Skip to main content
Log in

Coumarins Preparation by Pechmann Reaction Under Ultrasound Irradiation. Synthesis of Hymecromone as Insecticide Intermediate

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Hymecromone, an important insecticide intermediate, were synthesized under solvent-free conditions by Pechmann reaction upon ultrasound irradiation in the presence of acid zeolites possessing different structural features. This methodology offers significant improvements for the synthesis of coumarins with regards to yield of product, simplicity in operation, and avoiding toxic catalysts and solvents.

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. O’Kennedy R, Thornes RD (1997) Coumarins: biology, applications and mode of action. John Wiley Sons, Chichester

    Google Scholar 

  2. Oyamada J, Jia C, Fuji-wara Y, Kitamura T (2002) Chem Lett 31:380

    Article  Google Scholar 

  3. Thapliyal P (1999) Ind J Chem 38B:726

    Google Scholar 

  4. Abate A, Dimartino V, Spina P, Costa PL, Lombardo C, Santini A, del Piano M, Alimonti P (2001) Drugs Exp Clin Res 27:223

    CAS  Google Scholar 

  5. Sing V (1997) J Chem Res 58

  6. Horning EC in: Organic Synthesis, Vol. III, Wiley, New York, 1955, 281

  7. Laufer MC, Hausmann H, Hölderich WF (2003) J Catal 218:315

    Article  CAS  Google Scholar 

  8. Reddy BM, Reddy VR, Giridar D (2001) Synth Commun 31:3603

    Article  CAS  Google Scholar 

  9. Gu Y, Zhang J, Duan Z, Deng Y (2005) Adv Synth Catal 347:512

    Article  CAS  Google Scholar 

  10. Selvakumar S, Chidambaram M, Singh AP (2007) Catal Commun 8:777

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  13. Reddy BM, Patil MK, Lakshmanan P (2006) J Mol Catal A Chem 256:290

    Article  CAS  Google Scholar 

  14. Romanelli GP, Bennardi D, Ruiz DM, Baronetti G Thomas HJ, Autino JC (2004) 45:8935

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

    Article  CAS  Google Scholar 

  16. Sabou R, Hoelderich WF, Ramprasad D, Weinand R (2005) J Catal 232:34

    Article  CAS  Google Scholar 

  17. Manhas MS, Ganguly SN, Mukherjee S, Jain AK, Bose AK (2006) Tetrahedron Lett 47:2423

    Article  CAS  Google Scholar 

  18. Čejka J, Wichterlová B (2002) Catal Rev 44:375

    Article  Google Scholar 

  19. Suslik KS (1990) Science 247:1439

    Article  Google Scholar 

  20. Suslik KS (ed) (1988) Ultrasound: its chemical, physical and biological effects. VCH, New York

    Google Scholar 

  21. Mason TJ (ed) (1990) Chemistry with ultrasound. Elsevier, London

  22. Adewuyi YG (2001) Ind Eng Chem Res 40:4681

    Article  CAS  Google Scholar 

  23. Chen MY, Lu KC, Lee ASY, Lin CC (2002) Tetrahedron Lett 43:2777

    Article  CAS  Google Scholar 

  24. Gholap AP, Venkatesan K, Daniel T, Lahoti RJ, Srinivasan KV (2003) Green Chem 6:693

    Article  CAS  Google Scholar 

  25. Lepore SD, He Y (2003) J Org Chem 68:8261

    Article  CAS  Google Scholar 

  26. Calvino-Casilda V, Martín-Aranda RM, López-Peinado AJ, Bejblová M, Čejka J (2008) Appl Catal A 338:130

    Article  CAS  Google Scholar 

  27. Deng S, Gangadharmath U, Chang CWT (2006) J Org Chem 71:5179

    Article  CAS  Google Scholar 

  28. Rubio-Gómez J, Martín-Aranda RM, Rojas-Cervantes ML, López-González J, de D Fierro JLG (1999) Carbon 37:213

    Article  Google Scholar 

  29. Martín-Aranda RM, Ortega-Cantero E, Rojas-Cervantes ML, Vicente-Rodríguez MA, Bañares-Muñoz MA (2002) Catal Lett 84:201

    Article  Google Scholar 

  30. López-Pestaña JM, Avila-Rey MJ, Martín-Aranda RM (2002) Green Chem 4:628

    Article  CAS  Google Scholar 

  31. Calvino-Casilda V, López-Peinado AJ, Martín-Aranda RM, Ferrera-Escudero S, Durán-Valle C (2004) Carbon 42:1363

    Article  CAS  Google Scholar 

  32. Calvino-Casilda V, Picallo M, Durán-Valle CJ, Fonseca I, López-Peinado AJ, Martín-Aranda RM (2005) Catal Today 107:237

    Google Scholar 

  33. Mason T (1991) Practical sonochemistry. Ellys Horwood, New York

    Google Scholar 

  34. Poliakoff M, Licence P (2007) Nature 450:810

    Article  CAS  Google Scholar 

  35. Bejblová M, Zones SI, Čejka J (2007) Appl Catal A 327:255

    Article  CAS  Google Scholar 

Download references

Acknowledgments

C.G.S. thanks the E.U. (Erasmus Mobility Program) Third Cycle Fellowship for the possibility to stay at the Charles University and Heyrovský Institute of Prague. V.C.C thanks the Universidad Nacional de Educación a Distancia (U.N.E.D.) for a PhD fellowship and the possibility to stay at J. Heyrovský Institute of Prague. Financial Support of this work by Spanish Ministerio de Educación y Ciencia (project MAT2007-66439-C02-01) is gratefully acknowledged. The work of J.Č. was financially supported by the Academy of Sciences of the Czech Republic (project 1QS400400560).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to R. M. Martín-Aranda or M. Bejblová.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gutiérrez-Sánchez, C., Calvino-Casilda, V., Pérez-Mayoral, E. et al. Coumarins Preparation by Pechmann Reaction Under Ultrasound Irradiation. Synthesis of Hymecromone as Insecticide Intermediate. Catal Lett 128, 318–322 (2009). https://doi.org/10.1007/s10562-008-9709-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-008-9709-9

Keywords

Navigation