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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

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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.

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References

  1. R.D. Rogers, Ionic Liquids as Green Solvents: Progress and Prospect, American Chemical Society Publication, 2005

    Google Scholar 

  2. K. Mikami, Green Reaction Media in Organic Synthesis; Blackwell Publishing, UK, Oxford, 2005

    Book  Google Scholar 

  3. P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis; Wiley-VCH, Weinheim, 2003

    Google Scholar 

  4. A. Zare, A. Hasaninejad, A.R. Moosavi Zare, A. Parhami, H. Sharghi, A. Khalafi-Nezhad, Can. J. Chem. 85 (2007) 438

    CAS  Google Scholar 

  5. A. Zare, A. Hasaninejad, A. Khalafi-Nezhad, A.R. Moosavi Zare, A. Parhami, ARKIVOC xiii (2007) 105

    Google Scholar 

  6. M. Dabiri, P. Salehi, M. Baghbanzadeh, M. Shakouri, S. Otokesh, T. Ekrami, R. Doosti, J. Iran. Chem. Soc. 4 (2007) 393

    CAS  Google Scholar 

  7. M.M. Mojtahedi, M.S. Abaee, H. Abbasi, J. Iran. Chem. Soc. 3 (2006) 93

    Article  CAS  Google Scholar 

  8. A. Sharifi, M.S. Abaee, M. Mirzaei, R. Salimi, J. Iran. Chem. Soc. 5 (2008) 135

    Article  CAS  Google Scholar 

  9. M.M. Khodaei, A.R. Khosropour, S. Ghaderi, J. Iran. Chem. Soc. 3 (2006) 69

    Article  CAS  Google Scholar 

  10. 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) 461

    CAS  Google Scholar 

  11. A.R. Khosropour, M.M. Khodaei, S. Ghaderi, J. Iran. Chem. Soc. 5 (2008) 407.

    CAS  Google Scholar 

  12. A. Zare, A. Parhami, A.R. Moosavi-Zare, A. Hasaninejad, A. Khalafi-Nezhad, M.H. Beyzavi, Can. J. Chem. 87 (2009) 416

    CAS  Google Scholar 

  13. A. Zare, A.R. Moosavi-Zare, A. Hasaninejad, A. Parhami, A. Khalafi-Nezhad, M.H. Beyzavi, Synth. Commun. 39 (2009) 3156

    CAS  Google Scholar 

  14. J.R. Harjani, S.J. Nara, M.M. Salunkhe, Tetrahedron Lett. 43 (2002) 1127

    CAS  Google Scholar 

  15. V.V. Namboodiri, R.S. Varma, Chem. Commun. (2002) 342

    Google Scholar 

  16. V.R. Koch, L.L. Miller, R.A. Osteryoung, J. Am. Chem. Soc. 98 (1976) 5277

    CAS  Google Scholar 

  17. M. Dabiri, P. Salehi, M. Baghbanzadeh, M. Shakouri, S. Otokesh, T. Ekrami, R. Doosti, J. Iran. Chem. Soc. 4 (2007) 393

    CAS  Google Scholar 

  18. G. Zhao, T. Jiang, H. Gao, B. Han, J. Huang, D. Sun, Green Chem. 6 (2004) 75

    CAS  Google Scholar 

  19. C.J. Adams, M.J. Earle, G. Roberts, K.R. Seddon, Chem. Commun. (1998) 2097

    Google Scholar 

  20. H.-P. Zhu, F. Yang, J. Tang, M.-Y. He, Green Chem. 5 (2003) 38

    CAS  Google Scholar 

  21. H. Tajik, K. Niknam, F. Parsa, J. Iran. Chem. Soc. 6 (2009) 159

    Article  CAS  Google Scholar 

  22. 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) 519

    Article  CAS  Google Scholar 

  23. A. Shaabani, R. Ghaderi, A. Rahmati, A.H. Rezayan, J. Iran. Chem. Soc. 6 (2009) 710.

    Article  CAS  Google Scholar 

  24. For reviews see; P. Salehi, M.A. Zolfigol, F. Shirini, M. Baghbanzadeh. Curr. Org. Chem. 10 (2006) 2171)

    CAS  Google Scholar 

  25. F. Shirini, M.A. Zolfigol, P. Salehi, M. Abedini, Curr. Org. Chem. 12 (2008) 183.

    CAS  Google Scholar 

  26. R. Bloch, Chem. Rev. 98 (1998) 1407

    CAS  Google Scholar 

  27. H. Miyabe, M. Ueda, T. Naito, Synlett (2004) 1140

    Google Scholar 

  28. S. Kobayashi, H. Ishitani, Chem. Rev. 99 (1999) 1069.

    CAS  Google Scholar 

  29. A. Vass, J. Dudas, R.S. Varma, Tetrahedron Lett. 40 (1999) 4951

    CAS  Google Scholar 

  30. S.M. Weinreb, Top. Curr. Chem. 190 (1997) 131

    CAS  Google Scholar 

  31. M. Gohain, Synlett (2003) 2097

    Google Scholar 

  32. D. Enders, U. Reinhold, Tetrahedron: Asymmetr. (1997) 1895.

    Google Scholar 

  33. H.-K. Yim, H.N.C. Wong, J. Org. Chem. 69 (2004) 2892.

    CAS  Google Scholar 

  34. H. Nisikori, R. Yoshihara, A. Hosomi, Synlett (2003) 561.

    Google Scholar 

  35. D.L. Boger, W.L. Corbett, T.T. Curran, A.M. Kasper, J. Am. Chem. Soc. 113 (1991) 1713.

    CAS  Google Scholar 

  36. L.G. Arini, A. Sinclair, P. Szeto, R.A. Stockan, Tetrahedron Lett. 45 (2004) 1589.

  37. X.-T. Zhou, Y.-R. Lin, L.-X. Dai, J. Sun, L.-J. Xia, M.- H. Tang, J. Org. Chem. 64 (1999) 1331.

    CAS  Google Scholar 

  38. M.J. Melnick, S.M. Weinreb, A. Freyer, Tetrahedron Lett. 29 (1988) 3891.

    CAS  Google Scholar 

  39. A. Hasaninejad, H. Sharghi, Phosphorus, Sulfur and Silicon 182 (2007) 873

    CAS  Google Scholar 

  40. B.E. Love, P.S. Raje, T.C. Williams, Synlett (1994) 493

    Google Scholar 

  41. W.B. Jennings, C.J. Lovely, Tetrahedron 47 (1991) 5561

    CAS  Google Scholar 

  42. F.A. Davis, J.M. Kaminski, E.W. Kluger, H.S. Freilich, J. Am. Chem. Soc. 97 (1975) 7085

    CAS  Google Scholar 

  43. 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) 2000

    CAS  Google Scholar 

  44. M. Hosseini-Sarvari, H. Sharghi, S. Ebrahimpourmoghaddam, ARKIVOC xv (2007) 255

    Google Scholar 

  45. A. Hasaninejad, A. Zare, J. Sulfur Chem. 28 (2007) 357

    CAS  Google Scholar 

  46. A. Hasaninejad, A. Zare, H. Sharghi, M. Shekouhy, ARKIVOC xi (2008) 64

    Google Scholar 

  47. A. Khalafi-Nezhad, A. Parhami, A. Zare, A. Nasrolahi Shirazi, A.R. Moosavi Zare, A. Hasaninejad, Can. J. Chem. 86 (2008) 456

    CAS  Google Scholar 

  48. A. Zare, A. Hasaninejad, M. Shekouhy, A.R. Moosavi Zare, Org. Prep. Proced. Int. 40 (2008) 457

    CAS  Google Scholar 

  49. A. Hasaninejad, A. Zare, A.R. Moosavi Zare, A. Parhami, H. Sharghi, A. Khalafi-Nezhad, Phosphorus, Sulfur and Silicon 183 (2008) 2769.

    CAS  Google Scholar 

  50. D.L. Borger, W.L. Corbett, J. Org. Chem. 57 (1992) 4777.

    Google Scholar 

  51. B.M. Trost, C. Marrs, J. Org. Chem. 56 (1991) 6468.

    CAS  Google Scholar 

  52. R. Albrecht, G. Kresze, Chem. Ber. 97 (1964) 483

    CAS  Google Scholar 

  53. R. Albrecht, G. Kresze, Chem. Ber. 98 (1965) 1431

    CAS  Google Scholar 

  54. M.J. Melnick, A.J. Freyer, S.M. Weinreb, Tetrahedron Lett. 29 (1988) 3891

    CAS  Google Scholar 

  55. A.K. McFarlane, G. Thomas, A. Whiting, Tetrahedron Lett. 34 (1993) 2379.

    CAS  Google Scholar 

  56. A.M. Kanazawa, J.-N. Denis, A.E. Greene, J. Org. Chem. 59 (1994) 1238

    CAS  Google Scholar 

  57. J. Sisko, M. Mellinger, P.W. Sheldrake, N.H. Baine, Tetrahedron Lett. 37 (1996) 8113

    CAS  Google Scholar 

  58. F. Chemla, V. Hebbe, J.-F. Normant, Synthesis (2000) 75

    Google Scholar 

  59. Z. Li, X. Ren, P. Wei, H. Wan, Y. Shi, P. Ouyang, Green Chem. 8 (2006) 433.

    CAS  Google Scholar 

  60. J.P. Wolfe, J.E. Ney, Org. Lett. (2003) 4607.

    Google Scholar 

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Authors and Affiliations

  1. Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran

    M. A. Zolfigol, A. Khazaei & A. R. Moosavi-Zare

  2. Department of Chemistry, Payame Noor University (PNU), Iran

    A. Zare

Authors
  1. M. A. Zolfigol
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  2. A. Khazaei
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  3. A. R. Moosavi-Zare
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  4. A. Zare
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Corresponding authors

Correspondence to M. A. Zolfigol or A. Khazaei.

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Zolfigol, M.A., Khazaei, A., Moosavi-Zare, A.R. et al. 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. JICS 7, 646–651 (2010). https://doi.org/10.1007/BF03246053

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  • DOI: https://doi.org/10.1007/BF03246053

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