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Efficient preparation of acidic ionic liquid-functionalized reduced graphene oxide and its catalytic performance in synthesis of benzimidazole derivatives

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Abstract

This article reports an efficient method with a simple workup for the facile synthesis of benzimidazole derivatives using an acidic ionic liquid covalently supported on graphene sheets. The catalyst was efficiently synthesized and characterized using FTIR, scanning electron microscopy, X-ray photoelectron spectroscopy, energy-dispersive X-ray spectroscopy and X-ray diffraction techniques. The catalytic organic reaction was performed in different conditions. Among the various catalysts, A-FGO is an excellent catalyst in the reaction. A wide variety of aldehydes were used under optimal reaction conditions to synthesis benzimidazole derivatives. The reaction conditions are mild and the workup method is simple as well as giving high yields. All synthesised products were characterised using melting point, FTIR, 1H NMR, 13C NMR and CHN techniques. At the end of the reaction, the catalyst was recovered by a simple filtration, washed with dichloromethane, dried and then reused in successive reactions. Products were obtained at the same purity as in the initial runs. Shorter reaction times, high yields, safer reaction condition, the eco-friendly nature and possible reuse of the catalyst make these methods an efficient contribution to the current processes within the field of benzimidazole derivatives synthesis.

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References

  1. K.S. Novoselov, A.K. Geim, S.V. Morozov, D. Jiang, Y. Zhang, S.V. Dubonos, I.V. Grigorieva, A.A. Firsov, Science 306, 666 (2004)

    Article  CAS  Google Scholar 

  2. R. Sitko, E. Turek, B. Zawisza, E. Malicka, E. Talik, J. Heimann, A. Gagor, B. Feist, R. Wrzalik, Dalton Trans. 42, 5682 (2013)

    Article  CAS  Google Scholar 

  3. J. Albero, H. Garcia, J. Mol. Catal. A Chem. 408, 296 (2015)

    Article  Google Scholar 

  4. M.M. Kadam, K.B. Dhopte, N. Jha, V.G. Gaikar, P.R. Nemade, New J. Chem. 40, 1436 (2016)

    Article  CAS  Google Scholar 

  5. S.M. Islam, A.S. Roy, R.C. Dey, S. Paul, J. Mol. Catal. A Chem. 394, 66 (2014)

    Article  CAS  Google Scholar 

  6. G. Xu, T. Shi, M. Li, F. Yu, Y. Chen, Res. Chem. Intermed. 41, 8499 (2015)

    Article  CAS  Google Scholar 

  7. R. Peng, Y. Wang, W. Tang, Y. Yang, X. Xie, Polymers 5, 847 (2013)

    Article  Google Scholar 

  8. B.G. Choi, H.S. Park, ChemSusChem. 5, 709 (2012)

    Article  CAS  Google Scholar 

  9. X. Qi, K.Y. Pu, H. Li, X. Zhou, S. Wu, Q.L. Fan, B. Liu, F. Boey, W. Huang, H. Zhang, Angew. Chem. Int. Ed. 49, 9426 (2010)

    Article  CAS  Google Scholar 

  10. A.V. Kumar, K.R. Rao, Tetrahedron Lett. 52, 5188 (2011)

    Article  Google Scholar 

  11. D.R. Dreyer, H.P. Jia, C.W. Bielawski, Angew. Chem. 122, 6965 (2010)

    Article  Google Scholar 

  12. J. Pyun, Angew. Chem. Int. Ed. 50, 46 (2011)

    Article  CAS  Google Scholar 

  13. E. Lam, J.H. Chong, E. Majid, Y. Liu, S. Hrapovic, A.C.W. Leung, J.H.T. Luong, Carbon 50, 1033 (2012)

    Article  CAS  Google Scholar 

  14. J. Safari, S.G. Ravandi, S. Ashiri, New J. Chem. 40, 512 (2016)

    Article  CAS  Google Scholar 

  15. J.F. Blandez, I.E. Adell, A. Primo, M. Alvaro, H. García, J. Mol. Catal. A Chem. 412, 13 (2016)

    Article  CAS  Google Scholar 

  16. L.F. García, M. Blanco, C. Blanco, P. Álvarez, M. Granda, R. Santamaría, R. Menéndez, J. Mol. Catal. A Chem. 416, 140 (2016)

    Article  Google Scholar 

  17. S. Li, S. Guo, H. Yang, G. Gou, R. Ren, J. Li, Z. Dong, J. Jin, J. Ma, J. Hazard. Mater. 270, 11 (2014)

    Article  CAS  Google Scholar 

  18. T.L. Greaves, C.J. Drummond, Chem. Rev. 108, 206 (2008)

    Article  CAS  Google Scholar 

  19. Y. Liu, L. Li, C.X. Xie, Res. Chem. Intermed. 42, 559 (2016)

    Article  CAS  Google Scholar 

  20. F. Dong, C. Jian, G. Kai, S. Qunrong, L. Zuliang, Catal. Lett. 121, 255 (2008)

    Article  Google Scholar 

  21. A. Teimouri, A.N. Chermahini, H. Salavati, L. Ghorbanian, J. Mol. Catal. A Chem. 373, 38 (2013)

    Article  CAS  Google Scholar 

  22. R. Trivedi, S.K. De, R.A. Gibbs, J. Mol. Catal. A Chem. 245, 8 (2006)

    Article  CAS  Google Scholar 

  23. M.N. Esfahani, I.M. Baltork, A.R. Khosropour, M. Moghadam, V. Mirkhani, S. Tangestaninejad, J. Mol. Catal. A Chem. 379, 243 (2013)

    Article  Google Scholar 

  24. M.K. Dhinakaran, K. Soundarajanb, T.M. Das, New J. Chem. 38, 2874 (2014)

    Article  CAS  Google Scholar 

  25. M. Taha, N.H. Ismail, S. Imran, M. Selvaraj, H. Rashwan, F.U. Farhanah, F. Rahim, K.S. Kesavanarayanan, M. Ali, Bioorg. Chem. 61, 36 (2015)

    Article  CAS  Google Scholar 

  26. Y.M. Yan, Y. Rao, M.W. Ding, J. Org. Chem. 81, 1263 (2016)

    Article  CAS  Google Scholar 

  27. M.A. Chari, D. Shobha, T. Sasaki, Tetrahedron Lett. 52, 5575 (2011)

    Article  Google Scholar 

  28. M. Jafarpour, A. Rezaeifard, M. Ghahramaninezhad, T. Tabibi, New J. Chem. 37, 2087 (2013)

    Article  CAS  Google Scholar 

  29. W.S. Hummers, R.E. Offeman, J. Am. Chem. Soc. 80, 1339 (1958)

    Article  CAS  Google Scholar 

  30. S. Stankovich, D.A. Dikin, R.D. Piner, K.A. Kohlhaas, A. Kleinhammes, Y. Jia, Y. Wu, S.T. Nguyen, R.S. Ruoff, Carbon 45, 1558 (2007)

    Article  CAS  Google Scholar 

  31. W. Yan, Y. Huang, Y. Xu, L. Huang, Y. Chen, J. Nanosci. Nanotechnol. 12, 2270 (2012)

    Article  CAS  Google Scholar 

  32. G. Liu, S. Gui, H. Zhou, F. Zeng, Y. Zhou, H. Ye, Dalton Trans. 43, 6977 (2014)

    Article  CAS  Google Scholar 

  33. M. Liu, G. Liu, Y. Zhou, K. Han, H. Ye, J. Mol. Catal. A Chem. 408, 85 (2015)

    Article  CAS  Google Scholar 

  34. Y. Zhu, S. Murali, W. Cai, X. Li, J.W. Suk, J.R. Potts, R.S. Ruoff, Adv. Mater. 22, 3906 (2010)

    Article  CAS  Google Scholar 

  35. A. Dimiev, D.V. Kosynkin, L.B. Alemany, P. Chaguine, J.M. Tour, J. Am. Chem. Soc. 134, 2815 (2012)

    Article  CAS  Google Scholar 

  36. E.V. Alonso, M.T.S. Cordero, A.G.D. Torres, J.M.C. Pavón, Anal. Bioanal. Chem. 385, 1178 (2006)

    Article  Google Scholar 

  37. W. Liu, K.L. Koh, J. Lu, L. Yang, S. Phua, J. Kong, Z. Chen, X. Lu, J. Mater. Chem. 22, 18395 (2012)

    Article  CAS  Google Scholar 

  38. W. Zheng, R. Tan, S. Yin, Y. Zhang, G. Zhao, Y. Chen, D. Yin, Catal. Sci. Technol. 5, 2092 (2015)

    Article  CAS  Google Scholar 

  39. H.L. Guo, X.F. Wang, Q.Y. Qian, F.B. Wang, X.H. Xia, ACS Nano 3, 2653 (2009)

    Article  CAS  Google Scholar 

  40. H.O. Dogan, D. Ekinci, U. Demir, Surf. Sci. 611, 54 (2013)

    Article  CAS  Google Scholar 

  41. W. Qin, L. Han, H. Bi, J. Jian, X. Wu, P. Gao, Nanoscale 7, 20180 (2015)

    Article  CAS  Google Scholar 

  42. C. Mukhopadhyay, P.K. Tapaswi, Tetrahedron Lett. 49, 6237 (2008)

    Article  CAS  Google Scholar 

  43. F.K. Behbahani, A. Lotfi, Eur. Chem. Bull. 2, 694 (2013)

    CAS  Google Scholar 

  44. M.A.W. Wells, K.A. Ohemeng, V.N. Nguyen, S.F. Spano, M.J. Macielag, H.M. Werblood, B.D. Foleno, G.C. Webb, J.F. Barrett, D.J. Hlasta, Bioorg. Med. Chem. Lett. 11, 1545 (2001)

    Article  Google Scholar 

  45. M.A. Chari, D. Shobha, E.R. Kenawy, S.S. Al-Deyab, B.V.S. Reddy, A. Vinu, Tetrahedron Lett. 51, 5195 (2010)

    Article  CAS  Google Scholar 

  46. H. Sharghi, M.H. Beyzavi, M.M. Doroodmand, Eur. J. Org. Chem. 24, 4126 (2008)

    Article  Google Scholar 

  47. L.S. Gadekar, B.R. Arbad, M.K. Lande, Chin. Chem. Lett. 21, 1053 (2010)

    Article  CAS  Google Scholar 

  48. F.K. Behbahani, P. Ziaei, Chem. Heterocycl. Compd. 48, 1011 (2012)

    Article  CAS  Google Scholar 

  49. A.B. Allouma, K. Bougrinb, M. Soufiaouib, Tetrahedron Lett. 44, 5935 (2003)

    Article  Google Scholar 

  50. S.V. Goswami, P.B. Thorat, V.N. Kadam, S.R. Bhusare, J. Chem. Bio. Phy. Sci. 1, 164 (2011)

    CAS  Google Scholar 

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Acknowledgment

The authors wish to gratefully thank the Research Affairs Division at Amir Kabir University of Technology (AUT), Tehran, for financial support.

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Correspondence to E. Kowsari.

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Hanoon, H.D., Kowsari, E., Abdouss, M. et al. Efficient preparation of acidic ionic liquid-functionalized reduced graphene oxide and its catalytic performance in synthesis of benzimidazole derivatives. Res Chem Intermed 43, 1751–1766 (2017). https://doi.org/10.1007/s11164-016-2727-0

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  • DOI: https://doi.org/10.1007/s11164-016-2727-0

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