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An efficient synthesis of 1-cyanoacetyl-5-halomethyl-4,5-dihydro-1H-pyrazoles in ionic liquid

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Abstract

The synthesis of eleven 1-cyanoacetyl-5-hydroxy-5-halomethyl-4,5-dihydro-1H-pyrazoles from the reaction of 4-alkoxy-3-alken-2-ones f(R 3C(O)C(R 2) = C(R 1)OR, where R 3 = CF3, CCl3, CHCl2, CO2 Et; R 2/R 1 = H/H, H/Me, H/Et, -(CH2)4-, Me/H, H/Pr, and R = Me, Et) with cyanoacetohydrazide is reported. The reaction was carried out in the ionic liquid ([bmim][BF4]) and molecular solvents. The results showed that when the ionic liquid was used as reaction medium, the reaction time was drastically decreased and the yield was improved.

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Authors and Affiliations

  1. Núcleo de Química de Heterociclos – NUQUIMHE, Universidade Federal de Santa Maria, Santa Maria, RS, Brazil

    Dayse N. Moreira, Clarissa P. Frizzo, Kelvis Longhi, Nilo Zanatta, Helio G. Bonacorso & Marcos A. P. Martins

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  1. Dayse N. Moreira
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  2. Clarissa P. Frizzo
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  3. Kelvis Longhi
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  4. Nilo Zanatta
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  5. Helio G. Bonacorso
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  6. Marcos A. P. Martins
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Corresponding author

Correspondence to Marcos A. P. Martins.

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Correspondence: Marcos A. P. Martins, Núcleo de Química de Heterociclos – NUQUIMHE, Universidade Federal de Santa Maria, Santa Maria, RS, Brazil.

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Moreira, D., Frizzo, C., Longhi, K. et al. An efficient synthesis of 1-cyanoacetyl-5-halomethyl-4,5-dihydro-1H-pyrazoles in ionic liquid. Monatsh Chem 139, 1049–1054 (2008). https://doi.org/10.1007/s00706-008-0874-8

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