Imidazolium supported iron-chloroglycine complex, a good turnover recyclable catalyst for the solvent free synthesis of 3, 4-dihydropyrimidin-2(1H)-ones – promoted by ultrasound irradiation

Priya Ramasamy Shunmuga, Uma maheswari Govindhasamay, Deepa Manicam, Karthikeyan Parasuraman

Abstract


Abstract. A novel large band gap 1-glycyl-3-methyl imidazolium chloride-iron (III) complex [[Gmim]Cl-Fe(III)] was found to be a heterogeneous catalyst for an efficient and solvent free synthesis of 3,4-dihydropyrimidin-2(1H)-ones by condensation of substituted aldehydes, ethyl acetoacetate and urea (or) thiourea with tremendous yields in high turnover number (4.1X102 to 18.8X102)  at ambient temperature using ultrasound irradiation as the activation mode of reaction. This operation formulates very interesting, ecological perspective due to simple reaction condition, isolation and purification of products. In addition, this methodology offers a competitive recyclability of the catalyst without a significant loss of its catalytic activity and could be readily reused, thus making this protocol more environmentally acceptable whilst no catalyst leaching was observed.

 

Resumen. Se descubrió que un complejo novedoso de banda ancha 1-glicil-3-metilimidazolio cloruro de hierro (III) [[Gmim] Cl-Fe (III)] es un catalizador heterogéneo para una síntesis eficiente y libre de solventes de 3,4- dihidropirimidin-2 (1H) -ones por condensación de aldehídos sustituidos, acetoacetato de etilo y tiourea urea (o) con tremendos rendimientos en alto número de recambio (4.1X102 a 18.8X102) a temperatura ambiente mediante irradiación con ultrasonido como modo de activación de reacción. Esta operación formula una perspectiva ecológica muy interesante debido a la condición de reacción simple, el aislamiento y la purificación de los productos. Además, esta metodología ofrece una reciclabilidad competitiva del catalizador sin una pérdida significativa de su actividad catalítica y podría reutilizarse fácilmente, lo que hace que este protocolo sea más aceptable para el medio ambiente sin que se observe lixiviación del catalizador.

 


Keywords


Iron(III) complex; Multi-component reactions; Ultrasonication; Ionic liquid; Green aproach

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DOI: http://dx.doi.org/10.29356/jmcs.v62i3.779

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Journal of the Mexican Chemical Society (J. Mex. Chem. Soc.) Vol 62, No 2 (2018). Quarterly publication (April-June). Edited and distributed by Sociedad Química de México, A.C. Barranca del Muerto 26, Col. Crédito Constructor, Del. Benito Juárez, C.P. 03940, Mexico City. Phone: +5255 56626837; +5255 56626823 Contact: soquimex@sqm.org.mx http://www.sqm.org.mx Editor-in-Chief: Ignacio González-Martínez. Indexed Journal. Certificate of reserved rights for recurrent publications under digital distribution granted by the Instituto Nacional del Derecho de Autor (INDAUTOR): 04-2018-091118040000-203. Certificate of lawful title and content: Under procedure. ISSN-e granted by the Instituto Nacional del Derecho de Autor (INDAUTOR): 2594-0317. ISSN granted by the Instituto Nacional del Derecho de Autor (INDAUTOR): 1870-249X. Postal registration of printed matter deposited by editors or agents granted by SEPOMEX: IM09-0312 Copyright © Sociedad Química de México, A.C. Total or partial reproduction is prohibited without written permission of the right holder. The Figures/schemes quality and the general contents of this publication are full responsibility of the authors. Updated December 12th, 2018 by Adriana Vázquez (editorial assistant, e-mail: editor.jmcs@gmail.com), J. Mex. Chem. Soc., Sociedad Química de México, A.C.