Journal of the Iranian Chemical Society

, Volume 6, Issue 3, pp 588–593 | Cite as

A highly efficient michael addition of indoles to α,β-unsaturated electron-deficient compounds in acidic SDS micellar media

  • A. A. Jafari
  • F. Moradgholi
  • F. Tamaddon


The Michael addition of indoles to α,β-unsaturated electron deficient compounds was catalyzed efficiently at room temperature in acidic micellar solution of sodium dodecyl sulfate (SDS). The substitution on the indole nucleus occurred exclusively at the 3-position in good to excellent yields, and no N-alkylation products were observed.


Michael addition Indole α,β-Unsaturated electron-deficient compounds Micellar media 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. [1] a)
    P.A. Grieco (Ed.), Organic Synthesis in Water, Blacky Academic and Professional, London, 1998Google Scholar
  2. b).
    C.-J. Li, T.-H. Chan, Organic Reactions in Aqueous Media, John Wiley & Sons, New York, 1997Google Scholar
  3. c).
    P. Anastas, J.C. Warner, Green Chemistry, Theory and Practice, Oxford University Press, Oxford, 1998Google Scholar
  4. d).
    U.M. Lindstrom, Chem. Rev. 102 (2002) 2751Google Scholar
  5. e).
    C.-J. Li, Chem. Rev. 105 (2005) 3095.Google Scholar
  6. [2] a)
    S. Kobayashi, Y. Mori, S. Nogayama, K. Manabe, Green Chem. 1 (1999) 175Google Scholar
  7. b).
    B. Cornils, Angew. Chem., Int. Ed. Engl. 34 (1995) 1575.Google Scholar
  8. [3] a)
    P.M. Holland, D.N. Rubingh (Eds.), Mixed Surfactant Systems, ACS, Washington, DC, 1992Google Scholar
  9. b).
    C.J. Cramer, D.G. Truhlar (Eds.), Structure and Reactivity in Aqueous Solution, ACS, Washington, DC, 1994.Google Scholar
  10. [4] a)
    I.V. Berezin, K. Martinek, A.K. Yatsimirskii, Russ. Chem. Rev. 42 (1973) 787Google Scholar
  11. b).
    T. Dwars, U. Schmidt, C. Fischer, I. Grassert, R. Kempe, R. Frçhlich, K. Drauz, G. Nehme, Angew. Chem., Int. Ed. 37 (1998) 2851Google Scholar
  12. c).
    I. Grassert, U. Schmidt, S. Ziegler, C. Fischer, G. Nehme, Tetrahedron Asymmetry 9 (1998) 4193Google Scholar
  13. d).
    R. Selke, J. Holz, A. Riepe, A. Borner, Chem. Eur. J. 4 (1998) 769Google Scholar
  14. e).
    K. Yonehara, T. Hashizume, K. Mori, K. Ohe, S. Uemura, J. Org. Chem. 64 (1999) 5593Google Scholar
  15. f).
    M.S. Goedheijt, B.E. Hanson, J.N.H. Reek, P. C.J. Kamer, P.W.N.M. van Leeuwen, J. Am. Chem. Soc. 122 (2000) 1650Google Scholar
  16. g).
    H. Firouzabadi, N. Iranpoor, A.A. Jafari, Adv. Synth. Catal. 347 (2005) 655.Google Scholar
  17. [5] a)
    G. Bartoli, M. Bartolacci, M. Bosco, G. Foglia, A. Giuliani, E. Marcantoni, L. Sambri, E. Torregiani, J. Org. Chem. 68 (2003) 4594Google Scholar
  18. b).
    M. Bandini, P.G. Cozzi, M. Giacomini, P. Melchiorre, S. Selva, A.U. Ronchi, J. Org. Chem. 67 (2002) 3700.Google Scholar
  19. [6] a)
    J. Szmuszkovicz, J. Am. Chem. Soc. 79 (1975) 2819Google Scholar
  20. b).
    W.E. Noland, G.M. Christensen, G.L. Sauer, G.G.S. Dutton, J. Am. Chem. Soc. 77 (1955) 456Google Scholar
  21. c).
    Z. Iqbal, A.H. Jackson, K.R.N. Rao, Tetrahedron Lett. 29 (1988) 2577Google Scholar
  22. d).
    G. Sri Hair, M. Nagaraju, M.M. Murthy, Synth. Commun. 38 (2008) 100Google Scholar
  23. e).
    L.T. An, J.P. Zou, L.L. Zhang, Y. Zhang Tetrahedron Lett. 48 (2007) 4297Google Scholar
  24. f).
    N. Azizi, F. Arynasab, M.R. Saidi, Org. Biomol. Chem. (2006) 4275Google Scholar
  25. g).
    W. Zhou, L.W. Xu, L. Yang, P.Q. Zhao, C.G. Xia, J. Mol. Catal. A: Chem. 249 (2006) 129Google Scholar
  26. h).
    D. Gu, S. Ji, H. Wang, Q. Xu, Synth. Commun. 38 (2008) 1212.Google Scholar
  27. [7] a)
    Y. Gu, C. Ogawa, S. Kobayashi Org. Lett. 9 (2007) 175Google Scholar
  28. b).
    K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, A. Khorshidi, J. Mol. Catal. A: Chem. 270 (2007) 112Google Scholar
  29. c).
    R. Tahir, K. Banert, A. Solhy, S. Sebti, J. Mol. Catal. A: Chem. 246 (2006) 39Google Scholar
  30. d).
    H. Firouzabadi, N. Iranpoor, F. Nowrouzi, Chem. Commun. (2005) 789Google Scholar
  31. e).
    Z.P. Zhan, R.F. Yang, K. Lang, Tetrahedron Lett. 46 (2005) 3859Google Scholar
  32. f).
    A.V. Reddy, K. Ravinder, V. Goud, P. Kishnaiah, T.V. Raju, Y. Venkateswarlu, Tetrahedron Lett. 44 (2003) 6257Google Scholar
  33. g).
    M.M. Alam, R. Varala, S.R. Adapa, Tetrahedron Lett. 44 (2003) 5115Google Scholar
  34. h).
    K. Manabe, N. Aoyama, S. Kobayashi, Adv. Synth. Catal. 343 (2001) 174Google Scholar
  35. i).
    J.S. Yadav, S. Abraham, B.V.S. Reddy, G. Sabitha, Synthesis (2001) 2165Google Scholar
  36. j).
    Z.H. Huang, J.P. Zou, W.Q. Jiang, Tetrahedron Lett. 47 (2006) 7965Google Scholar
  37. k).
    H. Firouzabadi, N. Iranpoor, M. Jafarpour, A. Ghaderi, J. Mol. Catal. A: Chem. 252 (2006) 150.Google Scholar
  38. [8]
    H. Firouzabadi, N. Iranpoor, A.A. Jafari, Adv. Synth. Catal. 348 (2006) 434.Google Scholar

Copyright information

© Iranian Chemical Society 2009

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of ScienceYazd UniversityYazdIran

Personalised recommendations