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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/47004
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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 Técnicas2025-09-29T09:35:48Zoai: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:34982025-09-29 09:35:49.198CONICET 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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1844613118328569856 |
score |
13.070432 |