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

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 pend...

ver descrição completa

Detalhes bibliográficos
Autores: Guastavino, Javier Fernando, Rossi, Roberto Arturo
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2012
País:Argentina
Recursos:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/10963
Acesso em linha:http://hdl.handle.net/11336/10963
Access Level:acceso abierto
Palavra-chave:Benzo-Fused Heterocycles
Srn1 Reactions
Ketone Enolate Anions
Arylation
Alpha-Aryl Ketone
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
id AR_ca40a3cd831a065bf6d307a178a078a6
oai_identifier_str oai:ri.conicet.gov.ar:11336/10963
network_acronym_str AR
network_name_str Argentina
repository_id_str
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 Técnicas2024-05-08T13:32:31Zoai: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:34982024-05-08 13:32:31.206CONICET 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
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic Benzo-Fused Heterocycles
Srn1 Reactions
Ketone Enolate Anions
Arylation
Alpha-Aryl Ketone
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
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_ 1799194596991827968
score 15,812429

Registos relacionados