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

Autores
Jios, Jorge Luis; Metzler Nolte, Nils; Vazquez, Patricia Graciela; Romanelli, Gustavo Pablo
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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.
Fil: Jios, Jorge Luis. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina
Fil: Metzler Nolte, Nils. Ruhr Universität Bochum; Alemania
Fil: Vazquez, Patricia Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Materia
Ferrocene
Dihydropyrimidinones
Biginelli Reaction
Recyclable Keggin Heteropolyacid
One-Pot Reaction
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/39946
Acceder
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network_name_str CONICET Digital (CONICET)
spelling One-pot synthesis of ferrocenyl-pyrimidones using a recyclable molibdosilicic H4SiMo12O40 heteropolyacidJios, Jorge LuisMetzler Nolte, NilsVazquez, Patricia GracielaRomanelli, Gustavo PabloFerroceneDihydropyrimidinonesBiginelli ReactionRecyclable Keggin HeteropolyacidOne-Pot Reactionhttps://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A 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.Fil: Jios, Jorge Luis. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; ArgentinaFil: Metzler Nolte, Nils. Ruhr Universität Bochum; AlemaniaFil: Vazquez, Patricia Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaSpringer2016-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/39946Jios, Jorge Luis; Metzler Nolte, Nils; Vazquez, Patricia Graciela; Romanelli, Gustavo Pablo; One-pot synthesis of ferrocenyl-pyrimidones using a recyclable molibdosilicic H4SiMo12O40 heteropolyacid; Springer; Research on Chemical Intermediates; 42; 2; 2-2016; 977-9860922-6168CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1007/s11164-015-2067-5info:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007%2Fs11164-015-2067-5info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:20:36Zoai:ri.conicet.gov.ar:11336/39946instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-15 14:20:36.587CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv One-pot synthesis of ferrocenyl-pyrimidones using a recyclable molibdosilicic H4SiMo12O40 heteropolyacid
title One-pot synthesis of ferrocenyl-pyrimidones using a recyclable molibdosilicic H4SiMo12O40 heteropolyacid
spellingShingle One-pot synthesis of ferrocenyl-pyrimidones using a recyclable molibdosilicic H4SiMo12O40 heteropolyacid
Jios, Jorge Luis
Ferrocene
Dihydropyrimidinones
Biginelli Reaction
Recyclable Keggin Heteropolyacid
One-Pot Reaction
title_short One-pot synthesis of ferrocenyl-pyrimidones using a recyclable molibdosilicic H4SiMo12O40 heteropolyacid
title_full One-pot synthesis of ferrocenyl-pyrimidones using a recyclable molibdosilicic H4SiMo12O40 heteropolyacid
title_fullStr One-pot synthesis of ferrocenyl-pyrimidones using a recyclable molibdosilicic H4SiMo12O40 heteropolyacid
title_full_unstemmed One-pot synthesis of ferrocenyl-pyrimidones using a recyclable molibdosilicic H4SiMo12O40 heteropolyacid
title_sort One-pot synthesis of ferrocenyl-pyrimidones using a recyclable molibdosilicic H4SiMo12O40 heteropolyacid
dc.creator.none.fl_str_mv Jios, Jorge Luis
Metzler Nolte, Nils
Vazquez, Patricia Graciela
Romanelli, Gustavo Pablo
author Jios, Jorge Luis
author_facet Jios, Jorge Luis
Metzler Nolte, Nils
Vazquez, Patricia Graciela
Romanelli, Gustavo Pablo
author_role author
author2 Metzler Nolte, Nils
Vazquez, Patricia Graciela
Romanelli, Gustavo Pablo
author2_role author
author
author
dc.subject.none.fl_str_mv Ferrocene
Dihydropyrimidinones
Biginelli Reaction
Recyclable Keggin Heteropolyacid
One-Pot Reaction
topic Ferrocene
Dihydropyrimidinones
Biginelli Reaction
Recyclable Keggin Heteropolyacid
One-Pot Reaction
purl_subject.fl_str_mv 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
dc.description.none.fl_txt_mv 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.
Fil: Jios, Jorge Luis. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina
Fil: Metzler Nolte, Nils. Ruhr Universität Bochum; Alemania
Fil: Vazquez, Patricia Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
description 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.
publishDate 2016
dc.date.none.fl_str_mv 2016-02
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/39946
Jios, Jorge Luis; Metzler Nolte, Nils; Vazquez, Patricia Graciela; Romanelli, Gustavo Pablo; One-pot synthesis of ferrocenyl-pyrimidones using a recyclable molibdosilicic H4SiMo12O40 heteropolyacid; Springer; Research on Chemical Intermediates; 42; 2; 2-2016; 977-986
0922-6168
CONICET Digital
CONICET
url http://hdl.handle.net/11336/39946
identifier_str_mv Jios, Jorge Luis; Metzler Nolte, Nils; Vazquez, Patricia Graciela; Romanelli, Gustavo Pablo; One-pot synthesis of ferrocenyl-pyrimidones using a recyclable molibdosilicic H4SiMo12O40 heteropolyacid; Springer; Research on Chemical Intermediates; 42; 2; 2-2016; 977-986
0922-6168
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1007/s11164-015-2067-5
info:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007%2Fs11164-015-2067-5
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Springer
publisher.none.fl_str_mv Springer
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1846082583523229696
score 13.22299

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