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An E-factor minimized solvent-free protocol for the preparation of 4,5-dihydro-5-(trifluoromethyl)-1H-pyrazoles

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Abstract

The efficient synthesis of 4,5-dihydro-1H-pyrazoles from the reaction of 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones [CF3C(O)CH=C(R1)(OR), where R = Me, Et and R1 = H, Me, Et, Pr, i-Bu, Ph, 4-Me-C6H4, 4-F-C6H4, 4-Cl-C6H4, fur-2-yl, Naphth-2-yl, biphenyl-4-yl] and ethyl 3-hydrazino-3-oxopropionate [NH2NHC(O)CH2C(O)OEt] is reported. The products were obtained in good yields (72–87%). Two protocols were developed: (1) conventional thermal heating using EtOH as solvent and under solvent-free conditions, and (2) a microwave-assisted method using EtOH as solvent and under solvent-free conditions. The E-factor was determined for all protocols, and the results showed that the microwave-assisted method under solvent-free conditions results in a greener process.

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Acknowledgments

The authors are grateful to Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq procs. nos. 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., M.R.B.M., L.D.T.P., T.S.M., N.Z., H.G.B.) and CAPES (D.N.M., C.P.F.) are also acknowledged.

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Authors and Affiliations

  1. Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, RS, 97105-900, Brazil

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

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  1. Lilian Buriol
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  2. Clarissa P. Frizzo
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  3. Dayse N. Moreira
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  4. Liziê D. T. Prola
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  5. Mara R. B. Marzari
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  6. Taiana S. München
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  7. Nilo Zantta
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  8. Helio G. Bonacorso
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  9. Marcos A. P. Martins
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Correspondence to Marcos A. P. Martins.

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Buriol, L., Frizzo, C.P., Moreira, D.N. et al. An E-factor minimized solvent-free protocol for the preparation of 4,5-dihydro-5-(trifluoromethyl)-1H-pyrazoles. Monatsh Chem 142, 515–520 (2011). https://doi.org/10.1007/s00706-011-0464-z

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  • DOI: https://doi.org/10.1007/s00706-011-0464-z

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