Journal of the Iranian Chemical Society

, Volume 6, Issue 2, pp 436–442

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

  • M. Bararjanian
  • S. Balalaie
  • B. Movassag
  • A. M. Amani
Article

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.

Keywords

Aqueous media L-Proline Pyrano[2,3-d]pyrimidinone Domino Knoevenagel-cyclocondensation 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. [1]
    M. Eissen, J.O. Metzger, E. Schmidt, U. Schneidewind, Angew. Chem. Int. Ed. Engl. 41 (2002) 414.Google Scholar
  2. [2]a)
    P.A. Grieco, Organic Synthesis in Water, Thomson Science, Glasgow, 1998, pp.1–80, 250-261CrossRefGoogle Scholar
  3. b).
    C.J. Li, Chem. Rev. 93 (1993) 2023Google Scholar
  4. [3]
    G. Kaupp, Angew. Chem. Int. Ed. Engl. 33 (1994) 1452.Google Scholar
  5. [4]
    J.O. Metzger, Angew. Chem. Int. Ed. Engl. 37 (1998) 2975.Google Scholar
  6. [5]
    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. [6]a)
    E.M. Griva, S. Lee, C.W. Siyal, D.S. Duch, C.A. Nichol. J. Med. Chem. 23 (1980) 327Google Scholar
  8. b).
    G.L. Anderson, J.L. Shim, A.D. Broom. J. Org. Chem. 41 (1976) 1095.Google Scholar
  9. [7]
    M.M. Ghorab, A.A.Y. Hassan. Phosphorus, Sulfur, Silicon Related Elem. 141 (1998) 251.Google Scholar
  10. [8]a)
    S. Furuya, T. Ohtaki. Eur. Pat. Appl. EP. 608565, 1994, Chem. Abstr. 121 (1994) 205395Google Scholar
  11. b).
    D. Heber, C. Heers, U. Ravens, Pharmazie 48 (1993) 537.Google Scholar
  12. [9]
    W.J. Coates, Eur. Pat., 351058, 1990, Chem. Abstr. 113 (1990) 40711.Google Scholar
  13. [10]
    N. Kitamura, A. Onishi, Eur. Pat., 163599, 1984, Chem. Abstr. 104 (1984) 186439.Google Scholar
  14. [11]
    J. Davoll, J. Clarke, E.F. Eislager. J. Med. Chem. 15 (1972) 837.Google Scholar
  15. [12]
    V.K. Ahluwalia, R. Batla, A. Khurana, R. Kumar, Indian J. Chem. Sec. B 29 (1990) 1141.Google Scholar
  16. [13]
    E. Kretzschmer, Pharmazie 35 (1980) 253.Google Scholar
  17. [14]
    G. Levitt, US Pat., 4339267, 1982, Chem. Abstr. 98 (1983) 215602g.Google Scholar
  18. [15]
    M.K.A. Ibrahim, M.R.H. El-Moghayar, M.A.F. Sharaf, Indian J. Chem. Sec. B 26 (1987) 216.Google Scholar
  19. [16]
    Y. Gao, S.J. Tu, T. Li, X. Zhang, S. Zhu, F. Fang, D. Shi, Synth. Commun. 34 (2004) 1295.Google Scholar
  20. [17]
    I. Devi, B.S.D. Kumar, P.J. Bhuyan, Tetrahedron Lett. 44 (2003) 8307.Google Scholar
  21. [18]
    V.K. Ahluwalia, R. Kumar, M. Alauddin, C.H. Khanduri, N. Mallikov, Synth. Commun. 20 (1990) 1265.Google Scholar
  22. [19]a)
    S. Balalaie, M. Bararjanian, M.A. Amani, B. Movassagh. Synlett (2006) 263Google Scholar
  23. b).
    S. Abdolmohammadi, S. Balalaie, Tetrahedron Lett. 48 (2007) 3299.Google Scholar
  24. [20]a)
    L.A. Paquette, Encyclopedia of Reagents for Organic Synthesis, John Wiley, Chichester, 1995, p. 430Google Scholar
  25. b).
    B. List, Tetrahedron 58 (2002) 5573Google Scholar
  26. c).
    and references cited therein; B. List, Acc. Chem. Res. 37 (2004) 548Google Scholar
  27. d).
    W. Notz, F. Tanaka, C.F. Barbas, Acc. Chem. Res. 37 (2004) 518Google Scholar
  28. e).
    J. Seayad, B. List Org. Biomol. Chem. 3 (2005) 719.Google Scholar
  29. [21]a)
    D. Enders, M.R.M. Hüttl, C. Grondal, G. Raabe, Nature 441 (2006) 861Google Scholar
  30. b).
    S.J. Miller Acc. Chem. Res. 37 (2004) 601Google Scholar
  31. c).
    A. Berkessel, H. Groeger, Asymmetric Organocatlysis, John Wiley-VCH, Weinheim, 2005.CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2009

Authors and Affiliations

  • M. Bararjanian
    • 1
  • S. Balalaie
    • 1
  • B. Movassag
    • 1
  • A. M. Amani
    • 1
  1. 1.Peptide Chemistry Research GroupK. N. Toosi University of TechnologyTehranIran

Personalised recommendations