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Synthesis of mesoporous Ca-MCM catalysts and their use in suitable multicomponent synthesis of polyfunctionalized pyrans

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Abstract

Mesoporous Ca-MCM catalysts were prepared using a mixture of CaCO3, TEOS, cetyl trimethyl ammonium bromide (CTAB), triethanolamine (TEA), ethanol and H2O. Three catalysts with different CaCO3 contents, M-Ca 1 %, M-Ca 5 % and M-Ca 10 %, respectively, were prepared and characterized by N2 physisorption, XRD, FT-IR, XPS, TPD-CO2 and Pyridine-FTIR. A green and simple protocol was developed for the synthesis of 6-amino-4H-pyran scaffolds through a multicomponent coupling reaction of an aldehyde, malononitrile, and 1,3-dicarbonyl compound in different reaction solvents. This procedure was performed at room temperature (20 °C), obtaining good and excellent yields of 4H-pyran derivatives. The mesoporous materials are insoluble in polar media, which allows easy removal of the reaction products without affecting their catalytic activity. The leaching test showed an excellent stability, and Ca-MCM catalysts can be used three times without appreciable loss of their catalytic activity.

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Acknowledgments

This work was supported by CONICET (PIP 003), ANPCyT (PICT 0409) and La Plata University. Also, the authors thank Colciencias for financial support under the project 110965843004. Contract: Colciencias-UPTC 047-2015. GPR and AGS are CONICET members. J. J. Martínez thanks CONICET-OEA for a short fellowship in the UNLP.

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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

    Eliana Nope, Ángel G. Sathicq & Gustavo P. Romanelli

  2. Escuela de Ciencias Químicas, Facultad de Ciencias, Universidad Pedagógica y Tecnológica de Colombia UPTC, Avenida Central del Norte, Tunja, Boyacá, Colombia

    José J. Martínez & Hugo A. Rojas

  3. Cátedra de Química Orgánica, CISAV, Facultad de Ciencias Agrarias y Forestales, Universidad Nacional de La Plata, La Plata, Argentina

    Gustavo P. Romanelli

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  1. Eliana Nope
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  2. José J. Martínez
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  3. Hugo A. Rojas
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  4. Ángel G. Sathicq
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  5. Gustavo P. Romanelli
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Correspondence to José J. Martínez or Gustavo P. Romanelli.

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Nope, E., Martínez, J.J., Rojas, H.A. et al. Synthesis of mesoporous Ca-MCM catalysts and their use in suitable multicomponent synthesis of polyfunctionalized pyrans. Res Chem Intermed 43, 2103–2118 (2017). https://doi.org/10.1007/s11164-016-2749-7

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