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Ionic liquid-mediated Darzens condensation: An environmentally-friendly procedure for the room-temperature synthesis of α,β-epoxy ketones

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Abstract

This room-temperature Darzens condensation of α-chloroacetophenone with various aromatic aldehydes mediated by [bmim][BF4] ionic liquid in the presence of sodium tert-butoxide resulted in the sole formation of good to excellent yields of trans-α,β-epoxy ketones in short time periods. In contrast, tert-butyl 2-chloroacetate underwent Darzens reactions with aldehydes giving mixtures of both cis and trans products with low selectivity. In all reactions, the ionic liquid was recovered and reused in the subsequent reactions without significant loss of activity.

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References

  1. M. Lancaster, Green Chemistry, An Introductory Text, Royal Society of Chemistry, Cambridge, UK, 2002.

    Google Scholar 

  2. Z.L. Shen, S.J. Ji, T.P. Loh, Tetrahedron Lett. 46 (2005) 3137

    CAS  Google Scholar 

  3. J.S. Yadav, B.V.S. Reddy, B. Eshwaraiah, M. Srinivas, P. Vishnumurthy, New J. Chem. 27 (2003) 462.

    CAS  Google Scholar 

  4. M.J. Earle, P.B. McCormac, K.R. Seddon, Green Chem. 1 (1999) 23

    CAS  Google Scholar 

  5. J.G. Huddleston, H.D. Willauer, R.P. Swatloski, A.E. Visser, R.D. Rogers, Chem. Commun. (1998) 1765

  6. J.S. Wilkes, Green Chem. 4 (2002) 73

    CAS  Google Scholar 

  7. C.J. Bradaric, A. Downard, C. Kennedy, A.J. Robertson, Y. Zhou, Green Chem. 5 (2003) 143

    CAS  Google Scholar 

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

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

    CAS  Google Scholar 

  10. H.O. House, Modern Synthetic Reactions, Benjamin: Menlo Park, CA, 1972, p. 670.

    Google Scholar 

  11. S.F. Martin, Synthesis (1979) 633.

  12. Z.T. Wang, L.W. Xu, C.G. Xia, H.Q. Wang, Helv. Chim. Acta 87 (2004) 1958

    CAS  Google Scholar 

  13. S. Arai, Y. Suzuki, K. Tokumaro, T. Shioiri, Tetrahedron Lett. 43 (2002) 833

    CAS  Google Scholar 

  14. S. Arai, T. Shioiri, Tetrahedron Lett. 39 (1998) 2145.

    CAS  Google Scholar 

  15. E.J. Corey, S. Choi, Tetrahedron Lett. 32 (1991) 2857

    CAS  Google Scholar 

  16. V.K. Aggarwal, G. Hynd, W. Picoul, J.L. Vasse, J. Am. Chem. Soc. 124 (2002) 9964

    CAS  Google Scholar 

  17. E.N. Jacobsen, L. Deng, Y. Furukawa, L.E. Martýnez, Tetrahedron 50 (1994) 4323.

    CAS  Google Scholar 

  18. K. Tanaka, R. Shiraishi, Green Chem. 3 (2001) 135

    Google Scholar 

  19. J.P. Jayachandran, T. Balakrishnan, M.L. Wang, J. Mol. Catal. A: Chem. 152 (2000) 91.

    CAS  Google Scholar 

  20. T. Kimachi, H. Kinoshita, K. Kusaka, Y. Takeuchi, M. Aoe, M. Ju-ichi, Synlett (2005) 842

  21. J. Yamawaki, T. Kawate, T. Ando, T. Hanafusa, Bull. Chem. Soc. Jpn. 56 (1983) 1885.

    CAS  Google Scholar 

  22. S. Sano, M. Miyamoto, T. Mitani, Y. Nagao, Heterocycles 68 (2006) 459

    CAS  Google Scholar 

  23. T. Hirashita, K. Kinoshita, H. Yamamura, M. Kaweai, S. Araki, J. Chem. Soc. Perkin Trans. 1 (2000) 825

    Google Scholar 

  24. L.N. Pridgen, A.F. Abdel-Majid, I. Lantos, S. Shilcart, D.S. Eggleston, J. Org. Chem. 58 (1993) 5107.

    CAS  Google Scholar 

  25. A. Sharifi, R. Salimi, M. Mirzaei, M.S. Abaee, Synth. Commun. 37 (2007) 1825.

    CAS  Google Scholar 

  26. A. Sharifi, M. Mirzaei, M.R. Naimi-Jamal, J. Chem. Res. Synop. (2002) 628

  27. A. Sharifi, M.M. Mojtahedi, M.R. Saidi, Tetrahedron Lett. 40 (1999) 1179

    CAS  Google Scholar 

  28. A. Sharifi, M. Mirzaei, M.R. Naimi-Jamal, Monatsh. Chem. 137 (2006) 213

    CAS  Google Scholar 

  29. A. Sharifi, M. Mirzaei, M.R. Naimi-Jamal, Synth. Commun. 35 (2005) 1039

    CAS  Google Scholar 

  30. M.S. Abaee, M.M. Mojtahedi, R. Sharifi, M.M. Zahedi, H. Abbasi, K. Tabar-Heidar, J. Iran. Chem. Soc. 3 (2006) 293.

    CAS  Google Scholar 

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Authors and Affiliations

  1. Organic Chemistry Department, Chemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran

    A. Sharifi, M. S. Abaee, M. Mirzaei & R. Salimi

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  1. A. Sharifi
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  2. M. S. Abaee
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  3. M. Mirzaei
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  4. R. Salimi
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Correspondence to A. Sharifi.

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Sharifi, A., Abaee, M.S., Mirzaei, M. et al. Ionic liquid-mediated Darzens condensation: An environmentally-friendly procedure for the room-temperature synthesis of α,β-epoxy ketones. JICS 5, 135–139 (2008). https://doi.org/10.1007/BF03245826

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  • DOI: https://doi.org/10.1007/BF03245826

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