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dc.contributor.author
Bassaco, Mariana M.
dc.contributor.author
Fortes, Margiani P.
dc.contributor.author
Back, Davi F.
dc.contributor.author
Kaufman, Teodoro Saul
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dc.contributor.author
Silveira, Claudio C.
dc.date.available
2016-06-06T20:54:24Z
dc.date.issued
2014-11
dc.identifier.citation
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
dc.identifier.issn
2046-2069
dc.identifier.uri
http://hdl.handle.net/11336/6053
dc.description.abstract
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.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Royal Society of Chemistry
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dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.subject
Chemical Synthesis-Methodology
dc.subject
3,5-Disubstituted 1,2-Oxazoles
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1,3-Diynes
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Reaction Mechanisms
dc.subject.classification
Química Orgánica
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.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
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2016-06-01T13:36:19Z
dc.journal.volume
4
dc.journal.number
105
dc.journal.pagination
60785-60797
dc.journal.pais
Reino Unido
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dc.journal.ciudad
Londres
dc.description.fil
Fil: Bassaco, Mariana M.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
dc.description.fil
Fil: Fortes, Margiani P.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
dc.description.fil
Fil: Back, Davi F.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
dc.description.fil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
dc.description.fil
Fil: Silveira, Claudio C.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
dc.journal.title
RSC Advances
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2014/RA/c4ra11571f
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1039/C4RA11571F
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