Skip to main content
SpringerLink
Log in

Knoevenagel condensation in aqueous micellar media using EDAHS as a new Bronsted acidic ionic liquid

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

Abstract

The Knoevenagel condensation between aromatic aldehydes and malononitrile, barbituric acid or 1,3-dimethylbarbituric acid with ethane-1,2-diammonium hydrogen sulfate (EDAHS) in aqueous micellar media, using sodium dodecyl sulfate is described. EDAHS was found to be a highly active and stable Bronsted acidic ionic liquid catalyst under the reaction conditions.

Graphical Abstract

.

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

Scheme 1
Fig. 1
Scheme 2

Similar content being viewed by others

References

  1. G. Jones, Organic reaction, vol. 15 (Wiley, New York, 1967), p. 204

    Google Scholar 

  2. F. Texier-Boullet, A. Foucaud, Tetrahedron Lett. 23, 4927 (1982)

    Article  CAS  Google Scholar 

  3. S. Chalais, P. Laszlo, A. Mathy, Tetrahedron Lett. 26, 4453 (1985)

    Article  CAS  Google Scholar 

  4. F. Liang, Y.J. Pu, T. Kurata, J. Kido, H. Nishide, Polymer 46, 3767 (2005)

    Article  CAS  Google Scholar 

  5. G. Kwak, M. Fujiki, Macromolecules 37, 2021 (2004)

    Article  CAS  Google Scholar 

  6. S.M. Lai, C.P. Ng, R. Martin-Arnada, K.L. Yeung, Microporous Mesoporous Mater. 66, 239 (2003)

    Article  CAS  Google Scholar 

  7. M.M. Heravi, F. Derikvand, M. Haghighi, Kh Bakhtiari, Lett. Org. Chem. 3, 297 (2006)

    Article  CAS  Google Scholar 

  8. J. March, Advanced organic chemistry: reactions, mechanisms, and structure, 4th edn. (Wiley, New York, 1992)

    Google Scholar 

  9. D. Prajapati, K.C. Lekhok, J.S. Sandhu, A.C. Ghosh, J. Chem. Soc. Perkin Trans. 1, 959 (1996)

    Article  Google Scholar 

  10. T.I. Reddy, R.S. Verma, Tetrahedron Lett. 38, 1721 (1997)

    Article  CAS  Google Scholar 

  11. J.R. Harjani, S.J. Nara, M.M. Salunkhe, Tetrahedron Lett. 43, 1127 (2002)

    Article  CAS  Google Scholar 

  12. F.A. Khan, J. Dash, R. Satapathy, S.K. Upadhyaya, Tetrahedron Lett. 45, 3055 (2004)

    Article  CAS  Google Scholar 

  13. Z. Wenfei, L. Jinhua, L. Yanqiu, S. Shoufei, R. Xiaoqian, J. Min, Chin J. Catal. 34, 559 (2013)

    Article  Google Scholar 

  14. A. Rostami, B. Atashkar, H. Gholami, Catal. Commu. 37, 69 (2013)

    Article  CAS  Google Scholar 

  15. W. Hu, Z. Guan, X. Deng, Y.-H. He, Biochimie 94, 656 (2012)

    Article  CAS  Google Scholar 

  16. J.M. Khurana, K. Vij, Tetrahedron Lett. 52, 3666 (2011)

    Article  CAS  Google Scholar 

  17. F.X.L. Xamena, F.G. Cirujano, A. Corma, Microporous Mesoporous Mater. 157, 112 (2012)

    Article  Google Scholar 

  18. K.M. Parida, S. Mallick, P.C. Sahoo, S.K. Rana, Appl. Catal. A Gen. 381, 226 (2010)

    Article  CAS  Google Scholar 

  19. A. Modak, J. Mondal, A. Bhaumik, Appl. Catal. A Gen. 459, 41 (2013)

    Article  CAS  Google Scholar 

  20. B.A. Robichaud, K.G. Liu, Tetrahedron Lett. 52, 6935 (2011)

    Article  CAS  Google Scholar 

  21. S. Ghosh, J. Das, S. Chattopadhyay, Tetrahedron Lett. 52, 2869 (2011)

    Article  CAS  Google Scholar 

  22. Y. Zhang, Y. Zhao, C. Xia, J. Mol. Catal. A Chem. 306, 107 (2009)

    Article  CAS  Google Scholar 

  23. J. Xu, K. Shen, B. Xue, Y.-X. Li, J. Mol. Catal. A Chem. 372, 105 (2013)

    Article  CAS  Google Scholar 

  24. C. Pellerin, Chemistry goes green. Ejournal USA Global Issues. (2005)

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

    Article  CAS  Google Scholar 

  26. J.H. Fendler, E.J. Fendler, Catalysis in micellar and macromolecular systems (Academic Press, London, 1975)

    Google Scholar 

  27. Mixed Surfactant Systems, ed. by P. M. Holland, D. N. Rubingh (American Chemical Society, Washington, 1992)

  28. Structure and Reactivity in Aqueous Solution, ed. by C. J. Cramer, D. G. Truhlar (American Chemical Society, Washington, 1994)

  29. Surfactant-Enhanced Subsurface Remediation, ed. by D. A. Sabatini, R. C. Knox, J. H. Harwell (American Chemical Society, Washington, 1994)

  30. D.M. Vriezema, M.C. Aragonés, J.A.A.W. Elemans, J.J.L.M. Cornelissen, A.E. Rowan, R. Nolte, J.M. Chem. Rev. 105, 1445 (2005)

    Article  CAS  Google Scholar 

  31. L. Chen, M. Zheng, Y. Zhou, H. Liu, H. Jiang, Synth. Commun. 38, 239 (2008)

    Article  CAS  Google Scholar 

  32. J.C. Legeay, J.Y. Goujon, J.J. Vanden Eynde, L. Toupet, J.P. Bazureau, J. Comb. Chem. 8, 829 (2006)

    Article  CAS  Google Scholar 

  33. M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, H.G. Kruger, Z. Asgari, V. Khakyzadeh, M. Kazem-Rostami, J. Org. Chem. 77, 3640 (2012)

    Article  CAS  Google Scholar 

  34. M. Ali Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, A. Zare, S.B. Azimi, Z. Asgari, A. Hasaninejad, C. R. Chimie. 15, 719 (2012)

    Article  Google Scholar 

  35. K. Bahrami, M.M. Khodaei, A. Nejati, Green Chem. 12, 1237 (2010)

    Article  CAS  Google Scholar 

  36. M.M. Khodaei, K. Bahrami, A. Farrokhi, Synth. Commun. 40, 1492 (2010)

    Article  CAS  Google Scholar 

  37. K. Bahrami, M.M. Khodaei, F. Naali, J. Org. Chem. 73, 6835 (2008)

    Article  CAS  Google Scholar 

  38. K. Bahrami, M.M. Khodaei, M. Soheilizad, J. Org. Chem. 74, 9287 (2009)

    Article  CAS  Google Scholar 

  39. K. Bahrami, M.M. Khodaei, M. Sheikh Arabi, J. Org. Chem. 75, 6208 (2010)

    Article  CAS  Google Scholar 

  40. K. Bahrami, M.M. Khodaei, P. Fattahpour, Catal Sci. Technol. 1, 389 (2011)

    Article  CAS  Google Scholar 

  41. P.A. Hassan, S.R. Raghavan, E.W. Kaler, Langmuir 18, 2543 (2002)

    Article  CAS  Google Scholar 

  42. M.L. Deb, P.J. Bhuyan, Tetrahedron Lett. 46, 6453 (2005)

    Article  CAS  Google Scholar 

  43. Q. Liu, H. Ai, Z. Li, Ultrason. Sonochem. 18, 477 (2011)

    Article  CAS  Google Scholar 

  44. M. Gupta, R. Gupta, M. Anand, Beilstein J. Org. Chem. 5, 1 (2009)

    Article  Google Scholar 

  45. D.Q. Shi, J. Chen, Q.Y. Zhuang, X.S. Wang, H.W. Hu, Chin. Chem. Lett. 14, 1242 (2003)

    CAS  Google Scholar 

  46. C. Zhuo, D. Xian, W. Jian-Wei, X. Hui, ISRN Org. Chem. 2011, 1 (2011)

    Article  Google Scholar 

  47. M.M. Heravi, K. Bakhtiari, S. Taheri, H.A. Oskooie, J. Chin. Chem. Soc. 54, 1557 (2007)

    CAS  Google Scholar 

Download references

Acknowledgments

We are thankful to the Razi University Research Council for partial support of this work.

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Razi University, 67149-67346, Kermanshah, Iran

    Kiumars Bahrami, Mohammad M. Khodaei, Nasrin Babajani & Fardin Naali

Authors
  1. Kiumars Bahrami
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mohammad M. Khodaei
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Nasrin Babajani
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Fardin Naali
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Kiumars Bahrami.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 821 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bahrami, K., Khodaei, M.M., Babajani, N. et al. Knoevenagel condensation in aqueous micellar media using EDAHS as a new Bronsted acidic ionic liquid. J IRAN CHEM SOC 11, 1675–1680 (2014). https://doi.org/10.1007/s13738-014-0440-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-014-0440-8

Keywords

Search

Navigation