Skip to main content
SpringerLink
Log in

One-pot synthesis of pyrano[2,3-d]pyrimidinone derivatives catalyzed by L-proline in aqueous media

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

Abstract

An efficient protocol has been developed for the synthesis of various pyrano[2,3-d]pyrimidinones from condensation of aromatic aldehydes, malononitrile and barbituric-or thiobarbituric acid in aqueous ethanol using L-proline as a neutral bifunctional catalyst.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. M. Eissen, J.O. Metzger, E. Schmidt, U. Schneidewind, Angew. Chem. Int. Ed. Engl. 41 (2002) 414.

    CAS  Google Scholar 

  2. P.A. Grieco, Organic Synthesis in Water, Thomson Science, Glasgow, 1998, pp.1–80, 250-261

    Book  Google Scholar 

  3. C.J. Li, Chem. Rev. 93 (1993) 2023

    CAS  Google Scholar 

  4. G. Kaupp, Angew. Chem. Int. Ed. Engl. 33 (1994) 1452.

    Google Scholar 

  5. J.O. Metzger, Angew. Chem. Int. Ed. Engl. 37 (1998) 2975.

    CAS  Google Scholar 

  6. A. Lubineau, J. Auge, Y. Queneau, Synthesis (1994) 741; b) C.J. Li, T.A. Chan, In Organic Reactions in Aqueous Media, John Wiley, Chichesters, 1998; c) C.J. Li, Chem. Rev. 105 (2005) 3095.

    Google Scholar 

  7. E.M. Griva, S. Lee, C.W. Siyal, D.S. Duch, C.A. Nichol. J. Med. Chem. 23 (1980) 327

    Google Scholar 

  8. G.L. Anderson, J.L. Shim, A.D. Broom. J. Org. Chem. 41 (1976) 1095.

    Google Scholar 

  9. M.M. Ghorab, A.A.Y. Hassan. Phosphorus, Sulfur, Silicon Related Elem. 141 (1998) 251.

    CAS  Google Scholar 

  10. S. Furuya, T. Ohtaki. Eur. Pat. Appl. EP. 608565, 1994, Chem. Abstr. 121 (1994) 205395

    Google Scholar 

  11. D. Heber, C. Heers, U. Ravens, Pharmazie 48 (1993) 537.

    CAS  Google Scholar 

  12. W.J. Coates, Eur. Pat., 351058, 1990, Chem. Abstr. 113 (1990) 40711.

    Google Scholar 

  13. N. Kitamura, A. Onishi, Eur. Pat., 163599, 1984, Chem. Abstr. 104 (1984) 186439.

    Google Scholar 

  14. J. Davoll, J. Clarke, E.F. Eislager. J. Med. Chem. 15 (1972) 837.

    CAS  Google Scholar 

  15. V.K. Ahluwalia, R. Batla, A. Khurana, R. Kumar, Indian J. Chem. Sec. B 29 (1990) 1141.

    Google Scholar 

  16. E. Kretzschmer, Pharmazie 35 (1980) 253.

    Google Scholar 

  17. G. Levitt, US Pat., 4339267, 1982, Chem. Abstr. 98 (1983) 215602g.

    Google Scholar 

  18. M.K.A. Ibrahim, M.R.H. El-Moghayar, M.A.F. Sharaf, Indian J. Chem. Sec. B 26 (1987) 216.

    Google Scholar 

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

    CAS  Google Scholar 

  20. I. Devi, B.S.D. Kumar, P.J. Bhuyan, Tetrahedron Lett. 44 (2003) 8307.

    CAS  Google Scholar 

  21. V.K. Ahluwalia, R. Kumar, M. Alauddin, C.H. Khanduri, N. Mallikov, Synth. Commun. 20 (1990) 1265.

    CAS  Google Scholar 

  22. S. Balalaie, M. Bararjanian, M.A. Amani, B. Movassagh. Synlett (2006) 263

    Google Scholar 

  23. S. Abdolmohammadi, S. Balalaie, Tetrahedron Lett. 48 (2007) 3299.

    CAS  Google Scholar 

  24. L.A. Paquette, Encyclopedia of Reagents for Organic Synthesis, John Wiley, Chichester, 1995, p. 430

    Google Scholar 

  25. B. List, Tetrahedron 58 (2002) 5573

    CAS  Google Scholar 

  26. and references cited therein; B. List, Acc. Chem. Res. 37 (2004) 548

    CAS  Google Scholar 

  27. W. Notz, F. Tanaka, C.F. Barbas, Acc. Chem. Res. 37 (2004) 518

    Google Scholar 

  28. J. Seayad, B. List Org. Biomol. Chem. 3 (2005) 719.

    CAS  Google Scholar 

  29. D. Enders, M.R.M. Hüttl, C. Grondal, G. Raabe, Nature 441 (2006) 861

    CAS  Google Scholar 

  30. S.J. Miller Acc. Chem. Res. 37 (2004) 601

    CAS  Google Scholar 

  31. A. Berkessel, H. Groeger, Asymmetric Organocatlysis, John Wiley-VCH, Weinheim, 2005.

    Book  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Peptide Chemistry Research Group, K. N. Toosi University of Technology, P.O. Box, 15875-4416, Tehran, Iran

    M. Bararjanian, S. Balalaie, B. Movassag & A. M. Amani

Authors
  1. M. Bararjanian
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. Balalaie
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. Movassag
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. M. Amani
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. Balalaie.

Additional information

Dedicated to Prof. Abbas Shafiee on the occasion of his 70th birthday

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bararjanian, M., Balalaie, S., Movassag, B. et al. One-pot synthesis of pyrano[2,3-d]pyrimidinone derivatives catalyzed by L-proline in aqueous media. JICS 6, 436–442 (2009). https://doi.org/10.1007/BF03245854

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF03245854

Keywords

Search

Navigation