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Ionic liquid promoted synthesis of bis(indolyl) methanes

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Central European Journal of Chemistry

Abstract

1-benzyl-3-methyl imidazolium hydrogen sulphate [bnmim][HSO4] was found to be an effective catalyst for the condensation reaction of indoles and derivatives with benzaldehydes in microwave irradiation with lower reaction time and higher yields to give bis(indolyl) methanes.

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References

  1. T. Welton, Chem. Rev. 99, 2071 (1999)

    Article  CAS  Google Scholar 

  2. P. Wasserscheid and W. Keim, Angew. Chem. Int. Ed. 39, 3772 (2000)

    Article  CAS  Google Scholar 

  3. R. Sheldon, Chem. Commun. 2399 (2001)

  4. C.O. Kappe, Tetrahedron 49, 6937 (1993) and references cited therein

    Article  CAS  Google Scholar 

  5. J. G. Huddleston, A. E. Visser, W. M. Reichert, H. D. Willauer, G. A. Broker and R. D. Rogers, Green Chem. 3, 156 (2001)

    Article  CAS  Google Scholar 

  6. S. Lee, J. H. Park, J. Kang and J. K. Lee, Chem. Commun. 1698 (2001)

  7. S. Csihony, C. Fischmeister, C. Bruneau, I. T. Horvath and P. H. Dixneuf, New J. Chem. 11, 1667 (2002)

    Article  Google Scholar 

  8. (a) T. Fischer, A. Sethi, T. Welton, J. Woolf, Tetrahedron Lett. 40, 793 (1999); (b) Z. Baan, Z. Finta, G. Keglevich and I. Hermecz, Tetrahedron Lett. 46, 6203 (2005)

  9. A. Agarwal, N. L. Lancaster, A. R. Sethi and T. Welton, Green Chem. 5, 517 (2002)

    Article  Google Scholar 

  10. R.S. Varma and V.V. Namboodiri, Pure Appl. Chem. 73, 1309 (2001)

    Article  CAS  Google Scholar 

  11. J. Fraga-Dubreuil, J. K. Bourahla, M. Rahmouni, J. P. Bazureau and J. Hamelin, Catal. Commun. 3, 185 (2002)

    Article  CAS  Google Scholar 

  12. M.K. Potdar, S.S. Mohile and M.M. Salunkhe, Tetrahedron Lett. 42, 9285 (2001)

    Article  CAS  Google Scholar 

  13. (a) T. Osawa and M. Namiki, Tetrahedron Lett. 24, 4719 (1983); (b) J.K. Porter, C.W. Bacon, J.D. Robbin, D.S. Himmelsbach and H.C. Higman, J Agric Food Chem. 25, 88 (1977); (c) T.R. Garbe, M. Kobayashi, N. Shimizu, N. Takesue, M. Ozawa and H. Yukawa, J Nat Prod. 63, 596 (2000)

  14. (a) G.W. Gribble, In comprehensive Heterocyclic Chemistry, 2nd ed. (Pergamon Pres: New York, 1996) 202; (b) V. Snieckus, In The Alkaloids (Academic Press: New York, 1998) 11

  15. C. Hong, G.L. Firestone, L.F. Bjeldanes, Biochem. Pharmaco 63, 1085 (2002)

    Article  CAS  Google Scholar 

  16. X. Ge, S. Yannai, G. Rennert, N. Gruener and F. A. Fares, Biochem. Biophys. Res. Commun. 228, 153 (1996)

    Article  CAS  Google Scholar 

  17. (a) C. Lin, J. Hsu, M.N.V. Sastry, H. Fang, Z. Tu, J. Liu and Y. Ching-Fa, Tetrahedron, 61, 11751 (2005); (b) G. Bartoli, M. Bartolacci, M. Bosco, G. Foglia, A. Giuliani, E. Mareantoni, L. Sambri and E. Torregiani, J. Org. Chem. 68, 4594 (2003)

  18. P. Anastas and J. C. Warner, Green chemistry, theory and practice (Oxford, UK, 1998)

  19. L. M. Wang, J. W. Han, H. Tian, J. Sheng, Z. Y. Fan and X. P. Tang, Synlett 337 (2005)

  20. G. V. M. Sharma, J. J. Reddy, P. S. Lakshmi and P. R. Krishna, Tetrahedron Lett. 45, 7729 (2004)

    Article  CAS  Google Scholar 

  21. B. P. Bandgar, S. V. Bettigeri and N. S. Joshi, Monatsh. Chem. 135, 1265 (2004)

    Article  CAS  Google Scholar 

  22. X. L. Feng, C. J. Guan and C. X. Zhao, Synth. Commun. 34, 487 (2004)

    Article  CAS  Google Scholar 

  23. (a) S. J. Ji, M. F. Zhou, D. G. Gu, S. Y. Wang and T. P. Loh, Synlett 2077 (2003); (b) S. J. Ji, M. F. Zhou, D. G. Gu, Z. Q. Jiang and T. P. Loh, Eur. J. Org. Chem. 1584 (2004)

  24. R. R. Nagawade and D. B. Shinde, Acta Chim. Slov. 53, 210 (2006)

    CAS  Google Scholar 

  25. R. R. Nagawade, D. B. Shinde, Bull. Korean Chem. Soc. 26, 12 (2005)

    Google Scholar 

  26. A. Srinivasa, P.P. Varma, V. Hulikal and K. M. Mahadevan, Monatsh. Chem., 39, 111 (2008)

    Article  Google Scholar 

  27. A. Khallafi-Nezhad et. al., Synthesis 617 (2008)

  28. H. Firouzabadi, N. Iranpoor, M. Jafarpour, A. Ghaderi, J. Mol. Catal. A: Chem., 253, 249 (2006)

    Article  CAS  Google Scholar 

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Correspondence to Murlidhar S. Shingare.

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Sadaphal, S.A., Shelke, K.F., Sonar, S.S. et al. Ionic liquid promoted synthesis of bis(indolyl) methanes. cent.eur.j.chem. 6, 622–626 (2008). https://doi.org/10.2478/s11532-008-0069-5

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  • DOI: https://doi.org/10.2478/s11532-008-0069-5

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