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Green synthesis of benzimidazole derivatives catalyzed by ionic liquid under microwave irradiation

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Abstract

An efficient synthesis of benzimidazole derivatives from o-phenylene diamine and substituted aromatic aldehyde catalyzed by ionic liquid under microwave irradiation was reported. The synthesis conditions were first optimized by single factor experiments. Then, a central composite design combined with response surface methodology was used to study the most effective factors. Optimal conditions were synthesis time 1 h, the reactant/catalyst molar ratio 1:1:0.200, the temperature 50 °C and the microwave power 500 W. Under optimized conditions, the yields of benzimidazole derivatives were 78.55–97.66 %. This method offered the outstanding advantages, such as faster reaction rate, higher yields, recyclable catalyst, environmental friendliness, and simple workup procedure.

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References

  1. M.J. Tebbe, W.A. Spitzer, F. Victor et al., Antirhino/enteroviral vinylacetylene benzimidazoles: a study of their activity and oral plasma levels in mice. J Med Chem 40(24), 3937–3946 (1997)

    Article  CAS  Google Scholar 

  2. M.T. Migawa, J.L. Giradet, J.A. Walker et al., Design, synthesis, and antiviral activity ofα-nucleosides: d-and l-isomers of xylofuranose and (5-deoxyribofuranosyl) benzimidazoles. J Med Chem 41, 1242–1251 (1998)

    Article  CAS  Google Scholar 

  3. I. Tamm, Ribonucleic acid synthesis and influenza virus multiplication. Science 126, 1235–1236 (1957)

    Google Scholar 

  4. Y. Bai, J. Lu, Z. Shi et al., Synthesis of 2, 15-hexadecanedione as a precursor of muscone. Synlett 4, 0544–0546 (2001)

    Google Scholar 

  5. R.W. Middleton, D.G. Wibberley, Synthesis of imidazo [4, 5-b]-and [4, 5-c] pyridines. J Heterocycl Chem 17, 1757–1760 (1980)

    Article  CAS  Google Scholar 

  6. A. Czarny, W.D. Wilson, D.W. Boykin, Synthesis of mono-cationic and dicationic analogs of hoechst 33258. J Heterocycl Chem 33, 1393–1397 (1996)

    Article  CAS  Google Scholar 

  7. H. Sharghi, O. Asemani, Simple and mild procedures for synthesis of benzimidazole derivatives using heterogeneous catalyst systems. J Heterocycl Chem 45, 1293–1298 (2008)

    Article  CAS  Google Scholar 

  8. K. Bahrami, M.M. Khodaei, I. Kavianinia, H2O2/HCl as a new and efficient system for synthesis of 2-substituted benzimidazoles. J Chem Res 12, 783–784 (2006)

    Article  Google Scholar 

  9. L.H. Du, Y.G. Wang, A rapid and efficient synthesis of benzimidazoles using hypervalent iodine as oxidant. Synthesis 5, 675–678 (2007)

    Google Scholar 

  10. N.D. Kokare, J.N. Sangshetti, D.B. Shinde, One-pot efficient synthesis of 2-Aryl-1-arylmethyl-1H-benzimidazoles and 2,4,5-Triaryl-1H-imidazoles using oxalic acid catalyst. Synthesis 18, 2829–2834 (2007)

    Google Scholar 

  11. J. Lu, B.Q. Yang, Y.J. Bai, Microwave irradiation Synthesis of 2-substituted benzimidazoles using PPA as a catalyst under solvent-free conditions. Synth Commun 32, 3703–3709 (2002)

    Article  CAS  Google Scholar 

  12. A.B. Alloum, K. Bougrin, M. Soufiaoui, Synthèse chimiosélective des benzimidazoles sur silice traitée par le chlorure du thionyle. Tetrahedron Lett 44(31), 5935–5937 (2003)

    Article  Google Scholar 

  13. V. Ravi, N. Aayesha, E. Ramu, R. Srinivas, L-Praline catalyzed selective synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles. Tetrahedron Lett 48, 69–72 (2007)

    Article  Google Scholar 

  14. Z.H. Zhang, T.S. Li, J.J. Li, A highly effective sulfamic acid/methanol catalytic system for the synthesis of benzimidazole derivatives at room temperature. Monatshefte für Chemie Chem Mon 138(1), 89–94 (2007)

    Article  CAS  Google Scholar 

  15. M.M. Heravi, M. Tajbakhsh, A.N. Ahmadi et al., Zeolites. Efficient and eco-friendly catalysts for the synthesis of benzimidazoles. Monatshefte für Chemie Chem Mon 137(2), 175–179 (2006)

    Article  CAS  Google Scholar 

  16. T. Welton, Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev 99(8), 2071–2084 (1999)

    Article  CAS  Google Scholar 

  17. J. Yu, H. Wang, Green synthesis of pyrano [2, 3-d]-pyrimidine derivatives in ionic liquids. Synth Commun 35(24), 3133–3140 (2005)

    Article  CAS  Google Scholar 

  18. N. Gupta, G.L. Kad, J. Singh, Acidic ionic liquid [bmim] HSO<sub> 4 </sub>: an efficient catalyst for acetalization and thioacetalization of carbonyl compounds and their subsequent deprotection. Catal Commun 8(9), 1323–1328 (2007)

    Article  CAS  Google Scholar 

  19. L. Perreux, A. Loupy, A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations. Tetrahedron 57(45), 9199–9223 (2001)

    Article  CAS  Google Scholar 

  20. R. Gedye, F. Smith, K. Westaway et al., The use of microwave ovens for rapid organic synthesis. Tetrahedron Lett 27(3), 279–282 (1986)

    Article  CAS  Google Scholar 

  21. P. Lidström, J. Tierney, B. Wathey et al., Microwave assisted organic synthesis—a review. Tetrahedron 57(45), 9225–9283 (2001)

    Article  Google Scholar 

  22. S.M. Landge, B. Török, Synthesis of condensed benzo [N, N]-heterocycles by microwave-assisted solid acid catalysis. Catal Lett 122(3–4), 338–343 (2008)

    Article  CAS  Google Scholar 

  23. S.M. Landge, B. Török, Synthesis of condensed benzo [N, N]-heterocycles by microwave-assisted solid acid catalysis. Catal Lett 122(3–4), 338–343 (2008)

    Article  CAS  Google Scholar 

  24. R. Trivedi, S.K. De, R.A. Gibbs, A convenient one-pot synthesis of 2-substituted benzimidazoles. J Mol Catal A Chem 245(1), 8–11 (2006)

    Article  CAS  Google Scholar 

  25. S.M. Vahdat, M. Khavarpour, S. Baghery, A green and efficient protocol for the synthesis of quinoxaline, benzoxazole and benzimidazole derivatives using heteropolyanion-based ionic liquids: as a recyclable solid catalyst. Comb Chem High Throughput Screen 16(8), 618–627 (2013)

    Article  CAS  Google Scholar 

  26. E. Menteşe, I. Doğan, B. Kahveci, Green protocol: solvent-and catalyst-Free synthesis of benzimidazole derivatives via microwave technique. Chem Heterocycl Compd 49(8), 1136–1140 (2013)

    Article  Google Scholar 

  27. M.D. Rosen, Z.M. Simon, K.T. Tarantino et al., A general method for the synthesis of benzimidazole-4-sulfonamides. Tetrahedron Lett 50(11), 1219–1221 (2009)

    Article  CAS  Google Scholar 

  28. G.R. Jadhav, M.U. Shaikh, R.P. Kale et al., Ammonium metavanadate: a novel catalyst for synthesis of 2-substituted benzimidazole derivatives. Chin Chem Lett 20(3), 292–295 (2009)

    Article  CAS  Google Scholar 

  29. U. Srinivas, C. Srinivas, P. Narender et al., Polyaniline-sulfate salt as an efficient and reusable catalyst for the synthesis of 1, 5-benzodiazepines and 2-phenyl benzimidazoles. Catal Commun 8(1), 107–110 (2007)

    Article  CAS  Google Scholar 

  30. B.C. Raju, N.D. Theja, J.A. Kumar, Efficient and inexpensive synthesis of benzimidazoles and quinoxalines. Synth Commun 39(1), 175–188 (2008)

    Article  Google Scholar 

  31. S.L. Ahnazarova, V.V. Kafarov, A.P. Rep’ev, Experiment optimization in chemistry and chemical engineering [M] (Mir Publishers, Moscow, 1982)

    Google Scholar 

  32. A.I. Khuri, J.A. Cornell, Response surfaces: designs and analyses [M] (CRC Press, Florida, 1996)

    Google Scholar 

Download references

Acknowledgments

The authors gratefully acknowledge the financial supports by Program for Agriculture Science and Technology Achievements Transformation Fund Program (2012GB23600641), Importation of International Advanced Forestry Science and Technology, National Forestry Bureau (2012-4-06).

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Authors and Affiliations

  1. State Engineering Laboratory of Bio-Resource Eco-Utilization, Northeast Forestry University, Harbin, 150040, People’s Republic of China

    Mingcong Qin, Yujie Fu, Xiqing Wang, Yuhang Zhang & Weidong Ma

  2. Engineering Research Center of Forest Bio-Preparation, Ministry of Education, Northeast Forestry University, Harbin, 150040, People’s Republic of China

    Mingcong Qin, Yujie Fu, Xiqing Wang, Yuhang Zhang & Weidong Ma

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  1. Mingcong Qin
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Correspondence to Yujie Fu.

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Qin, M., Fu, Y., Wang, X. et al. Green synthesis of benzimidazole derivatives catalyzed by ionic liquid under microwave irradiation. J IRAN CHEM SOC 11, 1553–1559 (2014). https://doi.org/10.1007/s13738-014-0426-6

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  • DOI: https://doi.org/10.1007/s13738-014-0426-6

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