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Evaluation of the synthesis of 1-(pentafluorophenyl)-4,5-dihydro-1H-pyrazoles using green metrics

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Abstract

1-(Pentafluorophenyl)-4,5-dihydro-1H-pyrazoles were synthesized from the cyclocondensation reactions of 4-alkoxy-1,1,1-trihalo-3-alken-2-ones (CX3C(O)CH=C(R1)OR, where X = F, Cl; R = Me, Et; R1 = H, Me, Et, n-Pr, i-Pr, n-Bu, i-Pent, Ph, 4-Cl-C6H4, 4-Br-C6H4, 4-F-C6H4) with pentafluorophenyl hydrazine. Pyrazoles were obtained under microwave irradiation in solvent-free conditions or under conventional heating in the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate, [BMIM][BF4]. These procedures furnished products in moderate to good yields in a short reaction time. Atom economy, reaction mass efficiency (RME), and environmental factor (E-factor) were determined for the cyclocondensation reaction performed under microwave (MW)/solvent-free and under conventional thermal heating/[BMIM][BF4] conditions. RME and E-factor indicated that the solvent-free procedure is invariably less green than [BMIM][BF4] when the isolated product was considered.

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Acknowledgments

The authors thank the Conselho Nacional de Desenvolvimento Científico e Tecnológico—CNPq (Universal/Proc. 485893/2007-0; Universal/Proc. 471519/2009-0; MAPA/Proc. 578426/2008-0) and the Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul—FAPERGS (PRONEX/Proc. 10/0037-8; ARD/Proc. 11/1777-6) for the financial support. The fellowships from CNPq (M.A.P.M., N.Z., H.G.B., D.N.M., M.R.B.M., M.Z.), CAPES (L.B., C.P.F.), and FAPERGS are also acknowledged.

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Authors and Affiliations

  1. Núcleo de Química de Heterociclos (NUQUIMHE), Departament of Chemistry, Federal University of Santa Maria, Santa Maria, RS, 97105-900, Brazil

    Marcos A. P. Martins, Paulo H. Beck, Lilian Buriol, Clarissa P. Frizzo, Dayse N. Moreira, Mara R. B. Marzari, Marcileia Zanatta, Pablo Machado, Nilo Zanatta & Helio G. Bonacorso

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  1. Marcos A. P. Martins
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  2. Paulo H. Beck
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  3. Lilian Buriol
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  4. Clarissa P. Frizzo
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  5. Dayse N. Moreira
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  6. Mara R. B. Marzari
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  7. Marcileia Zanatta
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  8. Pablo Machado
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  9. Nilo Zanatta
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  10. Helio G. Bonacorso
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Corresponding author

Correspondence to Clarissa P. Frizzo.

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Martins, M.A.P., Beck, P.H., Buriol, L. et al. Evaluation of the synthesis of 1-(pentafluorophenyl)-4,5-dihydro-1H-pyrazoles using green metrics. Monatsh Chem 144, 1043–1050 (2013). https://doi.org/10.1007/s00706-013-0930-x

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  • DOI: https://doi.org/10.1007/s00706-013-0930-x

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