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Journal of the Iranian Chemical Society

, Volume 7, Issue 3, pp 646–651 | Cite as

3-Methyl-1-Sulfonic acid imidazolium chloride as a new, efficient and recyclable catalyst and solvent for the preparation of N-sulfonyl imines at room temperature

  • M. A. Zolfigol
  • A. Khazaei
  • A. R. Moosavi-Zare
  • A. Zare
Article

Abstract

New Brønsted acidic ionic liquid, 3-methyl-1-sulfonic acid imidazolium chloride {[Msim]Cl} was used as an efficient, green and reusable catalyst and solvent for the synthesis of N-sulfonyl imines via the condensation of sulfonamides with aldehydes as well as isatin. The reactions proceeded at room temperature and the title compounds were obtained in high to excellent yields and in relatively short reaction times.

Keywords

Brønsted acidic ionic liquid 3-Methyl-1-sulfonic acid imidazolium chloride {[Msim]Cl} N-Sulfonyl imine Sulfonamide Aldehyde 

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References

  1. [1]a)
    R.D. Rogers, Ionic Liquids as Green Solvents: Progress and Prospect, American Chemical Society Publication, 2005Google Scholar
  2. b).
    K. Mikami, Green Reaction Media in Organic Synthesis; Blackwell Publishing, UK, Oxford, 2005CrossRefGoogle Scholar
  3. c).
    P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis; Wiley-VCH, Weinheim, 2003Google Scholar
  4. d).
    A. Zare, A. Hasaninejad, A.R. Moosavi Zare, A. Parhami, H. Sharghi, A. Khalafi-Nezhad, Can. J. Chem. 85 (2007) 438Google Scholar
  5. e).
    A. Zare, A. Hasaninejad, A. Khalafi-Nezhad, A.R. Moosavi Zare, A. Parhami, ARKIVOC xiii (2007) 105Google Scholar
  6. f).
    M. Dabiri, P. Salehi, M. Baghbanzadeh, M. Shakouri, S. Otokesh, T. Ekrami, R. Doosti, J. Iran. Chem. Soc. 4 (2007) 393Google Scholar
  7. g).
    M.M. Mojtahedi, M.S. Abaee, H. Abbasi, J. Iran. Chem. Soc. 3 (2006) 93CrossRefGoogle Scholar
  8. h).
    A. Sharifi, M.S. Abaee, M. Mirzaei, R. Salimi, J. Iran. Chem. Soc. 5 (2008) 135CrossRefGoogle Scholar
  9. i).
    M.M. Khodaei, A.R. Khosropour, S. Ghaderi, J. Iran. Chem. Soc. 3 (2006) 69CrossRefGoogle Scholar
  10. j).
    A. Zare, A. Hasaninejad, A. Khalafi-Nezhad, A.R. Moosavi-Zare, M.H. Beyzavi, F. Khedri, F. Asadi, N. Hayati and A. Asifi, J. Iran. Chem. Soc. 7 (2010) 461Google Scholar
  11. k).
    A.R. Khosropour, M.M. Khodaei, S. Ghaderi, J. Iran. Chem. Soc. 5 (2008) 407.Google Scholar
  12. [2]a)
    A. Zare, A. Parhami, A.R. Moosavi-Zare, A. Hasaninejad, A. Khalafi-Nezhad, M.H. Beyzavi, Can. J. Chem. 87 (2009) 416Google Scholar
  13. b).
    A. Zare, A.R. Moosavi-Zare, A. Hasaninejad, A. Parhami, A. Khalafi-Nezhad, M.H. Beyzavi, Synth. Commun. 39 (2009) 3156Google Scholar
  14. c).
    J.R. Harjani, S.J. Nara, M.M. Salunkhe, Tetrahedron Lett. 43 (2002) 1127Google Scholar
  15. d).
    V.V. Namboodiri, R.S. Varma, Chem. Commun. (2002) 342Google Scholar
  16. e).
    V.R. Koch, L.L. Miller, R.A. Osteryoung, J. Am. Chem. Soc. 98 (1976) 5277Google Scholar
  17. f).
    M. Dabiri, P. Salehi, M. Baghbanzadeh, M. Shakouri, S. Otokesh, T. Ekrami, R. Doosti, J. Iran. Chem. Soc. 4 (2007) 393Google Scholar
  18. g).
    G. Zhao, T. Jiang, H. Gao, B. Han, J. Huang, D. Sun, Green Chem. 6 (2004) 75Google Scholar
  19. h).
    C.J. Adams, M.J. Earle, G. Roberts, K.R. Seddon, Chem. Commun. (1998) 2097Google Scholar
  20. i).
    H.-P. Zhu, F. Yang, J. Tang, M.-Y. He, Green Chem. 5 (2003) 38Google Scholar
  21. j).
    H. Tajik, K. Niknam, F. Parsa, J. Iran. Chem. Soc. 6 (2009) 159CrossRefGoogle Scholar
  22. k).
    R.S. Bhosale, S.R. Sarda, R.P. Giram, D.S. Raut, S.P. Parwe, S.S. Ardhapure, R.P. Pawar, J. Iran. Chem. Soc. 6 (2009) 519CrossRefGoogle Scholar
  23. l).
    A. Shaabani, R. Ghaderi, A. Rahmati, A.H. Rezayan, J. Iran. Chem. Soc. 6 (2009) 710.CrossRefGoogle Scholar
  24. [3]a)
    For reviews see; P. Salehi, M.A. Zolfigol, F. Shirini, M. Baghbanzadeh. Curr. Org. Chem. 10 (2006) 2171)Google Scholar
  25. b).
    F. Shirini, M.A. Zolfigol, P. Salehi, M. Abedini, Curr. Org. Chem. 12 (2008) 183.Google Scholar
  26. [4]a)
    R. Bloch, Chem. Rev. 98 (1998) 1407Google Scholar
  27. b).
    H. Miyabe, M. Ueda, T. Naito, Synlett (2004) 1140Google Scholar
  28. c).
    S. Kobayashi, H. Ishitani, Chem. Rev. 99 (1999) 1069.Google Scholar
  29. [5]a)
    A. Vass, J. Dudas, R.S. Varma, Tetrahedron Lett. 40 (1999) 4951Google Scholar
  30. b).
    S.M. Weinreb, Top. Curr. Chem. 190 (1997) 131Google Scholar
  31. c).
    M. Gohain, Synlett (2003) 2097Google Scholar
  32. d).
    D. Enders, U. Reinhold, Tetrahedron: Asymmetr. (1997) 1895.Google Scholar
  33. [6]
    H.-K. Yim, H.N.C. Wong, J. Org. Chem. 69 (2004) 2892.Google Scholar
  34. [7]
    H. Nisikori, R. Yoshihara, A. Hosomi, Synlett (2003) 561.Google Scholar
  35. [8]
    D.L. Boger, W.L. Corbett, T.T. Curran, A.M. Kasper, J. Am. Chem. Soc. 113 (1991) 1713.Google Scholar
  36. [9]
    L.G. Arini, A. Sinclair, P. Szeto, R.A. Stockan, Tetrahedron Lett. 45 (2004) 1589.Google Scholar
  37. [10]
    X.-T. Zhou, Y.-R. Lin, L.-X. Dai, J. Sun, L.-J. Xia, M.- H. Tang, J. Org. Chem. 64 (1999) 1331.Google Scholar
  38. [11]
    M.J. Melnick, S.M. Weinreb, A. Freyer, Tetrahedron Lett. 29 (1988) 3891.Google Scholar
  39. [12]a)
    A. Hasaninejad, H. Sharghi, Phosphorus, Sulfur and Silicon 182 (2007) 873Google Scholar
  40. b).
    B.E. Love, P.S. Raje, T.C. Williams, Synlett (1994) 493Google Scholar
  41. c).
    W.B. Jennings, C.J. Lovely, Tetrahedron 47 (1991) 5561Google Scholar
  42. d).
    F.A. Davis, J.M. Kaminski, E.W. Kluger, H.S. Freilich, J. Am. Chem. Soc. 97 (1975) 7085Google Scholar
  43. e).
    F.A. Davis, U. Nadir, E.W. Kluger, T.C. Sedergran, T.W. Panunto, R. Billmers, R. Jenkins, I.J. Turchi, W.H. Watson, J.S. Chen, M. Kimura, J. Am. Chem. Soc. 102 (1980) 2000Google Scholar
  44. f).
    M. Hosseini-Sarvari, H. Sharghi, S. Ebrahimpourmoghaddam, ARKIVOC xv (2007) 255Google Scholar
  45. g).
    A. Hasaninejad, A. Zare, J. Sulfur Chem. 28 (2007) 357Google Scholar
  46. h).
    A. Hasaninejad, A. Zare, H. Sharghi, M. Shekouhy, ARKIVOC xi (2008) 64Google Scholar
  47. i).
    A. Khalafi-Nezhad, A. Parhami, A. Zare, A. Nasrolahi Shirazi, A.R. Moosavi Zare, A. Hasaninejad, Can. J. Chem. 86 (2008) 456Google Scholar
  48. j).
    A. Zare, A. Hasaninejad, M. Shekouhy, A.R. Moosavi Zare, Org. Prep. Proced. Int. 40 (2008) 457Google Scholar
  49. k).
    A. Hasaninejad, A. Zare, A.R. Moosavi Zare, A. Parhami, H. Sharghi, A. Khalafi-Nezhad, Phosphorus, Sulfur and Silicon 183 (2008) 2769.Google Scholar
  50. [13]
    D.L. Borger, W.L. Corbett, J. Org. Chem. 57 (1992) 4777.Google Scholar
  51. [14]
    B.M. Trost, C. Marrs, J. Org. Chem. 56 (1991) 6468.Google Scholar
  52. [15]a)
    R. Albrecht, G. Kresze, Chem. Ber. 97 (1964) 483Google Scholar
  53. b).
    R. Albrecht, G. Kresze, Chem. Ber. 98 (1965) 1431Google Scholar
  54. c).
    M.J. Melnick, A.J. Freyer, S.M. Weinreb, Tetrahedron Lett. 29 (1988) 3891Google Scholar
  55. d).
    A.K. McFarlane, G. Thomas, A. Whiting, Tetrahedron Lett. 34 (1993) 2379.Google Scholar
  56. [16]a)
    A.M. Kanazawa, J.-N. Denis, A.E. Greene, J. Org. Chem. 59 (1994) 1238Google Scholar
  57. b).
    J. Sisko, M. Mellinger, P.W. Sheldrake, N.H. Baine, Tetrahedron Lett. 37 (1996) 8113Google Scholar
  58. c).
    F. Chemla, V. Hebbe, J.-F. Normant, Synthesis (2000) 75Google Scholar
  59. d).
    Z. Li, X. Ren, P. Wei, H. Wan, Y. Shi, P. Ouyang, Green Chem. 8 (2006) 433.Google Scholar
  60. [17]
    J.P. Wolfe, J.E. Ney, Org. Lett. (2003) 4607.Google Scholar

Copyright information

© Iranian Chemical Society 2010

Authors and Affiliations

  1. 1.Faculty of ChemistryBu-Ali Sina UniversityHamedanIran
  2. 2.Department of ChemistryPayame Noor University (PNU)Iran

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