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Ionic liquid and Lewis acid combination in the synthesis of novel (E)-1-(benzylideneamino)-3-cyano-6-(trifluoromethyl)-1H-2-pyridones

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Abstract

In this work, a new catalytic system to synthesize a series of new (E)-1-(benzylideneamino)-3-cyano-6-(trifluoromethyl)-1H-2-pyridones from the cyclocondensation reaction of benzylidene cyanoacetohydrazide with 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones [CF3C(O)C(R2) = C(R1)(OR), where R = Me, Et; R1 = H, Me, Pr, Bu, Ph, 4-Me-Ph, 4-F-Ph, 4-Cl-Ph, 4-Br-Ph; R2 = H, Me and R1,R2 = –(CH2)4–] is presented. The products were obtained at room temperature in moderate to good yields (42–87%). Comparison of the catalytic system with a conventional method was not possible, because the products were obtained only when the new catalyst system—consisting of triethylamine and Lewis acid in ionic liquid [BMIM][BF4]—was used.

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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) for financial support. The fellowships from CNPq (M.A.P.M., N.Z., H.G.B., P.T.C., M.R.B.M., D.N.M., K.L.), CAPES (C.P.F., PRODOC/Proc. 2684-32/2010, and L.B.), and FAPERGS are also acknowledged. The authors also thank Maria Ángeles García and Rosa M. Claramunt (UNED, Madrid, Spain) for the 13C CPMAS-NMR analysis.

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Authors and Affiliations

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

    Dayse N. Moreira, Clarissa P. Frizzo, Kelvis Longhi, Aline B. Soares, Mara R. B. Marzari, Lilian Buriol, Sergio Brondani, 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. Aline B. Soares
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  5. Mara R. B. Marzari
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  6. Lilian Buriol
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  7. Sergio Brondani
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  9. Helio G. Bonacorso
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  10. Marcos A. P. Martins
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Corresponding author

Correspondence to Clarissa P. Frizzo.

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Moreira, D.N., Frizzo, C.P., Longhi, K. et al. Ionic liquid and Lewis acid combination in the synthesis of novel (E)-1-(benzylideneamino)-3-cyano-6-(trifluoromethyl)-1H-2-pyridones. Monatsh Chem 142, 1265–1270 (2011). https://doi.org/10.1007/s00706-011-0563-x

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