commun. 8 (2007) 315.

    CAS  Google Scholar 

  24. M.H. Alizadeh, H. Razavi, F.F. Bamoharram, M.K. Hassanzadeh, Kinet. Catal. 44 (2003) 524.

    CAS  Google Scholar 

  25. M.M. Heravi, F. Derikvand, A. Haeri, H.A. Oskoie, F.F. Bamoharram, Synth. Commun. 38 (2008) 135.

    CAS  Google Scholar 

  26. M.M. Heravi, F. Derikvand, F.F. Bamoharram, Synth. Commun. 36 (2006) 3109.

    CAS  Google Scholar 

  27. M.M. Heravi, M. Haghighi, F. Derikvand, F.F. Bamoharram, Synth. Commun. 36 (2006) 3103.

    CAS  Google Scholar 

  28. M.M. Heravi, M. Khorasani, F. Derikvand, H.A. Oskooie, F.F. Bamoharram, Synth. Commun. 36 (2006) 2819.

    Google Scholar 

  29. T.S. Jin, R.Q. Zhao, T.S. Li, ARCIVOC xi (2006) 176.

    Google Scholar 

  30. J. Yu, H. Wang, Synth. Commun. 35 (2005) 3133.

    CAS  Google Scholar 

  31. Y. Gao, S. Tu, T. Li, X. Zhang, S. Zhu, F. Fang, D. Shi, Synth. Commun. 34 (2004) 1295.

    CAS  Google Scholar 

  32. T.S. Jin, L.B. Liu, S.J. Tu, Y. Zhao, T.S. Li, J. Chem. Res. 3 (2005) 162.

    Google Scholar 

  33. M.M. Heravi, M. Khorasani, F. Derikvand, H.A. Oskooie, F.F. Bamoharram, Catal. Commun. 8 (2007) 1886.

    CAS  Google Scholar 

  34. T.N. Vasyun’kina, L.M. Bykova, V.N. Plotkin, S.M. Ramsh, Russ. J. Org. Chem. 41 (2005) 742.

    Google Scholar 

  35. H.M.F. Madkour, M.R. Mahmoud, M.H. Nassar, M.M. Habashy, Molecules 5 (2000) 746.

    CAS  Google Scholar 

  36. M.M. Heravi, A. Ghods, K. Bakhtiari, F. Derikvand, Synth. Commun. 40 (2010) 1927 and references cited therein.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to M. M. Heravi or F. Derikvand.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Heravi, M.M., Ghods, A., Derikvand, F. et al. H14[NaP5W30O110] catalyzed one-pot three-component synthesis of dihydropyrano[2,3-c]pyrazole and pyrano[2,3-d]pyrimidine derivatives. JICS 7, 615–620 (2010). https://doi.org/10.1007/BF03246049

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF03246049

Keywords

Navigation