Advertisement

Journal of the Iranian Chemical Society

, Volume 6, Issue 4, pp 710–714 | Cite as

Coumarin synthesis via Knoevenagel condensation reaction in 1,1,3,3-N,N,N′,N′-tetramethylguanidinium trifluoroacetate ionic liquid

  • A. ShaabaniEmail author
  • R. Ghadari
  • A. Rahmati
  • A. H. Rezayan
Article

Abstract

Coumarin derivatives were synthesized in relatively high yields via Knoevenagel condensation reaction of an ortho-hydroxyaryl aldehyde and an activated β-dicarbonyl C-H acid in the presence of a recyclable ionic liquid 1,1,3,3-N,N,N′,N′-tetramethylguanidinium trifluoroacetate under either classical heating conditions or using microwave irradiation. Application of microwave irradiation decreased the required time by a factor of about 200. The ionic liquid could be recycled several times without loss of efficiency with regards to the reaction times and yields.

Keywords

Coumarin Microwave irradiation β-Dicarbonyl C-H acid Ionic liquid 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. [1]
    J.J. Yourick, R.L. Bronaugh, J. Appl. Toxicol. 17 (1997) 153.Google Scholar
  2. [2]
    R. O’Kennedy, R.D. Thornes, Coumarins: Biology, Applications, and Mode of Action, John Wiley & Sons, New York, 1997.Google Scholar
  3. [3]
    B.E. Nielson, V.E. Heywood in the Biology and Chemistry of the Umbelliferae, Academic Press, London, 1971.Google Scholar
  4. [4]
    R.D.H. Murray, J. Mendez, S.A. Brown, The Natural Coumarins, Occurrence, Chemistry and Biochemistry, John Wiely & Sons, New York, 1982.Google Scholar
  5. [5]
    H. Yamazaki, M. Tanaka, T. Shimada, J. Chromatogr. B 721 (1999) 13.Google Scholar
  6. [6]
    M.E.F. Izquierdo, J.Q. Granados, V.M. Mir, M.C.L. Martinez, Food Chem. 70 (2000) 251.Google Scholar
  7. [7]
    S.R. Trenor, A.R. Shultz, B.J. Love, T.E. Long, Chem. Rev. 104 (2004) 3059.Google Scholar
  8. [8]
    S.W. Park, B.S. Seo, E.H. Kim, D.H. Kim, K.J. Paeng, J. Forensic Sci. 41 (1996) 685.Google Scholar
  9. [9]
    E. Knoevenagel, Ber. Dtsch. Chem. Ges Brelin, 37 (1904) 4461.Google Scholar
  10. [10]
    A.M. Song, X.B. Wang, K.S. Lam, Tetrahedron Lett. 41 (2003) 1775.Google Scholar
  11. [11]
    H. von Pechmann, C. Duisberg, Chem. Ber. 37 (1884) 929.Google Scholar
  12. [12]
    R.L. Shriner, Org. React. 1 (1942) 1.Google Scholar
  13. [13]
    N.S. Narasimahan, R.S. Mali, M.V. Barve, Synthesis, (1979) 906.Google Scholar
  14. [14]
    Yavari, R. Hekmat-Shoar, A. Zonouzi, Tetrahedron Lett. 39 (1998) 2391.Google Scholar
  15. [15]
    F.F. Ye, J.R. Gao, W.J. Sheng, J.H. Jia, Dyes Pigments 77 (2008) 556.Google Scholar
  16. [16]
    J. Oyamada, T. Kitamura, Tetrahedron 62 (2006) 6918.Google Scholar
  17. [17]
    M. Maheswara, V. Siddaiah, G.L.V. Damu, Y.K. Rao, C.V. Rao, J. Mol. Catal. A 255 (2006) 49.Google Scholar
  18. [18]
    T. Welton, Chem. Rev. 99 (1999) 2071.Google Scholar
  19. [19]
    P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 39 (2000) 3772.Google Scholar
  20. [20]
    R. Sheldon, Chem. Commun. (2001) 2399.Google Scholar
  21. [21]
    A. Shaabani, A. Rahmati, Cat. Lett. 100 (2005) 177.Google Scholar
  22. [22]
    A. Shaabani, A. Rahmati, S. Naderi, Bioorg. Med. Chem. Lett. 15 (2005) 5553.Google Scholar
  23. [23]
    A. Shaabani, A.H. Rezayan, J. Porphyr. Phthalocya. 9 (2005) 617.Google Scholar
  24. [24]
    A. Shaabani, E. Soleimani, A. Maleki, Tetrahedron Lett. 47 (2006) 3031.Google Scholar
  25. [25]
    A. Shaabani, A. Sarvary, A. Rahmati, A.H. Rezayan, Lett. Org. Chem. 4 (2007) 68.Google Scholar
  26. [26]
    A. Shaabani, E. Farhangi, A. Rahmati, Appl. Catal. A 14 (2008) 338.Google Scholar
  27. [27]
    A. Shaabani, E. Soleimani, A.H. Rezayan, A. Sarvari, Org. Lett. 10 (2008) 2581.Google Scholar
  28. [28]
    A. Shaabani, S. Samadi, Z. Badri, A. Rahmati, Cat. Lett. 104 (2005) 39.Google Scholar
  29. [29]
    N.M.M. Mateus, L.C. Branco, N.M.T. Lourenco, C.A.M. Afonso, Green Chem. 5 (2003) 347.Google Scholar
  30. [30]
    F. Bigi, L. Chesini, R. Maggi, G. Sartori, J. Org. Chem. 64 (1999) 1033.Google Scholar
  31. [31]
    A. Song, X. Wang, K.S. Lam, Tetrahedron Lett. 44 (2003) 1755.Google Scholar

Copyright information

© Iranian Chemical Society 2009

Authors and Affiliations

  • A. Shaabani
    • 1
    Email author
  • R. Ghadari
    • 1
  • A. Rahmati
    • 1
  • A. H. Rezayan
    • 1
  1. 1.Department of ChemistryShahid Beheshti UniversityTehranIran

Personalised recommendations