Solvent-Free Synthesis of Functionalized Pyridine Derivatives Using Wells— -Dawson Heteropolyacid as Catalyst

Autores
Sanchez, Laura Mabel; Sathicq, Angel Gabriel; Jios, Jorge Luis; Baronetti, Graciela Teresita; Thomas, Horacio Jorge; Romanelli, Gustavo Pablo
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Wells-Dawson heteropolyacids (H6P2W18O62·24H2O) were used as catalysts in the Hantzsch-like multicomponent condensation reaction with 3-formylchromones as aldehyde component, a β-ketoester and ammonium acetate, under solvent-free conditions at 80 °C. Although the desired products were obtained, functionalized pyridines were the main reaction product and became the alternative route to dihydropyridine ring formation. Based on the proposed mechanisms for the formation of each of the obtained products, the multicomponent reaction was modified to afford only the functionalized pyridines (60–99%). Our procedure represents a clean alternative for the synthesis of several highly functionalized pyridines.
Fil: Sanchez, Laura Mabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Centro de Investigación y Desarrollo En Ciencias Aplicadas; Argentina
Fil: Sathicq, Angel Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Centro de Investigación y Desarrollo En Ciencias Aplicadas; Argentina
Fil: Jios, Jorge Luis. LASEISIC; Argentina
Fil: Baronetti, Graciela Teresita. Universidad de Buenos Aires. Facultad de Ingenieria. Departamento de Ingenieria Quimica. Laboratorio de Procesos Cataliticos; Argentina
Fil: Thomas, Horacio Jorge. Provincia de Buenos Aires. Gobernación. Comisión de Investigaciones Científicas. Planta Piloto Multiproposito; Argentina
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Centro de Investigación y Desarrollo En Ciencias Aplicadas; Argentina
Materia
Pyridine Derivatives
Benzopyran Derivatives
Multicomponent Reactions
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/4754
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/4754
network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Solvent-Free Synthesis of Functionalized Pyridine Derivatives Using Wells— -Dawson Heteropolyacid as CatalystSanchez, Laura MabelSathicq, Angel GabrielJios, Jorge LuisBaronetti, Graciela TeresitaThomas, Horacio JorgeRomanelli, Gustavo PabloPyridine DerivativesBenzopyran DerivativesMulticomponent Reactionshttps://purl.org/becyt/ford/2.5https://purl.org/becyt/ford/2Wells-Dawson heteropolyacids (H6P2W18O62·24H2O) were used as catalysts in the Hantzsch-like multicomponent condensation reaction with 3-formylchromones as aldehyde component, a β-ketoester and ammonium acetate, under solvent-free conditions at 80 °C. Although the desired products were obtained, functionalized pyridines were the main reaction product and became the alternative route to dihydropyridine ring formation. Based on the proposed mechanisms for the formation of each of the obtained products, the multicomponent reaction was modified to afford only the functionalized pyridines (60–99%). Our procedure represents a clean alternative for the synthesis of several highly functionalized pyridines.Fil: Sanchez, Laura Mabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Centro de Investigación y Desarrollo En Ciencias Aplicadas; ArgentinaFil: Sathicq, Angel Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Centro de Investigación y Desarrollo En Ciencias Aplicadas; ArgentinaFil: Jios, Jorge Luis. LASEISIC; ArgentinaFil: Baronetti, Graciela Teresita. Universidad de Buenos Aires. Facultad de Ingenieria. Departamento de Ingenieria Quimica. Laboratorio de Procesos Cataliticos; ArgentinaFil: Thomas, Horacio Jorge. Provincia de Buenos Aires. Gobernación. Comisión de Investigaciones Científicas. Planta Piloto Multiproposito; ArgentinaFil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Centro de Investigación y Desarrollo En Ciencias Aplicadas; ArgentinaElsevier2011-11-29info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/4754Sanchez, Laura Mabel; Sathicq, Angel Gabriel; Jios, Jorge Luis; Baronetti, Graciela Teresita; Thomas, Horacio Jorge; et al.; Solvent-Free Synthesis of Functionalized Pyridine Derivatives Using Wells— -Dawson Heteropolyacid as Catalyst; Elsevier; Tetrahedron Letters; 52; 34; 29-11-2011; 4412–44160040-4039enginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0040403911009889info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2011.06.048info:eu-repo/semantics/altIdentifier/issn/0040-4039info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:38:05Zoai:ri.conicet.gov.ar:11336/4754instacron: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:34982025-09-29 10:38:06.166CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Solvent-Free Synthesis of Functionalized Pyridine Derivatives Using Wells— -Dawson Heteropolyacid as Catalyst
title Solvent-Free Synthesis of Functionalized Pyridine Derivatives Using Wells— -Dawson Heteropolyacid as Catalyst
spellingShingle Solvent-Free Synthesis of Functionalized Pyridine Derivatives Using Wells— -Dawson Heteropolyacid as Catalyst
Sanchez, Laura Mabel
Pyridine Derivatives
Benzopyran Derivatives
Multicomponent Reactions
title_short Solvent-Free Synthesis of Functionalized Pyridine Derivatives Using Wells— -Dawson Heteropolyacid as Catalyst
title_full Solvent-Free Synthesis of Functionalized Pyridine Derivatives Using Wells— -Dawson Heteropolyacid as Catalyst
title_fullStr Solvent-Free Synthesis of Functionalized Pyridine Derivatives Using Wells— -Dawson Heteropolyacid as Catalyst
title_full_unstemmed Solvent-Free Synthesis of Functionalized Pyridine Derivatives Using Wells— -Dawson Heteropolyacid as Catalyst
title_sort Solvent-Free Synthesis of Functionalized Pyridine Derivatives Using Wells— -Dawson Heteropolyacid as Catalyst
dc.creator.none.fl_str_mv Sanchez, Laura Mabel
Sathicq, Angel Gabriel
Jios, Jorge Luis
Baronetti, Graciela Teresita
Thomas, Horacio Jorge
Romanelli, Gustavo Pablo
author Sanchez, Laura Mabel
author_facet Sanchez, Laura Mabel
Sathicq, Angel Gabriel
Jios, Jorge Luis
Baronetti, Graciela Teresita
Thomas, Horacio Jorge
Romanelli, Gustavo Pablo
author_role author
author2 Sathicq, Angel Gabriel
Jios, Jorge Luis
Baronetti, Graciela Teresita
Thomas, Horacio Jorge
Romanelli, Gustavo Pablo
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Pyridine Derivatives
Benzopyran Derivatives
Multicomponent Reactions
topic Pyridine Derivatives
Benzopyran Derivatives
Multicomponent Reactions
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.5
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv Wells-Dawson heteropolyacids (H6P2W18O62·24H2O) were used as catalysts in the Hantzsch-like multicomponent condensation reaction with 3-formylchromones as aldehyde component, a β-ketoester and ammonium acetate, under solvent-free conditions at 80 °C. Although the desired products were obtained, functionalized pyridines were the main reaction product and became the alternative route to dihydropyridine ring formation. Based on the proposed mechanisms for the formation of each of the obtained products, the multicomponent reaction was modified to afford only the functionalized pyridines (60–99%). Our procedure represents a clean alternative for the synthesis of several highly functionalized pyridines.
Fil: Sanchez, Laura Mabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Centro de Investigación y Desarrollo En Ciencias Aplicadas; Argentina
Fil: Sathicq, Angel Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Centro de Investigación y Desarrollo En Ciencias Aplicadas; Argentina
Fil: Jios, Jorge Luis. LASEISIC; Argentina
Fil: Baronetti, Graciela Teresita. Universidad de Buenos Aires. Facultad de Ingenieria. Departamento de Ingenieria Quimica. Laboratorio de Procesos Cataliticos; Argentina
Fil: Thomas, Horacio Jorge. Provincia de Buenos Aires. Gobernación. Comisión de Investigaciones Científicas. Planta Piloto Multiproposito; Argentina
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Centro de Investigación y Desarrollo En Ciencias Aplicadas; Argentina
description Wells-Dawson heteropolyacids (H6P2W18O62·24H2O) were used as catalysts in the Hantzsch-like multicomponent condensation reaction with 3-formylchromones as aldehyde component, a β-ketoester and ammonium acetate, under solvent-free conditions at 80 °C. Although the desired products were obtained, functionalized pyridines were the main reaction product and became the alternative route to dihydropyridine ring formation. Based on the proposed mechanisms for the formation of each of the obtained products, the multicomponent reaction was modified to afford only the functionalized pyridines (60–99%). Our procedure represents a clean alternative for the synthesis of several highly functionalized pyridines.
publishDate 2011
dc.date.none.fl_str_mv 2011-11-29
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/11336/4754
Sanchez, Laura Mabel; Sathicq, Angel Gabriel; Jios, Jorge Luis; Baronetti, Graciela Teresita; Thomas, Horacio Jorge; et al.; Solvent-Free Synthesis of Functionalized Pyridine Derivatives Using Wells— -Dawson Heteropolyacid as Catalyst; Elsevier; Tetrahedron Letters; 52; 34; 29-11-2011; 4412–4416
0040-4039
url http://hdl.handle.net/11336/4754
identifier_str_mv Sanchez, Laura Mabel; Sathicq, Angel Gabriel; Jios, Jorge Luis; Baronetti, Graciela Teresita; Thomas, Horacio Jorge; et al.; Solvent-Free Synthesis of Functionalized Pyridine Derivatives Using Wells— -Dawson Heteropolyacid as Catalyst; Elsevier; Tetrahedron Letters; 52; 34; 29-11-2011; 4412–4416
0040-4039
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0040403911009889
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2011.06.048
info:eu-repo/semantics/altIdentifier/issn/0040-4039
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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_ 1844614402888695808
score 13.070432

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