Synthesis of Benzo-Fused Heterocycles by Intramolecular alpha-Arylation of Ketone Enolate Anions

Autores
Guastavino, Javier Fernando; Rossi, Roberto Arturo
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A two-step synthesis of six-, seven-, eight-, and nine-member benzo-fused heterocycles in good to excellent yields is reported. The synthetic strategy involves the generation of a new intramolecular alpha-aryl ketone bond by the photostimulated SRN1 reaction of ketone enolate anions linked to a pendant haloarene as the key step. On the other hand, an intramolecular CAr-CAr coupling led to the formation of five- and six-member benzo-fused heterocycles (9H-carbazole and phenanthridine) when an aromatic amide anion is competitively formed
Fil: Guastavino, Javier Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química (i); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto de Investigaciones en Físicoquímica de Córdoba; Argentina. Universidad Nacional de Córdoba; Argentina
Fil: Rossi, Roberto Arturo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto de Investigaciones en Físicoquímica de Córdoba; Argentina. Universidad Nacional de Córdoba; Argentina
Materia
Benzo-Fused Heterocycles
Srn1 Reactions
Ketone Enolate Anions
Arylation
Alpha-Aryl Ketone
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:11336/10963
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/10963
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of Benzo-Fused Heterocycles by Intramolecular alpha-Arylation of Ketone Enolate AnionsGuastavino, Javier FernandoRossi, Roberto ArturoBenzo-Fused HeterocyclesSrn1 ReactionsKetone Enolate AnionsArylationAlpha-Aryl Ketonehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A two-step synthesis of six-, seven-, eight-, and nine-member benzo-fused heterocycles in good to excellent yields is reported. The synthetic strategy involves the generation of a new intramolecular alpha-aryl ketone bond by the photostimulated SRN1 reaction of ketone enolate anions linked to a pendant haloarene as the key step. On the other hand, an intramolecular CAr-CAr coupling led to the formation of five- and six-member benzo-fused heterocycles (9H-carbazole and phenanthridine) when an aromatic amide anion is competitively formedFil: Guastavino, Javier Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química (i); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto de Investigaciones en Físicoquímica de Córdoba; Argentina. Universidad Nacional de Córdoba; ArgentinaFil: Rossi, Roberto Arturo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto de Investigaciones en Físicoquímica de Córdoba; Argentina. Universidad Nacional de Córdoba; ArgentinaAmerican Chemical Society2012-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/10963Guastavino, Javier Fernando; Rossi, Roberto Arturo; Synthesis of Benzo-Fused Heterocycles by Intramolecular alpha-Arylation of Ketone Enolate Anions; American Chemical Society; Journal Of Organic Chemistry; 77; 1; 1-2012; 460-4720022-3263enginfo:eu-repo/semantics/altIdentifier/doi/10.1021/jo202012ninfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/jo202012ninfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:32:59Zoai:ri.conicet.gov.ar:11336/10963instacron: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 09:32:59.963CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of Benzo-Fused Heterocycles by Intramolecular alpha-Arylation of Ketone Enolate Anions
title Synthesis of Benzo-Fused Heterocycles by Intramolecular alpha-Arylation of Ketone Enolate Anions
spellingShingle Synthesis of Benzo-Fused Heterocycles by Intramolecular alpha-Arylation of Ketone Enolate Anions
Guastavino, Javier Fernando
Benzo-Fused Heterocycles
Srn1 Reactions
Ketone Enolate Anions
Arylation
Alpha-Aryl Ketone
title_short Synthesis of Benzo-Fused Heterocycles by Intramolecular alpha-Arylation of Ketone Enolate Anions
title_full Synthesis of Benzo-Fused Heterocycles by Intramolecular alpha-Arylation of Ketone Enolate Anions
title_fullStr Synthesis of Benzo-Fused Heterocycles by Intramolecular alpha-Arylation of Ketone Enolate Anions
title_full_unstemmed Synthesis of Benzo-Fused Heterocycles by Intramolecular alpha-Arylation of Ketone Enolate Anions
title_sort Synthesis of Benzo-Fused Heterocycles by Intramolecular alpha-Arylation of Ketone Enolate Anions
dc.creator.none.fl_str_mv Guastavino, Javier Fernando
Rossi, Roberto Arturo
author Guastavino, Javier Fernando
author_facet Guastavino, Javier Fernando
Rossi, Roberto Arturo
author_role author
author2 Rossi, Roberto Arturo
author2_role author
dc.subject.none.fl_str_mv Benzo-Fused Heterocycles
Srn1 Reactions
Ketone Enolate Anions
Arylation
Alpha-Aryl Ketone
topic Benzo-Fused Heterocycles
Srn1 Reactions
Ketone Enolate Anions
Arylation
Alpha-Aryl Ketone
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A two-step synthesis of six-, seven-, eight-, and nine-member benzo-fused heterocycles in good to excellent yields is reported. The synthetic strategy involves the generation of a new intramolecular alpha-aryl ketone bond by the photostimulated SRN1 reaction of ketone enolate anions linked to a pendant haloarene as the key step. On the other hand, an intramolecular CAr-CAr coupling led to the formation of five- and six-member benzo-fused heterocycles (9H-carbazole and phenanthridine) when an aromatic amide anion is competitively formed
Fil: Guastavino, Javier Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química (i); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto de Investigaciones en Físicoquímica de Córdoba; Argentina. Universidad Nacional de Córdoba; Argentina
Fil: Rossi, Roberto Arturo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto de Investigaciones en Físicoquímica de Córdoba; Argentina. Universidad Nacional de Córdoba; Argentina
description A two-step synthesis of six-, seven-, eight-, and nine-member benzo-fused heterocycles in good to excellent yields is reported. The synthetic strategy involves the generation of a new intramolecular alpha-aryl ketone bond by the photostimulated SRN1 reaction of ketone enolate anions linked to a pendant haloarene as the key step. On the other hand, an intramolecular CAr-CAr coupling led to the formation of five- and six-member benzo-fused heterocycles (9H-carbazole and phenanthridine) when an aromatic amide anion is competitively formed
publishDate 2012
dc.date.none.fl_str_mv 2012-01
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/11336/10963
Guastavino, Javier Fernando; Rossi, Roberto Arturo; Synthesis of Benzo-Fused Heterocycles by Intramolecular alpha-Arylation of Ketone Enolate Anions; American Chemical Society; Journal Of Organic Chemistry; 77; 1; 1-2012; 460-472
0022-3263
url http://hdl.handle.net/11336/10963
identifier_str_mv Guastavino, Javier Fernando; Rossi, Roberto Arturo; Synthesis of Benzo-Fused Heterocycles by Intramolecular alpha-Arylation of Ketone Enolate Anions; American Chemical Society; Journal Of Organic Chemistry; 77; 1; 1-2012; 460-472
0022-3263
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/jo202012n
info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/jo202012n
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
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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 13.070432

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