An expedient route to heterocycles througha-arylation of ketones and arylamides bymicrowave induced thermal SRN1 reactions

Autores
Soria Castro, Silvia Mercedes; Caminos, Daniel Alberto; Peñeñory, Alicia Beatriz
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Microwave irradiation promotes a quick aromatic nucleophilic substitution by a thermally induced electrontransfer process to form new C–C bonds by the coupling of aryl radicals and enolate nucleophiles. Diverse2-aryl-1-phenylethanones can be prepared by the directa-arylation of acetophenone with differenthaloarenes. The ketone enolate anion is generated by deprotonation withtBuOK in DMSO and thereaction is carried out in a closed microwave vessel at 70–100 C for 10 min. This simple procedure alsoallows the synthesis of deoxybenzoin and indole heterocycle derivatives by inter- or intra-molecular ringclosure reactions, with moderate to excellent substitution yields.
Fil: Soria Castro, Silvia Mercedes. 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: Caminos, Daniel Alberto. 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: Peñeñory, Alicia Beatriz. 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
microwave
radical nucleophilic substitution
electron transfer
ketons
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:11336/31481
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling An expedient route to heterocycles througha-arylation of ketones and arylamides bymicrowave induced thermal SRN1 reactionsSoria Castro, Silvia MercedesCaminos, Daniel AlbertoPeñeñory, Alicia Beatrizmicrowaveradical nucleophilic substitutionelectron transferketonshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Microwave irradiation promotes a quick aromatic nucleophilic substitution by a thermally induced electrontransfer process to form new C–C bonds by the coupling of aryl radicals and enolate nucleophiles. Diverse2-aryl-1-phenylethanones can be prepared by the directa-arylation of acetophenone with differenthaloarenes. The ketone enolate anion is generated by deprotonation withtBuOK in DMSO and thereaction is carried out in a closed microwave vessel at 70–100 C for 10 min. This simple procedure alsoallows the synthesis of deoxybenzoin and indole heterocycle derivatives by inter- or intra-molecular ringclosure reactions, with moderate to excellent substitution yields.Fil: Soria Castro, Silvia Mercedes. 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: Caminos, Daniel Alberto. 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: Peñeñory, Alicia Beatriz. 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; ArgentinaRoyal Society of Chemistry2014-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/31481Peñeñory, Alicia Beatriz; Caminos, Daniel Alberto; Soria Castro, Silvia Mercedes; An expedient route to heterocycles througha-arylation of ketones and arylamides bymicrowave induced thermal SRN1 reactions; Royal Society of Chemistry; RSC Advances; 4; 3-2014; 17490-174972046-2069CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/c4ra00120finfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2014/RA/C4RA00120Finfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-05T10:43:00Zoai:ri.conicet.gov.ar:11336/31481instacron: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:34982025-11-05 10:43:00.361CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv An expedient route to heterocycles througha-arylation of ketones and arylamides bymicrowave induced thermal SRN1 reactions
title An expedient route to heterocycles througha-arylation of ketones and arylamides bymicrowave induced thermal SRN1 reactions
spellingShingle An expedient route to heterocycles througha-arylation of ketones and arylamides bymicrowave induced thermal SRN1 reactions
Soria Castro, Silvia Mercedes
microwave
radical nucleophilic substitution
electron transfer
ketons
title_short An expedient route to heterocycles througha-arylation of ketones and arylamides bymicrowave induced thermal SRN1 reactions
title_full An expedient route to heterocycles througha-arylation of ketones and arylamides bymicrowave induced thermal SRN1 reactions
title_fullStr An expedient route to heterocycles througha-arylation of ketones and arylamides bymicrowave induced thermal SRN1 reactions
title_full_unstemmed An expedient route to heterocycles througha-arylation of ketones and arylamides bymicrowave induced thermal SRN1 reactions
title_sort An expedient route to heterocycles througha-arylation of ketones and arylamides bymicrowave induced thermal SRN1 reactions
dc.creator.none.fl_str_mv Soria Castro, Silvia Mercedes
Caminos, Daniel Alberto
Peñeñory, Alicia Beatriz
author Soria Castro, Silvia Mercedes
author_facet Soria Castro, Silvia Mercedes
Caminos, Daniel Alberto
Peñeñory, Alicia Beatriz
author_role author
author2 Caminos, Daniel Alberto
Peñeñory, Alicia Beatriz
author2_role author
author
dc.subject.none.fl_str_mv microwave
radical nucleophilic substitution
electron transfer
ketons
topic microwave
radical nucleophilic substitution
electron transfer
ketons
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Microwave irradiation promotes a quick aromatic nucleophilic substitution by a thermally induced electrontransfer process to form new C–C bonds by the coupling of aryl radicals and enolate nucleophiles. Diverse2-aryl-1-phenylethanones can be prepared by the directa-arylation of acetophenone with differenthaloarenes. The ketone enolate anion is generated by deprotonation withtBuOK in DMSO and thereaction is carried out in a closed microwave vessel at 70–100 C for 10 min. This simple procedure alsoallows the synthesis of deoxybenzoin and indole heterocycle derivatives by inter- or intra-molecular ringclosure reactions, with moderate to excellent substitution yields.
Fil: Soria Castro, Silvia Mercedes. 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: Caminos, Daniel Alberto. 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: Peñeñory, Alicia Beatriz. 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 Microwave irradiation promotes a quick aromatic nucleophilic substitution by a thermally induced electrontransfer process to form new C–C bonds by the coupling of aryl radicals and enolate nucleophiles. Diverse2-aryl-1-phenylethanones can be prepared by the directa-arylation of acetophenone with differenthaloarenes. The ketone enolate anion is generated by deprotonation withtBuOK in DMSO and thereaction is carried out in a closed microwave vessel at 70–100 C for 10 min. This simple procedure alsoallows the synthesis of deoxybenzoin and indole heterocycle derivatives by inter- or intra-molecular ringclosure reactions, with moderate to excellent substitution yields.
publishDate 2014
dc.date.none.fl_str_mv 2014-03
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/11336/31481
Peñeñory, Alicia Beatriz; Caminos, Daniel Alberto; Soria Castro, Silvia Mercedes; An expedient route to heterocycles througha-arylation of ketones and arylamides bymicrowave induced thermal SRN1 reactions; Royal Society of Chemistry; RSC Advances; 4; 3-2014; 17490-17497
2046-2069
CONICET Digital
CONICET
url http://hdl.handle.net/11336/31481
identifier_str_mv Peñeñory, Alicia Beatriz; Caminos, Daniel Alberto; Soria Castro, Silvia Mercedes; An expedient route to heterocycles througha-arylation of ketones and arylamides bymicrowave induced thermal SRN1 reactions; Royal Society of Chemistry; RSC Advances; 4; 3-2014; 17490-17497
2046-2069
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/c4ra00120f
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2014/RA/C4RA00120F
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
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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 13.084122

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