One-pot synthesis of ferrocenyl-pyrimidones using a recyclable molibdosilicic H4SiMo12O40 heteropolyacid

A series of ferrocene-containing dihydropyrimidines (DHPs) were prepared by the one-pot Biginelli reaction of formylferrocene, 1,3-dicarbonyl component and urea/thiourea. The reaction was catalyzed by a commercial Keggin heteropolyacid (H4SiMo12O40) as a safe, clean and recyclable catalyst. Three di...

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Detalles Bibliográficos
Autores: Jios, Jorge Luis, Metzler Nolte, Nils, Vazquez, Patricia Graciela, Romanelli, Gustavo Pablo
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2016
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/39946
Acceso en línea:http://hdl.handle.net/11336/39946
Access Level:acceso abierto
Palabra clave:Ferrocene
Dihydropyrimidinones
Biginelli Reaction
Recyclable Keggin Heteropolyacid
One-Pot Reaction
https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
Descripción
Sumario:A series of ferrocene-containing dihydropyrimidines (DHPs) were prepared by the one-pot Biginelli reaction of formylferrocene, 1,3-dicarbonyl component and urea/thiourea. The reaction was catalyzed by a commercial Keggin heteropolyacid (H4SiMo12O40) as a safe, clean and recyclable catalyst. Three different synthetic protocols were examined in order to improve the yields of the reaction and to elucidate its mechanism. Intermediates of the competitive Knoevenagel reaction were also isolated. The methodology is operationally simple and provides access to highly substituted dihydropyrimidines containing ferrocene in very good yields. The catalyst can be used and recycled without appreciable loss of the catalytic activity.