Artículo
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.; Fortes, Margiani P.; Back, Davi F.; Kaufman, Teodoro Saul
; Silveira, Claudio C.
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Fecha de publicación:
11/2014
Editorial:
Royal Society of Chemistry
Revista:
RSC Advances
ISSN:
2046-2069
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
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.
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Articulos(IQUIR)
Articulos de INST.DE QUIMICA ROSARIO
Articulos de INST.DE QUIMICA ROSARIO
Citación
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
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