Advertisement

Journal of the Iranian Chemical Society

, Volume 7, Issue 4, pp 895–899 | Cite as

Melamine trisulfonic acid as a new, efficient and reusable catalyst for the solvent free synthesis of coumarins

  • F. Shirini
  • M. A. Zolfigol
  • J. Albadi
Article

Abstract

Melamine trisulfonic acid (MTSA) is easily prepared by the reaction between melamine and neat chlorosulfonic acid at room temperature. This compound can be used as an efficient and recyclable catalyst for the synthesis of coumarins via von Pechmann condensation reaction under solvent-free conditions.

Keywords

Melamine trisulfonic acid Coumarins Pechmann reaction Phenols Solvent-free reaction conditions 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. [1]
    G. Cavettos, G.M. Nano, G. Palmisano, S. Tagliapietra, Tetrahedron: Asymmetry 12 (2001) 707.Google Scholar
  2. [2]
    O. Kayser, H. Kolodziej, Planta Med. 63 (1997) 508.Google Scholar
  3. [3]
    C.J. Wang, Y.J. Hsieh, C.Y. Chu, Y.L. Lim, T.H. Tseng, Cancer Lett. 183 (2002) 163.Google Scholar
  4. [4]
    G.J. Fan, W. Mar, M.K. Park, E. Woot Choi, K. Kim, S. Kim, Bioorg. Med. Chem. Lett. 11 (2001) 2361.Google Scholar
  5. [5]
    S. Kirkiacharian, D.T. Thuy, S. Sicsic, R. Bakhchianian, R. Kurkjian, T. Tonnaire, Il Farmaco 57 (2002) 703.Google Scholar
  6. [6]
    R.O. Kennedy, R.D. Thornes, Coumarins: Biology, Applications and Mode of Action, John Wiley and Sons, Chichester, 1997.Google Scholar
  7. [7]
    M. Maeda, Laser Dyes, Academic Press, New York, 1984.Google Scholar
  8. [8]
    S.M. Sethna, N.M. Shah, Chem. Rev. 36 (1945) 1.Google Scholar
  9. [9]
    H. von Pechmann, C. Duisberg, Chem. Ber. 17 (1884) 929.Google Scholar
  10. [10]
    G. Jones, Org. React. 15 (1967) 204.Google Scholar
  11. [11]
    R.L. Shirner, Org. React. 1 (1942) 1.Google Scholar
  12. [12]
    J.R. Johnson, Org. React. 1 (1942) 210.Google Scholar
  13. [13]
    I. Yavari, R. Hekmat Shoar, A. Zonouzi, Tetrahedron Lett. 39 (1998) 2391.Google Scholar
  14. [14]
    G.A. Cartwright, W. McNab, J. Chem. Res. (S) (1997) 296.Google Scholar
  15. [15]
    A. Robertson, W.F. Sandrock, C.B. Henry, J. Chem. Soc. (1931) 2426.Google Scholar
  16. [16]
    S.M. Sethna, N.M. Shah, R.C. Shah, J. Chem. Soc. (1938) 228.Google Scholar
  17. [17]
    L.L. Woods, J. Sapp, J. Org. Chem. 27 (1962) 3703.Google Scholar
  18. [18]
    D.S. Bose, A.P. Rudradas, M.H. Babu, Tetrahedron Lett. 43 (2002) 9195.Google Scholar
  19. [19]
    S.S. Bahekar, D.B. Shinde, Tetrahedron Lett. 45 (2004) 7999.Google Scholar
  20. [20]
    V.M. Alexander, R.P. Bhat, S.D. Samant, Tetrahedron Lett. 46 (2005) 6957.Google Scholar
  21. [21]
    F. Shirini, K. Marjani, H. Taherpour-Nahzomi, M.A. Zolfigol, Chinese Chem. Lett. 18 (2007) 909.Google Scholar
  22. [22]
    V. Singh, J. Singh, K. Kaur, G.L. Kad, J. Chem. Res. (S) (1997) 58.Google Scholar
  23. [23]
    V. Singh, S. Kaur, V. Sapehiyia, J. Singh, G.L. Kad, Catal. Commun. 6 (2005) 57.Google Scholar
  24. [24]
    M. Maheswara, V. Siddaiah, G.L.V. Damu, Y.K. Rao, C.V. Rao, J. Mol. Catal. A: Chem. 255 (2006) 49.Google Scholar
  25. [25]
    S. Palaniappan, R.C. Shekhar, J. Mol. Catal. A: Chem. 209 (2004) 117.Google Scholar
  26. [26]
    G.V.M. Sharma, J.J. Reddy, P.S. Lakhshmi, P.R. Krishna, Tetrahedron Lett. 46 (2005) 6119.Google Scholar
  27. [27]
    H. Valizadeh, A. Shockravi, Tetrahedron Lett. 46 (2005) 3501.Google Scholar
  28. [28]
    G.P. Romanelli, D. Bennardi, D.M. Ruiz, G. Boronetti, H.J. Thomas, J.C. Autino, Tetrahedron Lett. 45 (2004) 8935.Google Scholar
  29. [29]
    B. Tyagi, M.K. Mishra, R.V. Jasra, J. Mol. Catal. A: Chem. 286 (2008) 41.Google Scholar
  30. [30]
    S. Selvakumar, M. Chidambaram, A.P. Singh, Catal. Commun. 8 (2007) 777.Google Scholar
  31. [31]
    K. Izutsu, H. Yamamoto, Talanta 47 (1998) 1157.Google Scholar
  32. [32]
    F. Shirini, K. Marjani, H. Taherpour Nahzomi, ARKIVOC (2007) 51.Google Scholar
  33. [33]
    P. Salehi, M.A. Zolfigol, F. Shirini, M. Baghbanzadeh, Current Org. Chem. 10 (2006) 2171.Google Scholar
  34. [34]
    F. Shirini, M.A. Zolfigol, P. Salehi, M. Abedini, Current Org. Chem. 12 (2008) 183.Google Scholar
  35. [35]
    E. Kolvari, A. Ghorbani-Choghamarani, P. Salehi, F. Shirini, M.A. Zolfigol, J. Iran. Chem. Soc. 2 (2007) 126.Google Scholar
  36. [36]
    B. Das, K. Venkateswarlu, G. Mahender, H. Holla, J. Chem. Res. (S) (2004) 836.Google Scholar

Copyright information

© Iranian Chemical Society 2010

Authors and Affiliations

  1. 1.Department of Chemistry, College of Sciencethe University of GuilanRashtI. R. Iran
  2. 2.College of ChemistryBu-Ali Sina UniversityHamadanI. R. Iran

Personalised recommendations