Skip to main content
Log in

Poly(4-vinylpyridine)-supported sulfuric acid: an efficient solid acid catalyst for the synthesis of coumarin derivatives under solvent-free conditions

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

Abstract

Poly(4-vinylpyridine)-supported sulfuric acid is an efficient catalyst for the Pechmann condensation of acetoacetic esters with phenols, leading to the formation of coumarins in good yields within a few minutes under solvent-free microwave conditions. The catalyst used can be recovered and reused after activation.

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

Similar content being viewed by others

References

  1. Kennedy RO, Thornes RD (1997) Coumarins: biology, applications, and mode of action. Wiley, Chichester

    Google Scholar 

  2. Cravotto G, Nano GM, Palmisano G, Tagliapietra S (2001) Tetrahedron Asymmetry 12:707

  3. Wang CJ, Hsieh YJ, Chu CY, Lin YL, Tseng TH (2002) Cancer Lett 183:163

    Article  CAS  Google Scholar 

  4. Fan GJ, Mar W, Park MK, Wook Choi E, Kim K, Kim S (2001) Bioorg Med Chem Lett 11:2361

    Article  CAS  Google Scholar 

  5. Murray RDH, Mendez J, Brown SA (1982) The natural coumarins: occurrence, chemistry, and biochemistry. Wiley, New York

    Google Scholar 

  6. Zahradnik M (1992) The production and application of fluorescent brightening agents. Wiley, New York

    Google Scholar 

  7. Maeda M (1984) Laser dyes. Academic, New York

    Google Scholar 

  8. Sethna SM, Kong NP (1945) Chem Rev 36:1

    Article  CAS  Google Scholar 

  9. von Pechmann H, Duisberg C (1884) Ber Dtsch Chem Ges 17:929

    Article  Google Scholar 

  10. Johnson JR (1942) Org React 1:210

    Google Scholar 

  11. Jones G (1967) Org React 15:204

    CAS  Google Scholar 

  12. Shriner RL (1942) Org React 1:1

    Google Scholar 

  13. Yavari I, Shoar RH, Zonouzi A (1998) Tetrahedron Lett 39:2391

    Article  CAS  Google Scholar 

  14. Kumar V, Tomar S, Patel R, Yousaf A, Parmar VS, Malhotra SV (2008) Synth Commun 38:2646

    Article  CAS  Google Scholar 

  15. Chavan SP, Shivasankar K, Sivappa R, Kale R (2002) Tetrahedron Lett 43:8583

    Article  CAS  Google Scholar 

  16. Sethna SM, Shah NM, Shah RC (1938) J Chem Soc 228

  17. Valizadeh H, Shockravi A (2005) Tetrahedron Lett 46:3501

    Article  CAS  Google Scholar 

  18. Alexander VM, Bhat RP, Samant SD (2005) Tetrahedron Lett 46:6957

    Article  CAS  Google Scholar 

  19. Prajapati D, Gohain M (2007) Catal Lett 119:59

    Article  CAS  Google Scholar 

  20. Russel A, Frye JR (1941) Org Synth 21:22

    Google Scholar 

  21. Woods LL, Sapp J (1962) J Org Chem 27:3703

    Article  CAS  Google Scholar 

  22. Bulut M, Erk C (1996) Dyes Pigm 30:99

    Article  CAS  Google Scholar 

  23. Potdar MK, Mohile SS, Salunkhe MM (2001) Tetrahedron Lett 42:9285

    Article  CAS  Google Scholar 

  24. Khandekar AC, Khadikar BM (2002) Synlett 152

  25. Singh V, Singh J, Kaur KP, Kad GL (1997) J Chem Res (S) 58

  26. de la Hoz A, Moeno A, Vazquez E (1999) Synlett 608

  27. Frere S, Thiery V, Besson T (2001) Tetrahedron Lett 42:2791

    Article  CAS  Google Scholar 

  28. Hoefnagel AJ, Gunnewegh EA, Downing RS, van Bekkum H (1995) J Chem Soc Chem Commun 225

  29. Singh PR, Singh DU, Samant SD (2004) Synlett 1909

  30. Benaglia M, Puglisi A, Cozzi F (2003) Chem Rev 103:3401

    Article  CAS  Google Scholar 

  31. Rao V, Ashokan PV, Shridhar MH (2000) Mater Sci Eng A 276:266

    Article  Google Scholar 

  32. Borah KJ, Dutta P, Borah R (2011) Bull Korean Chem Soc 32:225

    Article  CAS  Google Scholar 

  33. Heravi MM, Khorasani M, Derikvand F, Oskooie HA, Bamoharram FF (2007) Catal Commun 8:1886

    Article  CAS  Google Scholar 

  34. Bahekar SS, Shinde DB (2004) Tetrahedron Lett 45:7999

    Article  CAS  Google Scholar 

  35. Rodrüíguez-Domínguez JC, Kirsch G (2006) Synthesis 1895

  36. Sun P, Hu Z (2005) Synth Commun 35:1875

    Article  CAS  Google Scholar 

  37. Kumar S, Saini A, Sandhu JS (2007) Arkivoc xv:18

  38. Hegedüs A, Hell Z (2006) Catal Lett 112:105

    Article  Google Scholar 

Download references

Acknowledgments

The authors are thankful to CSIR, New Delhi, India, for granting a Senior Research Fellowship to KKB.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ruli Borah.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Borah, K.J., Borah, R. Poly(4-vinylpyridine)-supported sulfuric acid: an efficient solid acid catalyst for the synthesis of coumarin derivatives under solvent-free conditions. Monatsh Chem 142, 1253–1257 (2011). https://doi.org/10.1007/s00706-011-0559-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-011-0559-6

Keywords

Navigation