Skip to main content
SpringerLink
Log in

Synergic Effects of Ionic Liquid and Microwave Irradiation in Promoting Trifluoromethylpyrazole Synthesis

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

The synthesis of 5-trifluoromethyl-1-phenyl-1H-pyrazoles from the reactions of 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones [CF3C(O)CH=C(R1)OR, where R = Me, Et; R1 = H, Me, Bu, i-Bu, Ph, 4-MeC6H4, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-IC6H4, fur-2-yl] with phenyl hydrazine in the presence of ionic liquid [BMIM][BF4] is reported. Synergic effects of ionic liquid and microwave irradiation in promoting pyrazole synthesis have been shown for the first time.

Graphical Abstract

R = Me, Et R1 = H, Me, Bu, i-Bu, Ph, 4-Me-C6H4, 4-F-C6H4, 4-Cl-C6H4, 4-Br-C6H4, 4-I-C6H4, Fur-2-yl.

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
Fig. 1

Similar content being viewed by others

References

  1. Wasserscheid P, Welton T (2008) Ionic liquids in synthesis, 2nd edn. WILEY-VCH, Weinheim, pp 57–165

    Google Scholar 

  2. Rogers RD, Seddon KR, Volkov S (2009) Green industrial applications of ionic liquids. Kluwer Academic Publishers, Dordrecht

    Google Scholar 

  3. Kuhnert N, Danks TN (2001) Green Chem 3:98

    Article  Google Scholar 

  4. Stadler A, Kappe AC (2001) Eur J Org Chem 5:919

    Article  Google Scholar 

  5. Polshettiwar V, Varma RS (2008) Acc Chem Res 41:629

    Article  CAS  Google Scholar 

  6. Martins MAP, Frizzo CP, Moreira DN, Buriol L, Machado P (2009) Chem Rev 109:4140

    Article  CAS  Google Scholar 

  7. Martinez-Palou R (2010) Mol Divers 14:3

    Article  CAS  Google Scholar 

  8. Martins MAP, Cunico W, Pereira CMP, Flores AFC, Bonacorso HG, Zanatta N (2004) Curr Org Synth 1:391

    Article  CAS  Google Scholar 

  9. Moreira DN, Longhi K, Frizzo CP, Bonacorso HG, Zanatta N, Martins MAP (2010) Catal Commun 11:476

    Article  CAS  Google Scholar 

  10. Frizzo CP, Moreira DN, Guarda EA, Fiss GF, Marzari MRB, Zanatta N, Bonacorso HG, Martins MAP (2009) Catal Commun 10:1153

    Article  CAS  Google Scholar 

  11. Martins MAP, Guarda EA, Frizzo CP, Moreira DN, Marzari MRB, Zanatta N, Bonacorso HG (2009) Catal Lett 130:93

    Article  CAS  Google Scholar 

  12. Buriol L, Frizzo CP, Marzari MRB, Moreira DN, Prola LDT, Zanatta N, Bonacorso HG, Martins MAP (2010) J Braz Chem Soc 21:1037

    Article  CAS  Google Scholar 

  13. Martins MAP, Beck PH, Machado P, Brondani S, Moura S, Zanatta N, Bonacorso HG, Flores AFC (2006) J Braz Chem Soc 17:411

    Google Scholar 

  14. Martins MAP, Pereira CMP, Cunico W, Moura S, Rosa FA, Peres RL, Machado P, Zanatta N, Bonacorso HG (2006) Ultrason Sonochem 13:364

    CAS  Google Scholar 

  15. Machado P, Lima GR, Rotta M, Bonacorso HG, Zanatta N, Martins MAP (2011) Ultrason Sonochem 18:293

    Article  CAS  Google Scholar 

  16. Martins MAP, Frizzo CP, Moreira DN, Bonacorso HG, Zanatta N (2008) Chem Rev 108:2015

    Article  CAS  Google Scholar 

  17. Penning TD, Talley JJ, Bertenshaw SR, Carter JS, Collins PW, Docter S, Graneto MJ, Lee LF, Malecha JW, Miyashiro JM, Rogers RS, Rogier DJ, Yu SS, Anderson GD, Burton EG, Cogburn JN, Gregory SA, Koboldt CM, Perkins WE, Seibert K, Veenhuizen AW, Zhang YY, Isakson PC (1997) J Med Chem 40:1347

    Article  CAS  Google Scholar 

  18. Terrett NK, Bell AS, Brown D, Ellis P (1996) Bioorg Med Chem Lett 6:1819

    Article  Google Scholar 

  19. Pavlik JW, Na Ayudhya TI, Tantayanon S (2003) J Heterocycl Chem 40:1087

    Article  CAS  Google Scholar 

  20. Habeeb AG, Rao PN, Knaus EE (2001) J Med Chem 44:3039

    Article  CAS  Google Scholar 

  21. Sloop JC, Lechner B, Waschington G, Bumgardner CL, Loehle WD, Creasy W (2008) Int J Chem Kinet 118:370

    Article  Google Scholar 

  22. Touzot A, Soufyaneb M, Berber H, Toupet L, Mirand C (2004) J Fluorine Chem 125:1299

    Article  CAS  Google Scholar 

  23. Souza R, Suarez PAZ, Consorti CS, Dupont J (2002) Org Synth 79:236

    Google Scholar 

  24. Flores AFC, Brondani S, Pizutti L, Martins MAP, Zanatta N, Bonacorso HG, Flores DC (2005) Synthesis 2744

  25. Bonacorso HG, Martins MAP, Bittencourt SRT, Lourega RV, Zanatta N, Flores AFC (1999) J Fluorine Chem 99:177

    Article  CAS  Google Scholar 

  26. Martins MAP, Moura S, Pereira CMP, Frizzo CP, Beck P, Zanatta N, Bonacorso HG, Flores AFC (2007) J Heterocycl Chem 44:1195

    Article  CAS  Google Scholar 

  27. Alkorta I, Alvarado M, Elguero J, García-Granda S, Goya P, Torre-Fernández L, Menéndez-Taboada L (2009) J Mol Struct 920:82

    Article  CAS  Google Scholar 

  28. Machado P, Campos PT, Rosa FA, Martins MAP (2007) Acta Crystallogr E63:04741

    Google Scholar 

  29. Farrugia LJ (1997) J Appl Crystallogr 30:565

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful to Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq Procs. No. 578426/2008-0; 471519/2009-0), Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul (FAPERGS/CNPq-PRONEX Edital No. 008/2009, Proc. No. 10/0037-8) and Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES/PROEX) for financial support. The fellowships from CNPq (M.A.P.M., L.B., D.N.M., M.R.B.M., L.D.T.P., N.Z., H.G.B.) and CAPES (C.P.F.) are also acknowledged.

Author information

Authors and Affiliations

  1. Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, RS, Brazil

    Lilian Buriol, Clarissa P. Frizzo, Liziê D. T. Prola, Dayse N. Moreira, Mara R. B. Marzari, Nilo Zanatta, Helio G. Bonacorso & Marcos A. P. Martins

  2. Laboratório de Química, Coordenação de Engenharia Ambiental, Universidade Federal do Tocantins, Av. NS 15 ALC NO 14, Bloco II, 109 Norte, Palmas, TO, Brazil

    Elisandra Scapin

Authors
  1. Lilian Buriol
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Clarissa P. Frizzo
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Liziê D. T. Prola
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Dayse N. Moreira
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Mara R. B. Marzari
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Elisandra Scapin
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Nilo Zanatta
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Helio G. Bonacorso
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Marcos A. P. Martins
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Clarissa P. Frizzo.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 53 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Buriol, L., Frizzo, C.P., Prola, L.D.T. et al. Synergic Effects of Ionic Liquid and Microwave Irradiation in Promoting Trifluoromethylpyrazole Synthesis. Catal Lett 141, 1130–1135 (2011). https://doi.org/10.1007/s10562-011-0571-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-011-0571-9

Keywords

Search

Navigation