Skip to main content
Log in

Brønsted-acidic ionic liquid [HO3S(CH2)4MIM][HSO4] as efficient and reusable catalyst for one-pot synthesis of β-acetamido ketones

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Efficient and convenient synthesis of β-acetamido ketones has been achieved by one-pot reaction of acetophenone, aryl aldehydes, acetyl chloride, and acetonitrile in the presence of 3-methyl-1-(4-sulfonylbutyl)imidazolium hydrogensulfate [HO3S(CH2)4MIM][HSO4], a Brønsted-acidic ionic liquid, as a green and reusable catalyst in solvent-free media at room temperature. The catalyst could be recycled and reused without noticeable decrease in catalytic activity.

Graphical Abstract

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

Access this article

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

Instant access to the full article PDF.

Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. Chen L, Huang XJ, Li YQ, Zhou MY, Zheng WJ (2009) Monatsh Chem 140:45

    Article  CAS  Google Scholar 

  2. Zhang P, Zhang ZH (2009) Monatsh Chem 140:199

    Article  CAS  Google Scholar 

  3. Weber L (2002) Drug Discov Today 7:143

    CAS  Google Scholar 

  4. Strubing D, Neumann H, Klaus S, Hubner S, Beller M (2005) Tetrahedron 61:11333

    Article  Google Scholar 

  5. Yu L, Chen B, Huang X (2007) Tetrahedron Lett 48:925

    Article  Google Scholar 

  6. Thompson LA, Ellman JA (1996) Chem Rev 96:555

    Article  CAS  Google Scholar 

  7. Dolle RE, Nelson KH (1996) J Comb Chem 1:235

    Article  Google Scholar 

  8. Casimir JR, Turetta C, Ettouati L, Paris J (1995) Tetrahedron Lett 36:4797

    CAS  Google Scholar 

  9. Godfrey AG, Brooks DA, Hay LA, Peters M, McCarthy JR, Mitchell D (2003) J Org Chem 68:2623

    Article  CAS  Google Scholar 

  10. Dallemagne P, Rault S, Severicourt M, Hassan KM, Robba M (1986) Tetrahedron Lett 27:2607

    Article  CAS  Google Scholar 

  11. Jeffs PW, Redfearn R, Wolfram J (1983) J Org Chem 48:3861

    Article  CAS  Google Scholar 

  12. Paleo MR, Dominguez D, Castedo L (1993) Tetrahedron Lett 34:2369

    Article  CAS  Google Scholar 

  13. Dakin HD, West R (1928) J Biol Chem 78:745

    CAS  Google Scholar 

  14. Buchanan GL (1988) Chem Soc Rev 17:91

    Article  CAS  Google Scholar 

  15. Bhatia B, Reddy MM, Iqbal J (1994) J Chem Res (S) 713

  16. Bahulayan D, Das SK, Iqbal J (2003) J Org Chem 68:5735

    Article  CAS  Google Scholar 

  17. Pandey G, Singh RP, Garg A, Singh VK (2005) Tetrahedron Lett 46:2137

    Article  CAS  Google Scholar 

  18. Khodaei MM, Khosropour AR, Fattahpour P (2005) Tetrahedron Lett 46:2105

    Article  CAS  Google Scholar 

  19. Ghosh R, Maiti S, Chakraborty A (2005) Synlett 115

  20. Ghosh R, Maiti S, Chakraborty A, Chakraborty S, Mukherjee AK (2006) Tetrahedron 62:4059

    Article  CAS  Google Scholar 

  21. Heravi MM, Ranjbar L, Derikvand F, Bamoharram FF (2007) J Mol Catal A Chem 276:226

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  23. Khan AT, Parvin T, Choudhury LH (2007) Tetrahedron 63:5593

    Article  CAS  Google Scholar 

  24. Nagarapu L, Bantu R, Puttireddy R (2007) Appl Catal A 332:304

    Article  CAS  Google Scholar 

  25. Verma AK, Attri P, Chopra V, Tiwari RK, Chandra R (2008) Monatsh Chem 139:1041

    Article  CAS  Google Scholar 

  26. Dabiri M, Salehi P, Baghbanzadeh M (2007) Monatsh Chem 138:1191

    Article  CAS  Google Scholar 

  27. Cole AC, Jensen JL, Ntai I, Tran KLT, Weaver KJ, Forbes DC, James J, Davis H (2002) J Am Chem Soc 124:5962

    Article  CAS  Google Scholar 

  28. Arfan A, Bazureau JP (2005) Org Process Res Dev 9:743

    Article  CAS  Google Scholar 

  29. Qiao K, Yokoyama C (2006) Catal Commun 7:450

    Article  CAS  Google Scholar 

  30. Wasserscheid P, Sesing M, Korth W (2002) Green Chem 4:134

    Article  CAS  Google Scholar 

  31. Davoodnia A, Bakavoli M, Barakouhi Gh, Tavakoli-Hoseini N (2007) Chin Chem Lett 18:1483

    Article  CAS  Google Scholar 

  32. Davoodnia A, Roshani M, Malaeke SH, Bakavoli M (2008) Chin Chem Lett 19:525

    Article  CAS  Google Scholar 

  33. Seifi N, Zahedi-Niaki MH, Barzegari MR, Davoodnia A, Zhiani R, Aghaei Kaju A (2006) J Mol Catal A Chem 260:77

    Article  CAS  Google Scholar 

  34. Wang W, Shao L, Cheng W, Yang J, He M (2008) Catal Commun 9:337

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Abolghasem Davoodnia.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Davoodnia, A., Heravi, M.M., Rezaei-Daghigh, L. et al. Brønsted-acidic ionic liquid [HO3S(CH2)4MIM][HSO4] as efficient and reusable catalyst for one-pot synthesis of β-acetamido ketones. Monatsh Chem 140, 1499–1502 (2009). https://doi.org/10.1007/s00706-009-0193-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-009-0193-8

Keywords

Navigation