Skip to main content
SpringerLink
Log in

One-pot synthesis of β-acetamido-β-arylpropiophenone employing trifluoroacetic acid as an efficient catalyst

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Trifluoroacetic acid as an efficient catalyst promoting the Dakin–West reaction at ambient temperature is reported for the first time in this paper. A few efficacious auxiliary catalysts were also developed for the Dakin–West reaction. A variety of substituted aryl aldehydes and aryl ketones were found to be applicable to the preparation of some new β-acetamido-β-arylpropiophenones. This procedure has several advantages such as high yields, short reaction time, and smaller amount (0.30 mol%) of catalyst.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1

Similar content being viewed by others

References

  1. J.R. Casimir, C. Turetta, L. Ettouati, J. Paris, Tetrahedron Lett. 36(27), 4797–4800 (1995)

    CAS  Google Scholar 

  2. A. Godfrey, D.A. Brooks, L.A. Hay, M. Peters, J.R. McCarthy, D. Mitchell, J. Org. Chem. 68, 2623–2632 (2003)

    Article  CAS  Google Scholar 

  3. J. Barluenga, A.L. Viado, E. Aguilar, S. Fustero, B. Olano, J. Org. Chem. 58, 5972–5975 (1993)

    Article  CAS  Google Scholar 

  4. D. Enders, M. Moser, G. Geibel, M.C. Laufer, Synthesis 12, 2040–2046 (2004)

    Article  Google Scholar 

  5. M. Mukhopodhyay, B. Bhatia, J. Iqbal, Tetrahedron Lett. 38(6), 1083–1086 (1997)

    Article  Google Scholar 

  6. I. Rao, E.N. Prabhakaran, S.K. Das, J. Iqbal, J. Org. Chem. 68(10), 4079–4082 (2003)

    Article  CAS  Google Scholar 

  7. K. Kobinata, M. Uramoto, M. Nishii, H. Kusakabe, G. Nakamura, K. Isono, Agri. Biol. Chem. 44, 1709–1711 (1980)

    Article  CAS  Google Scholar 

  8. U. Daehn, H. Hagenmaier, H. Hoehne, W.A. Koenig, G. Wolf, H. Zaehner, Arch. Microbiol. 107, 249–256 (1976)

    Article  Google Scholar 

  9. A.K. Tiwari, R.M. Kumbhare, S.B. Agawane, A.Z. Ali, K.V. Kumar, Bioorg. Med. Chem. Lett. 18(14), 4130–4132 (2008)

    Article  CAS  Google Scholar 

  10. P. Dallemagne, S. Rault, M. Severicourt, K.M. Hassan, M. Robba, Tetrahedron Lett. 27(23), 2607–2610 (1986)

    Article  CAS  Google Scholar 

  11. P.W. Jeffs, R. Redfearn, J. Wolfram, J. Org. Chem. 48, 3861–3863 (1983)

    Article  CAS  Google Scholar 

  12. M.R. Paleo, D. Dominguez, L. Castedo, Tetrahedron Lett. 34(14), 2369–2370 (1993)

    Article  CAS  Google Scholar 

  13. B. Bhatia, M.M. Reddy, J. Iqbal, J. Chem. Soc. Chem. Commun. 713–714 (1994)

  14. M.M. Khodaei, A.R. Khosropour, P. Fattahpour, Tetrahedron Lett. 46, 2105–2108 (2005)

    Article  CAS  Google Scholar 

  15. L. Nagarapu, S. Kantevari, V.N. Cheemalapati, S. Apuri, N.V. Kumari, J. Mol. Catal. A Chem. 264, 22–25 (2007)

    Article  CAS  Google Scholar 

  16. M.M. Heravi, L. Ranjbar, F. Derikvand, F.F. Bamoharram, Catal. Commun. 8, 289–291 (2007)

    Article  CAS  Google Scholar 

  17. R. Ghosh, S. Maiti, A. Chakraborty, S. Chakraborty, A.K. MukherJee, Tetrahedron 62, 4059–4064 (2006)

    Article  CAS  Google Scholar 

  18. B. Das, M. Srilatha, B. VeeranJaneyulu, B.R. Rao, Synthesis 5, 0803–0807 (2010)

    Article  Google Scholar 

  19. V.S. Shinu, B. SheeJa, E. Purushothaman, D. Bahulayan, Tetrahedron Lett. 50, 4838–4843 (2009)

    Article  CAS  Google Scholar 

  20. L. Nagarapu, R. Bantu, R. Puttireddy, Appl. Catal. A Gen. 332, 304–309 (2007)

    Article  CAS  Google Scholar 

  21. A. Hassankhani, M.T. Maghsoodlou, S.M. Habibi-Khorassani, H. Hosseini-Mahdiabad, G. Marandi, Arkivoc ii, 134–140 (2008)

    Google Scholar 

  22. D. Bahulayan, S.K. Das, J. Iqbal, J. Org. Chem. 68(14), 5735–5738 (2003)

    Article  CAS  Google Scholar 

  23. A.A. Beushev, V.V. Kon’shin, N.A. Chemeris, M.M. Chemeris, Russ. J. Appl. Chem. 81(10), 1856–1859 (2008)

    Article  CAS  Google Scholar 

  24. C.A. Guy, G.B. Fields, Methods Enzymol. 289, 67–83 (1997)

    Article  CAS  Google Scholar 

  25. V. Cadierno, J. Francos, J. Gimeno, Chem. Commun. 46(23), 4175–4177 (2010)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China

    Xing-Hua Zhang, Li Fan, Jian Liu & Da-Cheng Yang

Authors
  1. Xing-Hua Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Li Fan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jian Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Da-Cheng Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Da-Cheng Yang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zhang, XH., Fan, L., Liu, J. et al. One-pot synthesis of β-acetamido-β-arylpropiophenone employing trifluoroacetic acid as an efficient catalyst. Res Chem Intermed 37, 811–820 (2011). https://doi.org/10.1007/s11164-011-0288-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-011-0288-9

Keywords

Search

Navigation