SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes

Autores
Martins, Guilherme M.; Back, Davi Fernando; Kaufman, Teodoro Saul; Silveira, Claudio
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A novel and efficient SeCl2-mediated chalcogenative cyclization strategy toward 3-selenophen-3-yl-1H-indoles from readily available and conveniently substituted propargyl indoles is described. It entails an unprecedented selenirenium-induced 1,2-indolyl shift prompted by the electrophilic addition of SeCl2 to the triple bond of the propargyl indole, followed by cyclization through the intermediacy of a 1-seleno-1,3-diene. The reaction takes place at room temperature and shows excellent selectivity, broad substrate scope, and wide functional group tolerance.
Fil: Martins, Guilherme M.. Universidade Federal de Santa Maria; Brasil
Fil: Back, Davi Fernando. Universidade Federal de Santa Maria; Brasil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Silveira, Claudio. Universidade Federal de Santa Maria; Brasil
Materia
heterocycles
indolo[2,3-b]selenophenes
substituted selenophenes
arylacetylenes
cyclization
SeCl2
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:11336/87286
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted SelenophenesMartins, Guilherme M.Back, Davi FernandoKaufman, Teodoro SaulSilveira, Claudioheterocyclesindolo[2,3-b]selenophenessubstituted selenophenesarylacetylenescyclizationSeCl2https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A novel and efficient SeCl2-mediated chalcogenative cyclization strategy toward 3-selenophen-3-yl-1H-indoles from readily available and conveniently substituted propargyl indoles is described. It entails an unprecedented selenirenium-induced 1,2-indolyl shift prompted by the electrophilic addition of SeCl2 to the triple bond of the propargyl indole, followed by cyclization through the intermediacy of a 1-seleno-1,3-diene. The reaction takes place at room temperature and shows excellent selectivity, broad substrate scope, and wide functional group tolerance.Fil: Martins, Guilherme M.. Universidade Federal de Santa Maria; BrasilFil: Back, Davi Fernando. Universidade Federal de Santa Maria; BrasilFil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Silveira, Claudio. Universidade Federal de Santa Maria; BrasilAmerican Chemical Society2018-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/87286Martins, Guilherme M.; Back, Davi Fernando; Kaufman, Teodoro Saul; Silveira, Claudio; SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes; American Chemical Society; Journal of Organic Chemistry; 83; 6; 3-2018; 3252-32640022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/10.1021/acs.joc.8b00166info:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.8b00166info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:40:05Zoai:ri.conicet.gov.ar:11336/87286instacron: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 10:40:06.22CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes
title SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes
spellingShingle SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes
Martins, Guilherme M.
heterocycles
indolo[2,3-b]selenophenes
substituted selenophenes
arylacetylenes
cyclization
SeCl2
title_short SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes
title_full SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes
title_fullStr SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes
title_full_unstemmed SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes
title_sort SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes
dc.creator.none.fl_str_mv Martins, Guilherme M.
Back, Davi Fernando
Kaufman, Teodoro Saul
Silveira, Claudio
author Martins, Guilherme M.
author_facet Martins, Guilherme M.
Back, Davi Fernando
Kaufman, Teodoro Saul
Silveira, Claudio
author_role author
author2 Back, Davi Fernando
Kaufman, Teodoro Saul
Silveira, Claudio
author2_role author
author
author
dc.subject.none.fl_str_mv heterocycles
indolo[2,3-b]selenophenes
substituted selenophenes
arylacetylenes
cyclization
SeCl2
topic heterocycles
indolo[2,3-b]selenophenes
substituted selenophenes
arylacetylenes
cyclization
SeCl2
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 novel and efficient SeCl2-mediated chalcogenative cyclization strategy toward 3-selenophen-3-yl-1H-indoles from readily available and conveniently substituted propargyl indoles is described. It entails an unprecedented selenirenium-induced 1,2-indolyl shift prompted by the electrophilic addition of SeCl2 to the triple bond of the propargyl indole, followed by cyclization through the intermediacy of a 1-seleno-1,3-diene. The reaction takes place at room temperature and shows excellent selectivity, broad substrate scope, and wide functional group tolerance.
Fil: Martins, Guilherme M.. Universidade Federal de Santa Maria; Brasil
Fil: Back, Davi Fernando. Universidade Federal de Santa Maria; Brasil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Silveira, Claudio. Universidade Federal de Santa Maria; Brasil
description A novel and efficient SeCl2-mediated chalcogenative cyclization strategy toward 3-selenophen-3-yl-1H-indoles from readily available and conveniently substituted propargyl indoles is described. It entails an unprecedented selenirenium-induced 1,2-indolyl shift prompted by the electrophilic addition of SeCl2 to the triple bond of the propargyl indole, followed by cyclization through the intermediacy of a 1-seleno-1,3-diene. The reaction takes place at room temperature and shows excellent selectivity, broad substrate scope, and wide functional group tolerance.
publishDate 2018
dc.date.none.fl_str_mv 2018-03
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/11336/87286
Martins, Guilherme M.; Back, Davi Fernando; Kaufman, Teodoro Saul; Silveira, Claudio; SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes; American Chemical Society; Journal of Organic Chemistry; 83; 6; 3-2018; 3252-3264
0022-3263
CONICET Digital
CONICET
url http://hdl.handle.net/11336/87286
identifier_str_mv Martins, Guilherme M.; Back, Davi Fernando; Kaufman, Teodoro Saul; Silveira, Claudio; SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes; American Chemical Society; Journal of Organic Chemistry; 83; 6; 3-2018; 3252-3264
0022-3263
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/10.1021/acs.joc.8b00166
info:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.8b00166
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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