Skip to main content
Log in

Synthesis of substituted coumarins catalyzed by sawdust-SO3H. An efficient and environmentally benign solid acid catalyst under solvent-free conditions

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

The sulfonated sawdust (SD-SO3H) was easily prepared by treatment of sawdust, a biomass waste material, with chlorosulfonic acid and characterized by elemental analysis, SEM and TGA. The bio-degradable solid acid catalyst has been applied to the Pechmann condensation reaction of phenols with β-ketoesters for the synthesis of coumarin derivatives under solvent-free conditions. This environmentally benign and inexpensive method has such advantages as simplicity in operation, high yields, low catalyst loading and short reaction time. The catalyst can be efficiently recycled with insignificant loss of activity.

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.

Similar content being viewed by others

References

  1. Lake, B.G., Food and Chemical Toxicology, 1999, vol. 37, p. 423.

    Article  CAS  Google Scholar 

  2. Weber, U.S., Steffen, B., and Siegers, C.P., Res. Commun. Mol. Pathol. Pharmacol., 1998, vol. 99, p. 193.

    CAS  Google Scholar 

  3. Zaha, A.A. and Hazem, A., The New Microbiologica, 2002, vol. 25, p. 213.

    CAS  Google Scholar 

  4. Maly, D.J., Leonetti, F., Backes, B.J., Dauber, D.S., Harris, J.L., Craik, C.S., and Ellman, J.A., J. Org. Chem., 2002, vol. 67, p. 910.

    Article  CAS  Google Scholar 

  5. Johnson, J.R., Org React., 1942, vol. 1, p. 210.

    Google Scholar 

  6. Jones, G., Org. React., 1967, vol. 15, p. 204.

    CAS  Google Scholar 

  7. Brufola, G., Fringuelli, F., Piermatti, O., and Pizzo, F., Heterocycles, 1996, vol. 43, p. 1257.

    Article  CAS  Google Scholar 

  8. Shriner, R.L., in Organic Reactions, John Wiley & Sons, Inc., 1942, vol. 1, 1.

    Google Scholar 

  9. Pechmann, H.v., Berichte der deutschen chemischen Gesellschaft, 1884, vol. 17, p. 929.

    Article  Google Scholar 

  10. Yavari, I., Hekmat-Shoar, R., and Zonouzi, A., Tetrahedron Lett., 1998, vol. 39, p. 2391.

    Article  CAS  Google Scholar 

  11. Patil, A.D., Freyer, A.J., Eggleston, D.S., Haltiwanger, R.C., Bean, M.F., Taylor, P.B., Caranfa, M.J., Breen, A.L., and Bartus, H.R., J. Med. Chem., 1993, vol. 36, p. 4131.

    Article  CAS  Google Scholar 

  12. Nadkarni, A.J. and Kudav, N.A., Indian J. Chem. B., 1981, vol. 20, p. 240.

    Google Scholar 

  13. Subhas Bose, D., Rudradas, A.P., and Hari Babu, M., Tetrahedron Lett., 2002, vol. 43, p. 9195.

    Article  CAS  Google Scholar 

  14. Sharma, G.V.M., Janardhan Reddy, J., Sree Lakshmi, P., and Radha Krishna, P., Tetrahedron Lett., 2005, vol. 46, p. 6119.

    Article  CAS  Google Scholar 

  15. Amoozadeh, A., Ahmadzadeh, M., and Kolvari, E., J. Chem., 2012, vol. 2013, p. 6.

    Google Scholar 

  16. Chaudhari, D.A.,Chem. Ind., 1983, p. 568.

  17. Khaligh, N.G., Ultrasonics Sonochemistry, 2013, vol. 20, p. 1062.

    Article  CAS  Google Scholar 

  18. Reddy, B.M., Thirupathi, B., and Patil, M.K., The Open Catalysis J., 2009, vol. 2, p. 33.

    Article  CAS  Google Scholar 

  19. Gunnewegh, E.A., Hoefnagel, A.J., and van Bekkum, H., J. Mol. Catal. A: Chemical, 1995, vol. 100, p. 87.

    Article  CAS  Google Scholar 

  20. Shirini, F. and Khaligh, N.G., Chin. J. Catal., 2013, vol. 34, p. 1890.

    Article  CAS  Google Scholar 

  21. Frère, S., Thiéry, V., and Besson, T., Tetrahedron Lett., 2001, vol. 42, p. 2791.

    Article  Google Scholar 

  22. Shirini, F., Zolfigol, M.A., and Albadi, J., JICS, 2010, vol. 7, p. 895.

    Article  CAS  Google Scholar 

  23. Shaterian, H.R. and Aghakhanizadeh, M., Chin J Catal., 2013, vol. 34, p. 1690.

    Article  CAS  Google Scholar 

  24. Naik, M.A., Mishra, B.G., and Dubey, A., Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2008, vol. 317, p. 234.

    Article  CAS  Google Scholar 

  25. Karami, B., Kiani, M., and Hoseini, M.A., Chin. J. Catal., 2014, vol. 35, p. 1206.

    Article  CAS  Google Scholar 

  26. Elhami, S. and Karami, S., Tech J Engin & App Sci., 2013, vol. 3, p. 828.

    Google Scholar 

  27. Tahanpesar, E., Elhami, S., and Mohammadi, M., Int. J. Sci. Res. in Environmental Sci., 2015, vol. 3, p. 38.

    Article  Google Scholar 

  28. Keri, R., Hosamani, K., and Seetharama Reddy, H., Catal Lett., 2009, vol. 131, p. 321.

    Article  CAS  Google Scholar 

  29. Prajapati, D. and Gohain, M., Catal Lett., 2007, vol. 119, p. 59.

    Article  CAS  Google Scholar 

  30. Kuarm, B.S., Crooks, P.A., and Rajitha, B., Int. J. Res. in Pharmaceutical and Biomedical Sci., 2012, vol. 3, p. 50.

    Google Scholar 

  31. Bahekar, S.S and Shinde, D.B., Tetrahedron Lett., 2004, vol. 45, p. 7999.

    Article  CAS  Google Scholar 

  32. Amoozadeh, A., Ahmadzadeh, M., and Kolvari, E., J. Chem., 2013, vol., 2013, p. 6.

    Article  Google Scholar 

  33. Dong, F., Jian, C., Kai, G., Qunrong, S., and Zuliang, L., Catal. Lett., 2008, vol. 121, p. 255.

    Article  Google Scholar 

  34. Singh, V., Singh, J., Preet Kaur, K., and Goverdhan, L.K., J. Chem. Res., Synopses, 1997, p. 58.

    Google Scholar 

  35. Kumar, P.S., Srinivasulu, N., Rajitha, B., Thirupathi Reddy, Y., Narsimha Reddy, P., and Udupi, R.H., Chem. Heterocycl. Compd., 2006, vol. 42, p. 172.

    Article  CAS  Google Scholar 

  36. Karami, B. and Kiani, M., Catal. Commun., 2011, vol. 14, p. 62.

    Article  CAS  Google Scholar 

  37. Sinhamahapatra, A., Sutradhar, N., Pahari, S., Bajaj, H.C., and Panda, A.B., Appl. Catal. A: General, 2011, vol. 394, p. 93.

    Article  CAS  Google Scholar 

  38. Reddy, B.M., Patil, M.K., and Lakshmanan, P., J. Mol. Catal. A: Chemical, 2006, vol. 256, p. 290.

    Article  CAS  Google Scholar 

  39. Zareyee, D. and Serehneh, M.J., J. Mol. Catal. A: Chemical, 2014, vol. 391, p. 88.

    Article  CAS  Google Scholar 

  40. Romanelli, G.P., Bennardi, D., Ruiz, D.M., Baronetti, G., Thomas, H.J., and Autino, J.C., Tetrahedron Lett., 2004, vol. 45, p. 8935.

    Article  CAS  Google Scholar 

  41. Hegedüs, A. and Hell, Z., Catal. Lett., 2006, vol. 112, p. 105.

    Article  Google Scholar 

  42. Maheswara, M., Siddaiah, V., Damu, G.L.V., Rao, Y.K., and Rao, C.V., J. Mol. Catal. A: Chemical, 2006, vol. 255, p. 49.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. Tahanpesar.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tahanpesar, E., Sarami, L. Synthesis of substituted coumarins catalyzed by sawdust-SO3H. An efficient and environmentally benign solid acid catalyst under solvent-free conditions. Russ J Gen Chem 85, 2135–2140 (2015). https://doi.org/10.1134/S1070363215090182

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363215090182

Keywords

Navigation