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Research on Chemical Intermediates

, Volume 39, Issue 3, pp 1101–1108 | Cite as

Brønsted acid ionic liquid [Et3NH][HSO4] as an efficient and reusable catalyst for the synthesis of 2,4,5-triaryl-1H-imidazoles

  • Xiaocui Deng
  • Zhongqiang ZhouEmail author
  • Aiqing Zhang
  • Guangyong Xie
Article

Abstract

A simple and efficient procedure for synthesis of 2,4,5-triaryl-1H-imidazoles by one-pot three-component condensation of aromatic aldehydes, benzil and ammonium acetate under solvent-free conditions using ionic liquid [Et3NH][HSO4] as catalyst is described. The remarkable features of this procedure are high yields, cleaner reaction profiles, use of non-toxic, easily available, cheap, recyclable catalyst, which also has an environmentally benign nature, and simple experimental and work-up procedures.

Keywords

2,4,5-triaryl-1H-imidazole [Et3NH][HSO4Solvent-free Benzil Aromatic aldehydes Ammonium acetate 

Notes

Acknowledgment

We thank the National Natural Science Foundation of China (grant no. 21172269) for financial support.

References

  1. 1.
    G. Fluoret, J. Med. Chem. 13, 843 (1970)CrossRefGoogle Scholar
  2. 2.
    R.N. Brogden, R.C. Heel, T.M. Speight, G.S. Avery, Drugs 16, 387 (1978)CrossRefGoogle Scholar
  3. 3.
    R.W. Brimblecombe, W.A.M. Duncan, G.J. Durant, J.C. Emmett, C.R. Ganellin, M.E. Parsons, J. Int. Med. Res. 3, 86 (1975)Google Scholar
  4. 4.
    W. Hunkeler, H. Mohler, L. Pieri, P. Polc, E.P. Bonetti, R. Cumin, R. Schaffner, W. Haefely, Nature 290, 514 (1981)CrossRefGoogle Scholar
  5. 5.
    S.D. Sharma, P. Hazarika, D. Konwar, Tetrahedron Lett. 49, 2216 (2008)CrossRefGoogle Scholar
  6. 6.
    K.S. Niralwad, B.B. Shingate, M.S. Shingare, J. Heterocycl Chem. 48, 742 (2011)CrossRefGoogle Scholar
  7. 7.
    K.F. Shelke, S.B. Sapkal, G.K. Kakade, B.B. Shingate, M.S. Shingare, Green Chem. Lett. Rev. 3, 27 (2010)CrossRefGoogle Scholar
  8. 8.
    K.F. Shelke, S.B. Sapkal, S.S. Sonar, B.R. Madje, B.B. Shingate, M.S. Shingare, Bull. Korean Chem. Soc. 30, 1057 (2009)CrossRefGoogle Scholar
  9. 9.
    L.W. Wang, Y.H. Wang, H. Tian, Y.F. Yao, J.H. Shao, B. Liu, J. Fluor. Chem. 127, 1570 (2006)CrossRefGoogle Scholar
  10. 10.
    A.A. Mohammadi, M. Mivechi, H. Kefayati, Monatsh. Chem. 139, 935 (2008)CrossRefGoogle Scholar
  11. 11.
    J.N. Sangshetti, N.D. Kokare, S.A. Kotharkar, D.B. Shinde, Chin. Chem. Lett. 19, 762 (2008)CrossRefGoogle Scholar
  12. 12.
    M.M. Heravi, K. Bakhtiari, H.A. Oskooie, S. Taheri, J. Mol. Catal. A 263, 279 (2007)CrossRefGoogle Scholar
  13. 13.
    N.V. Shitole, K.F. Shelke, S.S. Sonar, S.A. Sadaphal, B.B. Shingate, M.S. Shingare, Bull. Korean Chem. Soc. 30, 1963 (2009)CrossRefGoogle Scholar
  14. 14.
    S. Dutta, Acta. Pharm. 60, 229 (2010)CrossRefGoogle Scholar
  15. 15.
    R.S. Joshi, P.G. Mandhane, M.U. Shaikh, R.P. Kale, C.H. Gill, Chin. Chem. Lett. 21, 429 (2010)CrossRefGoogle Scholar
  16. 16.
    X.C. Wang, H.P. Gong, Z.J. Quan, L. Li, H.L. Ye, Chin. Chem. Lett. 20, 44 (2009)CrossRefGoogle Scholar
  17. 17.
    M. Kidwai, P. Mothsra, V. Bansal, R.K. Somvanshi, A.S. Ethayathulla, S. Dey, T.P. Singh, J. Mol. Catal. A 265, 177 (2007)CrossRefGoogle Scholar
  18. 18.
    L. Wang, C. Cai, Monatsh. Chem. 140, 541 (2009)CrossRefGoogle Scholar
  19. 19.
    K. Shelke, G. Kakade, B. Shingate, M. Shingare, Rasayan J. Chem. 1, 489 (2008)Google Scholar
  20. 20.
    S.S. Pandit, S.K. Bhalerao, U.S. Aher, G.L. Adhav, V.U. Pandit, J. Chem. Sci. 123, 421 (2011)CrossRefGoogle Scholar
  21. 21.
    K.F. Shelke, S.B. Sapkal, M.S. Shingare, Chin. Chem. Lett. 20, 283 (2009)CrossRefGoogle Scholar
  22. 22.
    S.V. Bhosale, M.B. Kalyankar, S.V. Nalage, D.S. Bhosale, S.L. Pandhare, T.V. Kotbagi, S.B. Umbarkar, M.K. Dongare, Synth. Commun. 41, 762 (2011)CrossRefGoogle Scholar
  23. 23.
    V.S.V. Satyanarayana, A. Sivakumar, Chem. Pap. 65, 519 (2011)CrossRefGoogle Scholar
  24. 24.
    G.V.M. Sharma, Y. Jyothi, P.S. Lakshmi, Synth. Commun. 36, 2991 (2006)CrossRefGoogle Scholar
  25. 25.
    H.R. Shaterian, M. Ranjbar, K. Azizi, Chin. J. Chem. 29, 1635 (2011)CrossRefGoogle Scholar
  26. 26.
    K. Bahrami, M.M. Khodaei, A. Nejati, Monatsh. Chem. 142, 159 (2011)CrossRefGoogle Scholar
  27. 27.
    J. Safari, S.D. Khalili, M. Rezaei, S.H. Banitaba, F. Meshkani, Monatsh. Chem. 141, 1339 (2010)CrossRefGoogle Scholar
  28. 28.
    L.S. Gadekar, S.R. Mane, S.S. Katkar, B.R. Arbad, M.K. Lande, Cent. Eur. J. Chem. 7, 550 (2009)CrossRefGoogle Scholar
  29. 29.
    C. Kurumurthy, G.S. Kumar, G.M. Reddy, P. Nagender, P.S. Rao, B. Narsaiah, Res. Chem. Intermed. 38, 359 (2012)CrossRefGoogle Scholar
  30. 30.
    F. Shi, Y. Gu, Q. Zhang, Y. Deng, Catal. Surv. Asia 8, 179 (2004)CrossRefGoogle Scholar
  31. 31.
    S.A. Siddiqui, U.G. Narkhede, S.S. Palimkar, T. Daniel, R.J. Lahoti, K.V. Srinivasan, Tetrahedron 61, 3539 (2005)CrossRefGoogle Scholar
  32. 32.
    A. Shaabani, A. Rahmati, B. Aghaaliakbari, J. Safaei-Ghomi, Synth. Commun. 36, 65 (2006)CrossRefGoogle Scholar
  33. 33.
    P. Wasserscheid, R. van Hal, A. Bösmann, Green Chem. 4, 400 (2002)CrossRefGoogle Scholar
  34. 34.
    M.M. Heravi, M. Zakeri, N. Karimi, M. Saeedi, H.A. Oskooie, N. Tavakoli-Hosieni, Synth. Commun. 40, 1998 (2010)CrossRefGoogle Scholar
  35. 35.
    H.R. Shaterian, M. Ranjbar, J. Mol. Liq. 160, 40 (2011)CrossRefGoogle Scholar
  36. 36.
    K. Tanaka, F. Toda, Chem. Rev. 100, 1025 (2000)CrossRefGoogle Scholar
  37. 37.
    T.L. Greaves, C.J. Drummond, Chem. Rev. 108, 206 (2008)CrossRefGoogle Scholar
  38. 38.
    C. Wang, L. Guo, H. Li, Y. Wang, J. Weng, L. Wu, Green Chem. 8, 603 (2006)CrossRefGoogle Scholar
  39. 39.
    A. Rajendran, D. Raghupathy, M. Priyadarshini, Int. J. Chem. Tech. Res. 3, 298 (2011)Google Scholar

Copyright information

© Springer Science+Business Media B.V. 2012

Authors and Affiliations

  • Xiaocui Deng
    • 1
  • Zhongqiang Zhou
    • 1
    Email author
  • Aiqing Zhang
    • 1
  • Guangyong Xie
    • 1
  1. 1.Key Laboratory of Catalysis and Materials Science of the State Ethnic Affairs Commission and Ministry of EducationCollege of Chemistry and Materials Science, South-Central University for NationalitiesWuhanChina

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