Solvent-free multicomponent synthesis of 2-arylpyridines using p-sulfonic acid calix[6]arene as reusable catalyst

Autores
Sathicq, Angel Gabriel; Liberto, Natalia A.; Fernandes, Sergio A.; Romanelli, Gustavo Pablo
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
An new and efficient methodology for obtaining 2-arylpyrimidines based on the use of psulfonic acid calix[6]arene as organocatalyst is proposed. The methodology involves the formation of 1,2-dihydropyridine intermediates using a variety of aromatic aldehydes with methyl or ethyl acetoacetate and ammonium acetate, which are the same starting materials as in the Hantzsch reaction, under solvent-free reaction conditions, at 25 ºC, followed by air oxidation for 12 h. The catalyst efficiency is not compromised after its successive use in reactions. Eleven examples were obtained with very good to excellent yields of 2-arylpyridines (92%-62%). This is the first report about the use of calixarenes as catalyst in the multicomponent synthesis of 2-arylpyridines (molecules with biological activity potential)
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: Liberto, Natalia A.. Universidade Federal de Vicosa; Departamento de Quimica; Grupo de Quımica Supramolecular e Biomimetrica (GQSB); Brasil
Fil: Fernandes, Sergio A.. Universidade Federal de Vicosa; Departamento de Quimica; Grupo de Quımica Supramolecular e Biomimetrica (GQSB); Brasil
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
2-Arylpyridines
P-Sulfonic Acid Calix[6]Arene
Organocatalyts
Solvent-Free
Oxidant-Free Conditions
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:11336/6136
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Solvent-free multicomponent synthesis of 2-arylpyridines using p-sulfonic acid calix[6]arene as reusable catalystSathicq, Angel GabrielLiberto, Natalia A.Fernandes, Sergio A.Romanelli, Gustavo Pablo2-ArylpyridinesP-Sulfonic Acid Calix[6]AreneOrganocatalytsSolvent-FreeOxidant-Free Conditionshttps://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1An new and efficient methodology for obtaining 2-arylpyrimidines based on the use of psulfonic acid calix[6]arene as organocatalyst is proposed. The methodology involves the formation of 1,2-dihydropyridine intermediates using a variety of aromatic aldehydes with methyl or ethyl acetoacetate and ammonium acetate, which are the same starting materials as in the Hantzsch reaction, under solvent-free reaction conditions, at 25 ºC, followed by air oxidation for 12 h. The catalyst efficiency is not compromised after its successive use in reactions. Eleven examples were obtained with very good to excellent yields of 2-arylpyridines (92%-62%). This is the first report about the use of calixarenes as catalyst in the multicomponent synthesis of 2-arylpyridines (molecules with biological activity potential)Fil: Sathicq, Angel Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Centro de Investigación y Desarrollo En Ciencias Aplicadas; ArgentinaFil: Liberto, Natalia A.. Universidade Federal de Vicosa; Departamento de Quimica; Grupo de Quımica Supramolecular e Biomimetrica (GQSB); BrasilFil: Fernandes, Sergio A.. Universidade Federal de Vicosa; Departamento de Quimica; Grupo de Quımica Supramolecular e Biomimetrica (GQSB); BrasilFil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaElsevier Masson2015-03-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/6136Sathicq, Angel Gabriel; Liberto, Natalia A.; Fernandes, Sergio A.; Romanelli, Gustavo Pablo; Solvent-free multicomponent synthesis of 2-arylpyridines using p-sulfonic acid calix[6]arene as reusable catalyst; Elsevier Masson; Comptes Rendus Chimie; 18; 4; 10-3-2015; 374-3781631-0748enginfo:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/doi/10.1016/j.crci.2014.08.006info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1631074814002148info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:47:31Zoai:ri.conicet.gov.ar:11336/6136instacron: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 09:47:31.911CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Solvent-free multicomponent synthesis of 2-arylpyridines using p-sulfonic acid calix[6]arene as reusable catalyst
title Solvent-free multicomponent synthesis of 2-arylpyridines using p-sulfonic acid calix[6]arene as reusable catalyst
spellingShingle Solvent-free multicomponent synthesis of 2-arylpyridines using p-sulfonic acid calix[6]arene as reusable catalyst
Sathicq, Angel Gabriel
2-Arylpyridines
P-Sulfonic Acid Calix[6]Arene
Organocatalyts
Solvent-Free
Oxidant-Free Conditions
title_short Solvent-free multicomponent synthesis of 2-arylpyridines using p-sulfonic acid calix[6]arene as reusable catalyst
title_full Solvent-free multicomponent synthesis of 2-arylpyridines using p-sulfonic acid calix[6]arene as reusable catalyst
title_fullStr Solvent-free multicomponent synthesis of 2-arylpyridines using p-sulfonic acid calix[6]arene as reusable catalyst
title_full_unstemmed Solvent-free multicomponent synthesis of 2-arylpyridines using p-sulfonic acid calix[6]arene as reusable catalyst
title_sort Solvent-free multicomponent synthesis of 2-arylpyridines using p-sulfonic acid calix[6]arene as reusable catalyst
dc.creator.none.fl_str_mv Sathicq, Angel Gabriel
Liberto, Natalia A.
Fernandes, Sergio A.
Romanelli, Gustavo Pablo
author Sathicq, Angel Gabriel
author_facet Sathicq, Angel Gabriel
Liberto, Natalia A.
Fernandes, Sergio A.
Romanelli, Gustavo Pablo
author_role author
author2 Liberto, Natalia A.
Fernandes, Sergio A.
Romanelli, Gustavo Pablo
author2_role author
author
author
dc.subject.none.fl_str_mv 2-Arylpyridines
P-Sulfonic Acid Calix[6]Arene
Organocatalyts
Solvent-Free
Oxidant-Free Conditions
topic 2-Arylpyridines
P-Sulfonic Acid Calix[6]Arene
Organocatalyts
Solvent-Free
Oxidant-Free Conditions
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 An new and efficient methodology for obtaining 2-arylpyrimidines based on the use of psulfonic acid calix[6]arene as organocatalyst is proposed. The methodology involves the formation of 1,2-dihydropyridine intermediates using a variety of aromatic aldehydes with methyl or ethyl acetoacetate and ammonium acetate, which are the same starting materials as in the Hantzsch reaction, under solvent-free reaction conditions, at 25 ºC, followed by air oxidation for 12 h. The catalyst efficiency is not compromised after its successive use in reactions. Eleven examples were obtained with very good to excellent yields of 2-arylpyridines (92%-62%). This is the first report about the use of calixarenes as catalyst in the multicomponent synthesis of 2-arylpyridines (molecules with biological activity potential)
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: Liberto, Natalia A.. Universidade Federal de Vicosa; Departamento de Quimica; Grupo de Quımica Supramolecular e Biomimetrica (GQSB); Brasil
Fil: Fernandes, Sergio A.. Universidade Federal de Vicosa; Departamento de Quimica; Grupo de Quımica Supramolecular e Biomimetrica (GQSB); Brasil
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 An new and efficient methodology for obtaining 2-arylpyrimidines based on the use of psulfonic acid calix[6]arene as organocatalyst is proposed. The methodology involves the formation of 1,2-dihydropyridine intermediates using a variety of aromatic aldehydes with methyl or ethyl acetoacetate and ammonium acetate, which are the same starting materials as in the Hantzsch reaction, under solvent-free reaction conditions, at 25 ºC, followed by air oxidation for 12 h. The catalyst efficiency is not compromised after its successive use in reactions. Eleven examples were obtained with very good to excellent yields of 2-arylpyridines (92%-62%). This is the first report about the use of calixarenes as catalyst in the multicomponent synthesis of 2-arylpyridines (molecules with biological activity potential)
publishDate 2015
dc.date.none.fl_str_mv 2015-03-10
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/11336/6136
Sathicq, Angel Gabriel; Liberto, Natalia A.; Fernandes, Sergio A.; Romanelli, Gustavo Pablo; Solvent-free multicomponent synthesis of 2-arylpyridines using p-sulfonic acid calix[6]arene as reusable catalyst; Elsevier Masson; Comptes Rendus Chimie; 18; 4; 10-3-2015; 374-378
1631-0748
url http://hdl.handle.net/11336/6136
identifier_str_mv Sathicq, Angel Gabriel; Liberto, Natalia A.; Fernandes, Sergio A.; Romanelli, Gustavo Pablo; Solvent-free multicomponent synthesis of 2-arylpyridines using p-sulfonic acid calix[6]arene as reusable catalyst; Elsevier Masson; Comptes Rendus Chimie; 18; 4; 10-3-2015; 374-378
1631-0748
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.crci.2014.08.006
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1631074814002148
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
dc.publisher.none.fl_str_mv Elsevier Masson
publisher.none.fl_str_mv Elsevier Masson
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_ 1844613480804515840
score 13.070432

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