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[C6(MIm)2]2W10O32 catalyzed efficient one-pot pseudo-four component synthesis of AT-130 analogues under microwave irradiations

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Abstract

Di[1,6-bis(3-methylimidazolium-1-yl)hexane] decatangstate ([C6(MIm)2]2W10O32) was found to be a novel, powerful and effective catalyst for the preparation of N-benzoylglycine carbamides as derivatives of AT-130 via one-pot multicomponent reaction performed under microwave irradiations. The products were obtained in high to excellent yields, thus providing a unique strategy to the large-scale synthesis of these compounds.

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References

  1. V. Rijckborst, M.J. Sonneveld, H.L.A. Janssen, Aliment. Pharmacol. Ther. 33, 501 (2011)

    Article  CAS  Google Scholar 

  2. T.A. Shamliyan, R. MacDonald, A. Shaukat, B.C. Taylor, J.M. Yuan, J.R. Johnson, J. Tacklind, I. Rutks, R.L. Kane, T.J. Wilt, Ann. Intern. Med. 150, 111 (2009)

    Article  Google Scholar 

  3. M.L. Cuestas, V.L. Mathet, J.R. Oubiña, A. Sosnik, Pharm. Res. 27, 1184 (2010)

    Article  CAS  Google Scholar 

  4. S.J. Matthews, Clin. Ther. 29, 2635 (2007)

    Article  CAS  Google Scholar 

  5. J.J.Y. Sung, J.Y. Lai, S. Zeuzem, W.C. Chow, E.J. Heathcote, R.P. Perrillo, C.L. Brosgart, M.A. Woessner, S.A. Scott, D.F. Gray, S.D. Gardner, J. Hepatol. 48, 728 (2008)

    Article  CAS  Google Scholar 

  6. L.M.M. Wolters, H.G.M. Niesters, B.E. Hansen, M.E. van der Ende, F.P. Kroon, C. Richter, K. Brinkman, P.L. Meenhorst, R.A. de Man, J. Clin. Virol. 24, 173 (2002)

    Article  CAS  Google Scholar 

  7. B.M. Liu, T. Li, J. Xu, X.G. Li, J.P. Dong, P. Yan, J.X. Yang, L. Yan, Z.Y. Gao, W.P. Li, X.W. Sun, Y.H. Wang, X.J. Jiao, C.S. Hou, H. Zhuang, Antiviral Res. 85, 512 (2010)

    Article  CAS  Google Scholar 

  8. P. Wang, D. Naduthambi, R.T. Mosley, C. Niu, P.A. Furman, M.J. Otto, M.J. Sofia, Biorg. Med. Chem. Lett. 21, 4642 (2011)

    Article  CAS  Google Scholar 

  9. W.L. Dong, Z.X. Liu, X.H. Liu, Z.M. Li, W.G. Zhao, Eur. J. Med. Chem. 45, 1919 (2010)

    Article  CAS  Google Scholar 

  10. T. Rajkumar, G. Ranga Rao, J. Chem. Sci. 120, (2008) 587

    Google Scholar 

  11. A. Corma, S. Iborra, F.X.L. Xamena, R. Montόn, J.J. Calvino, C. Prestipino, J. Phys. Chem. C 114, 8828 (2010)

    Article  CAS  Google Scholar 

  12. Q.S. Gao, S.N. Wang, Y. Tang, C. Giordano, Chem. Commun. 48, 260 (2012)

    Article  CAS  Google Scholar 

  13. B.S. Chhikara, R. Chandra, V. Tandon, J. Catal. 230, 436 (2005)

    Article  CAS  Google Scholar 

  14. B. S. Chhikara, S. Tehlan, A. Kumar, Synlett. (2005) 63

  15. L. Liu, C. Chen, X. Hu, T. Mohamood, W. Ma, J. Lin, J. Zhao, New J. Chem. 32, 283 (2008)

    Article  CAS  Google Scholar 

  16. H. Li, Y. Qiao, L. Hua, Z. Hou, B. Feng, Z. Pan, Y. Hu, X. Wang, X. Zhao, Y. Yu, Chem. Cat. Chem. 2, 1165 (2010)

    CAS  Google Scholar 

  17. V.P. Mehta, S.G. Modha, E. Ruijter, K. Van Heck, L. Van Meervelt, C. Pannecouque, J. Bazarini, R.V.A. Orrru, E.D. Eyckent, J. Org. Chem. 76, 2828 (2011)

    Article  CAS  Google Scholar 

  18. M. Rostami, A.R. Khosropour, V. Mirkhani, I. Mohammadpoor-Baltork, M. Moghadam, S. Tangestaninejad, Synlett. 1677 (2011)

  19. M. Rostami, A.R. Khosropour, V. Mirkhani, I. Mohammadpoor-Baltork, M. Moghadam, S. Tangestaninejad, Monatsh. Chem. 142, 1175 (2011)

    Article  CAS  Google Scholar 

  20. M. Rostami, A.R. Khosropour, V. Mirkhani, M. Moghadam, S. Tangestaninejad, I. Mohammadpoor-Baltork, Appl. Catal. A Gen. 397, 27 (2011)

    Article  CAS  Google Scholar 

  21. J. Noei, A.R. Khosropour, Tetrahedron Lett. 54, 9 (2013)

    Article  CAS  Google Scholar 

  22. M. Rostami, A.R. Khosropour, V. Mirkhani, M. Moghadam, S. Tangestaninejad, I. Mohammadpoor-Baltork, C. R. Chim. 14, 869 (2011)

    Article  CAS  Google Scholar 

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Acknowledgments

The authors are grateful to the ‘Center of Excellence of Chemistry of University of Isfahan (CECUI) and also the Research Council of the University of Isfahan for financial support of this work.

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Correspondence to Ahmad R. Khosropour.

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Rostami, M., Khosropour, A.R., Mirkhani, V. et al. [C6(MIm)2]2W10O32 catalyzed efficient one-pot pseudo-four component synthesis of AT-130 analogues under microwave irradiations. J IRAN CHEM SOC 11, 1493–1501 (2014). https://doi.org/10.1007/s13738-014-0420-z

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