Selective and eco-friendly procedures for the synthesis of Benzimidazole derivatives. The role of Er(OTf)3 catalyst in the reaction selectivity

Autores
Herrera Cano, Natividad Carolina; Uranga, Jorge Gustavo; Nardi, Monica; Procopio, Antonio; Wunderlin, Daniel Alberto; Santiago, Ana Noemi
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
An improved and greener protocol for the synthesis of benzimidazole derivatives, starting from o-phenylenediamine, with differentaldehydes is reported. Double-condensation products were selectively obtained when Er(OTf)3 was used as the catalyst in the presenceof electron-rich aldehydes. Conversely, the formation of mono-condensation products was the preferred path in absence of thiscatalyst. One of the major advantages of these reactions was the formation of a single product, avoiding extensive isolation andpurification of products, which is frequently associated with these reactions.Theoretical calculations helped to understand the different reactivity established for these reactions. Thus, we found that the chargedensity on the oxygen of the carbonyl group has a significant impact on the reaction pathway. For instance, electron-rich aldehydesbetter coordinate to the catalyst, which favours the addition of the amine group to the carbonyl group, therefore facilitating the formationof double-condensation products.Reactions with aliphatic or aromatic aldehydes were possible, without using organic solvents and in a one-pot procedure with shortreaction time (2?5 min), affording single products in excellent yields (75?99%). This convenient and eco-friendly methodologyoffers numerous benefits with respect to other protocols reported for similar compounds.
Fil: Herrera Cano, Natividad Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Uranga, Jorge Gustavo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Nardi, Monica. Università della Calabria; Italia
Fil: Procopio, Antonio. Università Magna Graecia; Italia
Fil: Wunderlin, Daniel Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Ciencia y Tecnología de Alimentos Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Ciencia y Tecnología de Alimentos Córdoba; Argentina
Fil: Santiago, Ana Noemi. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Materia
ECO-FRIENDLY
SYNTHESIS
BENZIMIDAZOLE
ER(OTF)3
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:11336/47004
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Selective and eco-friendly procedures for the synthesis of Benzimidazole derivatives. The role of Er(OTf)3 catalyst in the reaction selectivityHerrera Cano, Natividad CarolinaUranga, Jorge GustavoNardi, MonicaProcopio, AntonioWunderlin, Daniel AlbertoSantiago, Ana NoemiECO-FRIENDLYSYNTHESISBENZIMIDAZOLEER(OTF)3https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1An improved and greener protocol for the synthesis of benzimidazole derivatives, starting from o-phenylenediamine, with differentaldehydes is reported. Double-condensation products were selectively obtained when Er(OTf)3 was used as the catalyst in the presenceof electron-rich aldehydes. Conversely, the formation of mono-condensation products was the preferred path in absence of thiscatalyst. One of the major advantages of these reactions was the formation of a single product, avoiding extensive isolation andpurification of products, which is frequently associated with these reactions.Theoretical calculations helped to understand the different reactivity established for these reactions. Thus, we found that the chargedensity on the oxygen of the carbonyl group has a significant impact on the reaction pathway. For instance, electron-rich aldehydesbetter coordinate to the catalyst, which favours the addition of the amine group to the carbonyl group, therefore facilitating the formationof double-condensation products.Reactions with aliphatic or aromatic aldehydes were possible, without using organic solvents and in a one-pot procedure with shortreaction time (2?5 min), affording single products in excellent yields (75?99%). This convenient and eco-friendly methodologyoffers numerous benefits with respect to other protocols reported for similar compounds.Fil: Herrera Cano, Natividad Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Uranga, Jorge Gustavo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Nardi, Monica. Università della Calabria; ItaliaFil: Procopio, Antonio. Università Magna Graecia; ItaliaFil: Wunderlin, Daniel Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Ciencia y Tecnología de Alimentos Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Ciencia y Tecnología de Alimentos Córdoba; ArgentinaFil: Santiago, Ana Noemi. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaBeilstein-Institut2016-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/47004Herrera Cano, Natividad Carolina; Uranga, Jorge Gustavo; Nardi, Monica; Procopio, Antonio; Wunderlin, Daniel Alberto; et al.; Selective and eco-friendly procedures for the synthesis of Benzimidazole derivatives. The role of Er(OTf)3 catalyst in the reaction selectivity; Beilstein-Institut; Beilstein Journal Of Organic Chemistry; 12; 11-2016; 2410-24191860-5397CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3762/bjoc.12.235info:eu-repo/semantics/altIdentifier/url/https://www.beilstein-journals.org/bjoc/articles/12/235info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:03:53Zoai:ri.conicet.gov.ar:11336/47004instacron: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:34982025-10-22 11:03:53.55CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Selective and eco-friendly procedures for the synthesis of Benzimidazole derivatives. The role of Er(OTf)3 catalyst in the reaction selectivity
title Selective and eco-friendly procedures for the synthesis of Benzimidazole derivatives. The role of Er(OTf)3 catalyst in the reaction selectivity
spellingShingle Selective and eco-friendly procedures for the synthesis of Benzimidazole derivatives. The role of Er(OTf)3 catalyst in the reaction selectivity
Herrera Cano, Natividad Carolina
ECO-FRIENDLY
SYNTHESIS
BENZIMIDAZOLE
ER(OTF)3
title_short Selective and eco-friendly procedures for the synthesis of Benzimidazole derivatives. The role of Er(OTf)3 catalyst in the reaction selectivity
title_full Selective and eco-friendly procedures for the synthesis of Benzimidazole derivatives. The role of Er(OTf)3 catalyst in the reaction selectivity
title_fullStr Selective and eco-friendly procedures for the synthesis of Benzimidazole derivatives. The role of Er(OTf)3 catalyst in the reaction selectivity
title_full_unstemmed Selective and eco-friendly procedures for the synthesis of Benzimidazole derivatives. The role of Er(OTf)3 catalyst in the reaction selectivity
title_sort Selective and eco-friendly procedures for the synthesis of Benzimidazole derivatives. The role of Er(OTf)3 catalyst in the reaction selectivity
dc.creator.none.fl_str_mv Herrera Cano, Natividad Carolina
Uranga, Jorge Gustavo
Nardi, Monica
Procopio, Antonio
Wunderlin, Daniel Alberto
Santiago, Ana Noemi
author Herrera Cano, Natividad Carolina
author_facet Herrera Cano, Natividad Carolina
Uranga, Jorge Gustavo
Nardi, Monica
Procopio, Antonio
Wunderlin, Daniel Alberto
Santiago, Ana Noemi
author_role author
author2 Uranga, Jorge Gustavo
Nardi, Monica
Procopio, Antonio
Wunderlin, Daniel Alberto
Santiago, Ana Noemi
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv ECO-FRIENDLY
SYNTHESIS
BENZIMIDAZOLE
ER(OTF)3
topic ECO-FRIENDLY
SYNTHESIS
BENZIMIDAZOLE
ER(OTF)3
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv An improved and greener protocol for the synthesis of benzimidazole derivatives, starting from o-phenylenediamine, with differentaldehydes is reported. Double-condensation products were selectively obtained when Er(OTf)3 was used as the catalyst in the presenceof electron-rich aldehydes. Conversely, the formation of mono-condensation products was the preferred path in absence of thiscatalyst. One of the major advantages of these reactions was the formation of a single product, avoiding extensive isolation andpurification of products, which is frequently associated with these reactions.Theoretical calculations helped to understand the different reactivity established for these reactions. Thus, we found that the chargedensity on the oxygen of the carbonyl group has a significant impact on the reaction pathway. For instance, electron-rich aldehydesbetter coordinate to the catalyst, which favours the addition of the amine group to the carbonyl group, therefore facilitating the formationof double-condensation products.Reactions with aliphatic or aromatic aldehydes were possible, without using organic solvents and in a one-pot procedure with shortreaction time (2?5 min), affording single products in excellent yields (75?99%). This convenient and eco-friendly methodologyoffers numerous benefits with respect to other protocols reported for similar compounds.
Fil: Herrera Cano, Natividad Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Uranga, Jorge Gustavo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Nardi, Monica. Università della Calabria; Italia
Fil: Procopio, Antonio. Università Magna Graecia; Italia
Fil: Wunderlin, Daniel Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Ciencia y Tecnología de Alimentos Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Ciencia y Tecnología de Alimentos Córdoba; Argentina
Fil: Santiago, Ana Noemi. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
description An improved and greener protocol for the synthesis of benzimidazole derivatives, starting from o-phenylenediamine, with differentaldehydes is reported. Double-condensation products were selectively obtained when Er(OTf)3 was used as the catalyst in the presenceof electron-rich aldehydes. Conversely, the formation of mono-condensation products was the preferred path in absence of thiscatalyst. One of the major advantages of these reactions was the formation of a single product, avoiding extensive isolation andpurification of products, which is frequently associated with these reactions.Theoretical calculations helped to understand the different reactivity established for these reactions. Thus, we found that the chargedensity on the oxygen of the carbonyl group has a significant impact on the reaction pathway. For instance, electron-rich aldehydesbetter coordinate to the catalyst, which favours the addition of the amine group to the carbonyl group, therefore facilitating the formationof double-condensation products.Reactions with aliphatic or aromatic aldehydes were possible, without using organic solvents and in a one-pot procedure with shortreaction time (2?5 min), affording single products in excellent yields (75?99%). This convenient and eco-friendly methodologyoffers numerous benefits with respect to other protocols reported for similar compounds.
publishDate 2016
dc.date.none.fl_str_mv 2016-11
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/11336/47004
Herrera Cano, Natividad Carolina; Uranga, Jorge Gustavo; Nardi, Monica; Procopio, Antonio; Wunderlin, Daniel Alberto; et al.; Selective and eco-friendly procedures for the synthesis of Benzimidazole derivatives. The role of Er(OTf)3 catalyst in the reaction selectivity; Beilstein-Institut; Beilstein Journal Of Organic Chemistry; 12; 11-2016; 2410-2419
1860-5397
CONICET Digital
CONICET
url http://hdl.handle.net/11336/47004
identifier_str_mv Herrera Cano, Natividad Carolina; Uranga, Jorge Gustavo; Nardi, Monica; Procopio, Antonio; Wunderlin, Daniel Alberto; et al.; Selective and eco-friendly procedures for the synthesis of Benzimidazole derivatives. The role of Er(OTf)3 catalyst in the reaction selectivity; Beilstein-Institut; Beilstein Journal Of Organic Chemistry; 12; 11-2016; 2410-2419
1860-5397
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3762/bjoc.12.235
info:eu-repo/semantics/altIdentifier/url/https://www.beilstein-journals.org/bjoc/articles/12/235
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
application/pdf
dc.publisher.none.fl_str_mv Beilstein-Institut
publisher.none.fl_str_mv Beilstein-Institut
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
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score 12.982451

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