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New Vanadium Keggin Heteropolyacids Encapsulated in a Silica Framework: Recyclable Catalysts for the Synthesis of Highly Substituted Hexahydropyrimidines Under Suitable Conditions

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Abstract

Solid acid catalysts based on the direct incorporation of the vanadium Keggin heteropolyacid (PMo11V) structure during the synthesis of silica by the sol–gel technique, in acidic media using tetraethyl orthosilicate (PMo11VSiO21, PMo11VSiO22, PMo11VSiO23, and PMo11VSiO24), were prepared and characterized by 31P-NMR, FT-IR, XRD, and textural properties (SBET). The acidic characteristics of the catalysts were determined by potentiometric titration with n-butylamine. A series of highly substituted hexahydropyrimidines were synthesized using these new materials, encapsulated in a silica framework, as catalyst in solvent-free conditions. This methodology requires short reaction time (1.5 h), a temperature of 80 °C in solvent free-conditions to obtain good to excellent yields of trifluoromethyl-hexahydropyrimidine derivatives. The Keggin catalyst embedded in the silica matrix is insoluble in polar media, which allows easy removal of the reaction products without affecting their catalytic activity.

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Acknowledgments

The authors thank CONICET, ANPCyT, UNLP, Centre National de la Recherche Scientifique (CNRS) and the Université Paul Cézanne d’Aix-Marseille for their financial support. VP, AGS, PGV and GPR are members of CONICET.

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Authors and Affiliations

  1. Centro de Investigación y Desarrollo en Ciencias Aplicadas ‘Dr. Jorge J. Ronco’ (CINDECA-CCT-CONICET), Universidad Nacional de La Plata, Calle 47 No. 257, B1900AJK, La Plata, Argentina

    Valeria Palermo, Ángel Sathicq, Patricia Vázquez & Gustavo Romanelli

  2. Institut des Sciences Moléculaires de Marseille-UMR CNRS 7313 iSm2, Aix-Marseille Université Centre Saint Jérôme, Service 531, 13397, Marseille Cedex 20, France

    Thierry Constantieux & Jean Rodríguez

  3. Cátedra de Química Orgánica, Facultad de Ciencias Agrarias y Forestales, CISAV, Universidad Nacional de La Plata, Calles 60 y 119 s/n, B1904AAN, La Plata, Argentina

    Gustavo Romanelli

Authors
  1. Valeria Palermo
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  2. Ángel Sathicq
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  3. Thierry Constantieux
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  4. Jean Rodríguez
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  5. Patricia Vázquez
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  6. Gustavo Romanelli
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Correspondence to Gustavo Romanelli.

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Palermo, V., Sathicq, Á., Constantieux, T. et al. New Vanadium Keggin Heteropolyacids Encapsulated in a Silica Framework: Recyclable Catalysts for the Synthesis of Highly Substituted Hexahydropyrimidines Under Suitable Conditions. Catal Lett 145, 1022–1032 (2015). https://doi.org/10.1007/s10562-015-1498-3

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  • DOI: https://doi.org/10.1007/s10562-015-1498-3

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