On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from β-ketoesters

Autores
Martin, Anthony; Cheshmedzhieva, Diana; Palermo, Valeria; Liéby Muller, Frédéric; Romanelli, Gustavo Pablo; Gaudel Siri, Anouk; Coquerel, Yoann; Constantieux, Thierry; Rodriguez, Jean
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The regioselectivity of molecular sieves-promoted oxidative three-component reaction between -ketoesters, aromatic o-diamines and acrolein, leading to pyrido[1,2-a]benzimidazoles, has been investigated by a combination of experimental and theoretical studies. Molecular sieves act both as heterogeneous catalyst and dehydrating agent and their role has been modeled in the theoretical approach. The modulation of the reactivity of the aromatic diamine partner as a function of the nature of the substituents of the aromatic ring and its influence on the regioselectivity of the reaction could be rationalized.
Fil: Martin, Anthony. Centre National de la Recherche Scientifique; Francia
Fil: Cheshmedzhieva, Diana. University of Sofia; Bulgaria
Fil: Palermo, Valeria. 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: Liéby Muller, Frédéric. Centre National de la Recherche Scientifique; Francia
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
Fil: Gaudel Siri, Anouk. Centre National de la Recherche Scientifique; Francia
Fil: Coquerel, Yoann. Centre National de la Recherche Scientifique; Francia
Fil: Constantieux, Thierry. Centre National de la Recherche Scientifique; Francia
Fil: Rodriguez, Jean. Centre National de la Recherche Scientifique; Francia
Materia
MULTICOMPONENT REACTION
MICHAEL ADDITION
BENZIMIDAZOLE
MOLECULAR SIEVES
HETEROCYCLES
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/205052
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/205052
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from β-ketoestersMartin, AnthonyCheshmedzhieva, DianaPalermo, ValeriaLiéby Muller, FrédéricRomanelli, Gustavo PabloGaudel Siri, AnoukCoquerel, YoannConstantieux, ThierryRodriguez, JeanMULTICOMPONENT REACTIONMICHAEL ADDITIONBENZIMIDAZOLEMOLECULAR SIEVESHETEROCYCLEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The regioselectivity of molecular sieves-promoted oxidative three-component reaction between -ketoesters, aromatic o-diamines and acrolein, leading to pyrido[1,2-a]benzimidazoles, has been investigated by a combination of experimental and theoretical studies. Molecular sieves act both as heterogeneous catalyst and dehydrating agent and their role has been modeled in the theoretical approach. The modulation of the reactivity of the aromatic diamine partner as a function of the nature of the substituents of the aromatic ring and its influence on the regioselectivity of the reaction could be rationalized.Fil: Martin, Anthony. Centre National de la Recherche Scientifique; FranciaFil: Cheshmedzhieva, Diana. University of Sofia; BulgariaFil: Palermo, Valeria. 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: Liéby Muller, Frédéric. Centre National de la Recherche Scientifique; FranciaFil: 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; ArgentinaFil: Gaudel Siri, Anouk. Centre National de la Recherche Scientifique; FranciaFil: Coquerel, Yoann. Centre National de la Recherche Scientifique; FranciaFil: Constantieux, Thierry. Centre National de la Recherche Scientifique; FranciaFil: Rodriguez, Jean. Centre National de la Recherche Scientifique; FranciaElsevier France-Editions Scientifiques Medicales Elsevier2021-11-17info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/205052Martin, Anthony; Cheshmedzhieva, Diana; Palermo, Valeria; Liéby Muller, Frédéric; Romanelli, Gustavo Pablo; et al.; On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from β-ketoesters; Elsevier France-Editions Scientifiques Medicales Elsevier; Comptes Rendus Chimie; 25; 17-11-2021; 19-291631-0748CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.5802/crchim.137info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:18:33Zoai:ri.conicet.gov.ar:11336/205052instacron: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 10:18:33.314CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from β-ketoesters
title On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from β-ketoesters
spellingShingle On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from β-ketoesters
Martin, Anthony
MULTICOMPONENT REACTION
MICHAEL ADDITION
BENZIMIDAZOLE
MOLECULAR SIEVES
HETEROCYCLES
title_short On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from β-ketoesters
title_full On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from β-ketoesters
title_fullStr On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from β-ketoesters
title_full_unstemmed On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from β-ketoesters
title_sort On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from β-ketoesters
dc.creator.none.fl_str_mv Martin, Anthony
Cheshmedzhieva, Diana
Palermo, Valeria
Liéby Muller, Frédéric
Romanelli, Gustavo Pablo
Gaudel Siri, Anouk
Coquerel, Yoann
Constantieux, Thierry
Rodriguez, Jean
author Martin, Anthony
author_facet Martin, Anthony
Cheshmedzhieva, Diana
Palermo, Valeria
Liéby Muller, Frédéric
Romanelli, Gustavo Pablo
Gaudel Siri, Anouk
Coquerel, Yoann
Constantieux, Thierry
Rodriguez, Jean
author_role author
author2 Cheshmedzhieva, Diana
Palermo, Valeria
Liéby Muller, Frédéric
Romanelli, Gustavo Pablo
Gaudel Siri, Anouk
Coquerel, Yoann
Constantieux, Thierry
Rodriguez, Jean
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv MULTICOMPONENT REACTION
MICHAEL ADDITION
BENZIMIDAZOLE
MOLECULAR SIEVES
HETEROCYCLES
topic MULTICOMPONENT REACTION
MICHAEL ADDITION
BENZIMIDAZOLE
MOLECULAR SIEVES
HETEROCYCLES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The regioselectivity of molecular sieves-promoted oxidative three-component reaction between -ketoesters, aromatic o-diamines and acrolein, leading to pyrido[1,2-a]benzimidazoles, has been investigated by a combination of experimental and theoretical studies. Molecular sieves act both as heterogeneous catalyst and dehydrating agent and their role has been modeled in the theoretical approach. The modulation of the reactivity of the aromatic diamine partner as a function of the nature of the substituents of the aromatic ring and its influence on the regioselectivity of the reaction could be rationalized.
Fil: Martin, Anthony. Centre National de la Recherche Scientifique; Francia
Fil: Cheshmedzhieva, Diana. University of Sofia; Bulgaria
Fil: Palermo, Valeria. 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: Liéby Muller, Frédéric. Centre National de la Recherche Scientifique; Francia
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
Fil: Gaudel Siri, Anouk. Centre National de la Recherche Scientifique; Francia
Fil: Coquerel, Yoann. Centre National de la Recherche Scientifique; Francia
Fil: Constantieux, Thierry. Centre National de la Recherche Scientifique; Francia
Fil: Rodriguez, Jean. Centre National de la Recherche Scientifique; Francia
description The regioselectivity of molecular sieves-promoted oxidative three-component reaction between -ketoesters, aromatic o-diamines and acrolein, leading to pyrido[1,2-a]benzimidazoles, has been investigated by a combination of experimental and theoretical studies. Molecular sieves act both as heterogeneous catalyst and dehydrating agent and their role has been modeled in the theoretical approach. The modulation of the reactivity of the aromatic diamine partner as a function of the nature of the substituents of the aromatic ring and its influence on the regioselectivity of the reaction could be rationalized.
publishDate 2021
dc.date.none.fl_str_mv 2021-11-17
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/11336/205052
Martin, Anthony; Cheshmedzhieva, Diana; Palermo, Valeria; Liéby Muller, Frédéric; Romanelli, Gustavo Pablo; et al.; On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from β-ketoesters; Elsevier France-Editions Scientifiques Medicales Elsevier; Comptes Rendus Chimie; 25; 17-11-2021; 19-29
1631-0748
CONICET Digital
CONICET
url http://hdl.handle.net/11336/205052
identifier_str_mv Martin, Anthony; Cheshmedzhieva, Diana; Palermo, Valeria; Liéby Muller, Frédéric; Romanelli, Gustavo Pablo; et al.; On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from β-ketoesters; Elsevier France-Editions Scientifiques Medicales Elsevier; Comptes Rendus Chimie; 25; 17-11-2021; 19-29
1631-0748
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.5802/crchim.137
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier France-Editions Scientifiques Medicales Elsevier
publisher.none.fl_str_mv Elsevier France-Editions Scientifiques Medicales 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_ 1844614148697096192
score 13.070432

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