Research on Chemical Intermediates

, Volume 39, Issue 8, pp 3877–3885 | Cite as

Mild preparation of chromeno[2,3-d]pyrimidines catalyzed by Brønsted acidic ionic liquids under solvent-free and ambient conditions

Article

Abstract

Brønsted acidic ionic liquids, namely 2-pyrrolidonium hydrogensulfate, N-methyl-2-pyrrolidonium hydrogensulfate, N-methyl-2-pyrrolidonium dihydrogenphosphate, (4-sulfobutyl)tris(4-sulfophenyl)phosphonium hydrogensulfate, triphenyl(propyl-3-sulfonyl)phosphonium toluenesulfonate, l-prolinium sulfate, and l-prolinium nitrate, catalyzed efficient one-pot pseudo-four-component reaction of salicylaldehydes, malononitrile, and secondary amine for preparation of chromeno[2,3-d]pyrimidines under solvent-free conditions at room temperature. The catalysts show environmentally benign character and can be easily prepared, stored, and recovered without obvious significant loss of activity.

Keywords

Ionic liquid Catalyst Solvent free Salicylaldehyde Chromeno[2,3-d]pyrimidine 

References

  1. 1.
    I. Yavari, E. Kowsari, Tetrahedron Lett. 48, 3753 (2007)CrossRefGoogle Scholar
  2. 2.
    P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis (Wiley, Stuttgart, 2002)CrossRefGoogle Scholar
  3. 3.
    M.A.P. Martins, C.P. Frizzo, D.N. Moreira, N. Zanatta, H.G. Bonacorso, Chem. Rev. 108, 2015 (2008)CrossRefGoogle Scholar
  4. 4.
    H. Olivier-Bourbigou, L. Magna, J. Mol. Catal. A 182–183, 419 (2002)Google Scholar
  5. 5.
    A. Mohammad, Green Solvents I: Properties and Applications in Chemistry, ed. by Dr. Inamuddin (Springer, Dordrecht, 2012)Google Scholar
  6. 6.
    A. Mohammad, Green Solvents II: Properties and Applications in Chemistry, ed. by Dr. Inamuddin (Springer, Dordrecht, 2012)Google Scholar
  7. 7.
    C. Yue, D. Fang, L. Liu, T.F. Yi, J. Mol. Liq. 163, 99 (2011)CrossRefGoogle Scholar
  8. 8.
    H.R. Shaterian, M. Arman, F. Rigi, J. Mol. Liq. 158, 145 (2011)CrossRefGoogle Scholar
  9. 9.
    H.R. Shaterian, M. Mohammadnia, F. Moradi, J. Mol. Liq. 172, 88 (2012)CrossRefGoogle Scholar
  10. 10.
    H.R. Shaterian, M. Ranjbar, K. Azizi, J. Mol. Liq. 162, 95 (2011)CrossRefGoogle Scholar
  11. 11.
    H.R. Shaterian, M. Ranjbar, J. Mol. Liq. 160, 40 (2011)CrossRefGoogle Scholar
  12. 12.
    B. Huang, Y. Wang, K. Zhang, Y. Fang, B. Zhou, Chin. J. Catal. 28, 743 (2007)CrossRefGoogle Scholar
  13. 13.
    C. Xie, H. Li, L. Li, S. Yu, F. Liu, J. Hazard. Mater. 151, 847 (2008)CrossRefGoogle Scholar
  14. 14.
    H. Guo, X. Li, J.L. Wang, X.H. Jin, X.F. Lin, Tetrahedron 66, 8300 (2010)CrossRefGoogle Scholar
  15. 15.
    B. Shaohua, C. Lu, J. Yongjun, Y. Jianguo, Chin. J. Chem. 28, 2119 (2010)CrossRefGoogle Scholar
  16. 16.
    C. Cole, J.L. Jensen, I. Nati, K.L.T. Tran, K.J. Weaver, D. Forbes, J. Am. Chem. Soc. 124, 5962 (2002)CrossRefGoogle Scholar
  17. 17.
    G.H. Tao, L. He, N. Sun, Y. Kou, Chem. Commun. 28, 3562 (2005)CrossRefGoogle Scholar
  18. 18.
    R. Ghahremanzadeh, T. Amanpour, A. Bazgir, Tetrahedron Lett. 51, 4202 (2010)CrossRefGoogle Scholar
  19. 19.
    A.K. Gupta, K. Kumari, N. Singh, D.S. Raghuvanshi, K.N. Singh, Tetrahedron Lett. 53, 650 (2012)CrossRefGoogle Scholar
  20. 20.
    A. Zonouzi, M. Biniaz, R. Mirzazadeh, M. Talebi, S.W. Ng, Heterocycles 81, 1271 (2010)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2012

Authors and Affiliations

  1. 1.Department of ChemistryFaculty of Sciences, University of Sistan and BaluchestanZahedanIran

Personalised recommendations