An Eco-friendly Synthesis of Novel 3,5-Disubstituted-1,2-isoxazoles in PEG-400, Employing the Et3N-Promoted Hydroamination of Symmetric and Unsymmetric 1,3-Diyne-indole Derivatives

Autores
Bassaco, Mariana M.; Fortes, Margiani P.; Back, Davi F.; Kaufman, Teodoro Saul; Silveira, Claudio C.
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A facile, efficient and atom-economic synthesis of 3,5-disubstituted 1,2-isoxazoles bearing indole moieties, is reported. The synthesis of these isoxazoles was carried out by the triethylamine-promoted reaction of symmetric and unsymmetric 1,3-diyne indole derivatives with hydroxylamine in PEG-400, as an eco-friendly solvent, under relatively mild conditions. The synthesis of the starting 1,3-diyne indole derivatives was performed by the aerobic self-coupling of diversely functionalized N-propargyl indoles and N-propargyl carbazole under copper catalysis, or by the reaction of the propargyl derivatives with phenyl- or p-tolyl-acetylene under combined nickel and copper catalysis. The isoxazolation reaction was optimized, its scope and limitations were studied and a detailed reaction mechanism was proposed.
Fil: Bassaco, Mariana M.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
Fil: Fortes, Margiani P.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
Fil: Back, Davi F.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Silveira, Claudio C.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
Materia
Chemical Synthesis-Methodology
3,5-Disubstituted 1,2-Oxazoles
1,3-Diynes
Reaction Mechanisms
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/6053
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling An Eco-friendly Synthesis of Novel 3,5-Disubstituted-1,2-isoxazoles in PEG-400, Employing the Et3N-Promoted Hydroamination of Symmetric and Unsymmetric 1,3-Diyne-indole DerivativesBassaco, Mariana M.Fortes, Margiani P.Back, Davi F.Kaufman, Teodoro SaulSilveira, Claudio C.Chemical Synthesis-Methodology3,5-Disubstituted 1,2-Oxazoles1,3-DiynesReaction Mechanismshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A facile, efficient and atom-economic synthesis of 3,5-disubstituted 1,2-isoxazoles bearing indole moieties, is reported. The synthesis of these isoxazoles was carried out by the triethylamine-promoted reaction of symmetric and unsymmetric 1,3-diyne indole derivatives with hydroxylamine in PEG-400, as an eco-friendly solvent, under relatively mild conditions. The synthesis of the starting 1,3-diyne indole derivatives was performed by the aerobic self-coupling of diversely functionalized N-propargyl indoles and N-propargyl carbazole under copper catalysis, or by the reaction of the propargyl derivatives with phenyl- or p-tolyl-acetylene under combined nickel and copper catalysis. The isoxazolation reaction was optimized, its scope and limitations were studied and a detailed reaction mechanism was proposed.Fil: Bassaco, Mariana M.. Universidade Federal de Santa Maria. Departamento de Química; BrasilFil: Fortes, Margiani P.. Universidade Federal de Santa Maria. Departamento de Química; BrasilFil: Back, Davi F.. Universidade Federal de Santa Maria. Departamento de Química; BrasilFil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Silveira, Claudio C.. Universidade Federal de Santa Maria. Departamento de Química; BrasilRoyal Society of Chemistry2014-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/6053Bassaco, Mariana M.; Fortes, Margiani P.; Back, Davi F.; Kaufman, Teodoro Saul; Silveira, Claudio C.; An Eco-friendly Synthesis of Novel 3,5-Disubstituted-1,2-isoxazoles in PEG-400, Employing the Et3N-Promoted Hydroamination of Symmetric and Unsymmetric 1,3-Diyne-indole Derivatives; Royal Society of Chemistry; RSC Advances; 4; 105; 11-2014; 60785-607972046-2069enginfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2014/RA/c4ra11571finfo:eu-repo/semantics/altIdentifier/doi/10.1039/C4RA11571Finfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:04:33Zoai:ri.conicet.gov.ar:11336/6053instacron: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:34982025-09-03 10:04:33.968CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv An Eco-friendly Synthesis of Novel 3,5-Disubstituted-1,2-isoxazoles in PEG-400, Employing the Et3N-Promoted Hydroamination of Symmetric and Unsymmetric 1,3-Diyne-indole Derivatives
title An Eco-friendly Synthesis of Novel 3,5-Disubstituted-1,2-isoxazoles in PEG-400, Employing the Et3N-Promoted Hydroamination of Symmetric and Unsymmetric 1,3-Diyne-indole Derivatives
spellingShingle An Eco-friendly Synthesis of Novel 3,5-Disubstituted-1,2-isoxazoles in PEG-400, Employing the Et3N-Promoted Hydroamination of Symmetric and Unsymmetric 1,3-Diyne-indole Derivatives
Bassaco, Mariana M.
Chemical Synthesis-Methodology
3,5-Disubstituted 1,2-Oxazoles
1,3-Diynes
Reaction Mechanisms
title_short An Eco-friendly Synthesis of Novel 3,5-Disubstituted-1,2-isoxazoles in PEG-400, Employing the Et3N-Promoted Hydroamination of Symmetric and Unsymmetric 1,3-Diyne-indole Derivatives
title_full An Eco-friendly Synthesis of Novel 3,5-Disubstituted-1,2-isoxazoles in PEG-400, Employing the Et3N-Promoted Hydroamination of Symmetric and Unsymmetric 1,3-Diyne-indole Derivatives
title_fullStr An Eco-friendly Synthesis of Novel 3,5-Disubstituted-1,2-isoxazoles in PEG-400, Employing the Et3N-Promoted Hydroamination of Symmetric and Unsymmetric 1,3-Diyne-indole Derivatives
title_full_unstemmed An Eco-friendly Synthesis of Novel 3,5-Disubstituted-1,2-isoxazoles in PEG-400, Employing the Et3N-Promoted Hydroamination of Symmetric and Unsymmetric 1,3-Diyne-indole Derivatives
title_sort An Eco-friendly Synthesis of Novel 3,5-Disubstituted-1,2-isoxazoles in PEG-400, Employing the Et3N-Promoted Hydroamination of Symmetric and Unsymmetric 1,3-Diyne-indole Derivatives
dc.creator.none.fl_str_mv Bassaco, Mariana M.
Fortes, Margiani P.
Back, Davi F.
Kaufman, Teodoro Saul
Silveira, Claudio C.
author Bassaco, Mariana M.
author_facet Bassaco, Mariana M.
Fortes, Margiani P.
Back, Davi F.
Kaufman, Teodoro Saul
Silveira, Claudio C.
author_role author
author2 Fortes, Margiani P.
Back, Davi F.
Kaufman, Teodoro Saul
Silveira, Claudio C.
author2_role author
author
author
author
dc.subject.none.fl_str_mv Chemical Synthesis-Methodology
3,5-Disubstituted 1,2-Oxazoles
1,3-Diynes
Reaction Mechanisms
topic Chemical Synthesis-Methodology
3,5-Disubstituted 1,2-Oxazoles
1,3-Diynes
Reaction Mechanisms
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 facile, efficient and atom-economic synthesis of 3,5-disubstituted 1,2-isoxazoles bearing indole moieties, is reported. The synthesis of these isoxazoles was carried out by the triethylamine-promoted reaction of symmetric and unsymmetric 1,3-diyne indole derivatives with hydroxylamine in PEG-400, as an eco-friendly solvent, under relatively mild conditions. The synthesis of the starting 1,3-diyne indole derivatives was performed by the aerobic self-coupling of diversely functionalized N-propargyl indoles and N-propargyl carbazole under copper catalysis, or by the reaction of the propargyl derivatives with phenyl- or p-tolyl-acetylene under combined nickel and copper catalysis. The isoxazolation reaction was optimized, its scope and limitations were studied and a detailed reaction mechanism was proposed.
Fil: Bassaco, Mariana M.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
Fil: Fortes, Margiani P.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
Fil: Back, Davi F.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Silveira, Claudio C.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
description A facile, efficient and atom-economic synthesis of 3,5-disubstituted 1,2-isoxazoles bearing indole moieties, is reported. The synthesis of these isoxazoles was carried out by the triethylamine-promoted reaction of symmetric and unsymmetric 1,3-diyne indole derivatives with hydroxylamine in PEG-400, as an eco-friendly solvent, under relatively mild conditions. The synthesis of the starting 1,3-diyne indole derivatives was performed by the aerobic self-coupling of diversely functionalized N-propargyl indoles and N-propargyl carbazole under copper catalysis, or by the reaction of the propargyl derivatives with phenyl- or p-tolyl-acetylene under combined nickel and copper catalysis. The isoxazolation reaction was optimized, its scope and limitations were studied and a detailed reaction mechanism was proposed.
publishDate 2014
dc.date.none.fl_str_mv 2014-11
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/11336/6053
Bassaco, Mariana M.; Fortes, Margiani P.; Back, Davi F.; Kaufman, Teodoro Saul; Silveira, Claudio C.; An Eco-friendly Synthesis of Novel 3,5-Disubstituted-1,2-isoxazoles in PEG-400, Employing the Et3N-Promoted Hydroamination of Symmetric and Unsymmetric 1,3-Diyne-indole Derivatives; Royal Society of Chemistry; RSC Advances; 4; 105; 11-2014; 60785-60797
2046-2069
url http://hdl.handle.net/11336/6053
identifier_str_mv Bassaco, Mariana M.; Fortes, Margiani P.; Back, Davi F.; Kaufman, Teodoro Saul; Silveira, Claudio C.; An Eco-friendly Synthesis of Novel 3,5-Disubstituted-1,2-isoxazoles in PEG-400, Employing the Et3N-Promoted Hydroamination of Symmetric and Unsymmetric 1,3-Diyne-indole Derivatives; Royal Society of Chemistry; RSC Advances; 4; 105; 11-2014; 60785-60797
2046-2069
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2014/RA/c4ra11571f
info:eu-repo/semantics/altIdentifier/doi/10.1039/C4RA11571F
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.format.none.fl_str_mv 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 13.13397

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