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Zr(HSO4)4/SiO2: An effective heterogeneous alternative for one-pot synthesis of β-acetamido ketones

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Abstract

In a one-pot procedure, enolizable ketones reacted with aromatic aldehydes, acetyl chloride and acetonitrile at room temperature in the presence of Zr(HSO4)4/SiO2 to furnish the corresponding β-acetamido ketones in improved yields.

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References

  1. J. Barluenga, A.L. Viado, E. Aguilar, S. Fustero, B. Olano, J. Org. Chem. 58 (1993) 5972.

    CAS  Google Scholar 

  2. D.P. Henderson, M.C. Shelton, I.C. Cotterill, E.J. Toone, J. Org. Chem. 62 (1997) 7910.

    CAS  Google Scholar 

  3. M. Uramoto, K. Kobinata, K. Isono, T. Higashijima, T. Miyazawa, E.E. Jenkins, J. McCloskey, A. Tetrahedron Lett. 21 (1980) 3395.

    CAS  Google Scholar 

  4. H.D. Dakin, R. West, J. Biol. Chem. 78 (1928) 745.

    CAS  Google Scholar 

  5. M.M. Reddy, B. Bhatia, J. Iqbal, Tetrahedron Lett. 36 (1995) 4877.

    CAS  Google Scholar 

  6. D. Bahulayan, S.K. Das, J. Iqbal, J. Org. Chem. 68 (2003) 5735.

    CAS  Google Scholar 

  7. A.T. Khan, L.H. Choudhury, T. Parvin, M. Asif Ali, Tetrahedron Lett. 47 (2006) 8137.

    CAS  Google Scholar 

  8. M.M. Khodaei, A.R. Khosropour, P. Fattahpour, Tetrahedron Lett. 46 (2005) 2105.

    CAS  Google Scholar 

  9. M.M. Heravi, L. Ranjbar, F. Derikvand, F. Bamoharram, Catal. Commun. 8 (2007) 289.

    CAS  Google Scholar 

  10. L. Nagarapu, S. Kantevari, V.N. Cheemalapati, S. Apuri, V. Kumari, J. Mol.Catal. A: Chem. 264 (2006) 22.

    Google Scholar 

  11. M.T. Maghsoodlou, A. Hassankhani, H.R. Shaterian, S.M. Habibi-Khorasani, E. Mosaddegh, Tetrahedron Lett. 48 (2007) 1729.

    CAS  Google Scholar 

  12. B. Das, M. Krishnaiah, K. Laxminarayana, K.R. Reddy, J. Mol. Catal. A: Chem. 270 (2007) 284.

    CAS  Google Scholar 

  13. A.T. Khan, T. Parvin, L.H. Choudhury, Tetrahedron 63 (2007) 5593.

    CAS  Google Scholar 

  14. E. Rafiee, F. Tork, M. Joshaghani, Bioorg. Med. Chem. Lett. 16 (2006) 1221.

    CAS  Google Scholar 

  15. M.M. Heravi, L. Ranjbar, F. Derikvand, F.F. Bamoharram, J. Mol. Catal. A:Chem. 271 (2007) 28.

    CAS  Google Scholar 

  16. E. Rafiee, F. Paknezhad, S. Shahebrahimi, M. Joshaghani, S. Eavani, S. Rashidzadeh, J. Mol. Catal. A: Chem. 282 (2008) 92.

    CAS  Google Scholar 

  17. E. Rafiee, F. Shahbazi, M. Joshaghani, F. Tork. J. Mol. Catal. A: Chem. 242 (2005) 129.

    CAS  Google Scholar 

  18. Z. Mirjafary, H. Saeidian, A. Sadeghi, F. Matloubi Moghaddam, Catal. Commun. 9 (2008) 299.

    CAS  Google Scholar 

  19. M. Heravi, L. Ranjbar, F. Derikvand, F.F. Bamoharram, J. Mol. Catal. A:Chem. 276 (2007) 226.

    CAS  Google Scholar 

  20. G. Pandey, R.P. Singh, A. Garg, V.K. Singh, Tetrahedron Lett. 46 (2005) 2137.

    CAS  Google Scholar 

  21. L. Nagarapu, R. Bantu, R. Puttireddy, Appl. Catal. A: Gen. 332 (2007) 307.

    Google Scholar 

  22. R.P. Bhat, V.P. Raje, V.M. Alexander, S.B. Patil, S.D. Samant, Tetrahedron Lett. 46 (2005) 4801.

    CAS  Google Scholar 

  23. R. Ghosh, S. Maiti, A. Chakraborty, S. Chakraborty, A. K. Mukherjee, Tetrahedron 62 (2006) 4059.

    CAS  Google Scholar 

  24. T.V. Yakaiah, B.P. Lingaiah, G. Venkat Reddy, B. Narsaiah, P. Shanthan Rao, ARKIVOC 13 (2007) 227.

    Google Scholar 

  25. S. Besoluk, M. Kucukislamoglu, M. Nebioglu, M. Zengin, M. Arslan, J. Iran. Chem. Soc. 5 (2008) 62.

    CAS  Google Scholar 

  26. F. Shirini, M.A. Zolfigol, A.-R. Abri, J. Iran. Chem. Soc. 5 (2008) 96.

    CAS  Google Scholar 

  27. A. Bamoniri, B.F. Mirjalili, M.A. Zolfigol, I. Mohammadpoor-Baltork, J. Iran. Chem. Soc. 4 (2007) 332.

    CAS  Google Scholar 

  28. K. Niknam, M.A. Zolfigol, T. Sadabadi, A. Nejati, J. Iran. Chem. Soc. 3 (2006) 318.

    CAS  Google Scholar 

  29. M.A. Zolfigol, M. Bagherzadeh, K. Niknam, F. Shirini, I. Mohammadpoor-Baltork, A. Ghorbani Choghamarani, M. Baghbanzadeh, J. Iran. Chem. Soc. 3 (2006) 73.

    CAS  Google Scholar 

  30. K. Niknam, M.A. Zolfigol, T. Sadabadi, J. Iran. Chem. Soc. 4 (2007) 199.

    CAS  Google Scholar 

  31. A. Bamoniri, M.A. Zolfigol, I. Mohammadpoor-Baltork, B.F. Mirjalili, J. Iran. Chem. Soc. 3 (2006) 85.

    CAS  Google Scholar 

  32. F. Shirini, M.A. Zolfigol, A. Safari,; I. Mohammadpoor-Baltork, B.F. Mirjalili, Tetrahedron Lett. 44 (2003) 7463.

    CAS  Google Scholar 

  33. B.F. Mirjalili, M.A. Zolfigol, A. Bamoniri, N. Sheikhan, J. Chin. Chem. Soc. 53 (2006) 955.

    CAS  Google Scholar 

  34. B.F. Mirjalili, M.A. Zolfigol, A. Bamoniri, M.A. Karimi-Zarchi, Z. Zaghaghi, M. Parvaideh, J. Iran. Chem. Soc. 4 (2007) 340.

    CAS  Google Scholar 

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

    CAS  Google Scholar 

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Mirjalili, B.F., Bamoniri, A., Karimi Zarchi, M.A. et al. Zr(HSO4)4/SiO2: An effective heterogeneous alternative for one-pot synthesis of β-acetamido ketones. JICS 7, 95–99 (2010). https://doi.org/10.1007/BF03245864

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  • DOI: https://doi.org/10.1007/BF03245864

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