Deacylative alkylation (DaA) of N-methyl-3-acetyl-2-oxindole for the synthesis of symmetrically 3,3-disubstituted 2-oxindoles. An access gate to anticancer agents and natural products

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dc.contributorSíntesis Asimétrica (SINTAS)es_ES
dc.contributor.authorMoreno-Cabrerizo, Cristina-
dc.contributor.authorOrtega-Martínez, Aitor-
dc.contributor.authorMolina, Cynthia-
dc.contributor.authorNájera, Carmen-
dc.contributor.authorSansano, Jose M.-
dc.contributor.otherUniversidad de Alicante. Departamento de Química Orgánicaes_ES
dc.contributor.otherUniversidad de Alicante. Instituto Universitario de Síntesis Orgánicaes_ES
dc.date.accessioned2018-06-08T07:48:45Z-
dc.date.available2018-06-08T07:48:45Z-
dc.date.issued2018-
dc.identifier.citationAnais da Academia Brasileira de Ciências. 2018, 90(1 Suppl. 2): 1089-1099. doi:10.1590/0001-3765201820170783es_ES
dc.identifier.issn0001-3765-
dc.identifier.issn1678-2690 (Online)-
dc.identifier.urihttp://hdl.handle.net/10045/76371-
dc.description.abstractThe synthesis of 3,3-disubstituted N-methyloxindoles, starting from 3-acetyl-2-hydroxy-1-methyloxindole employing a sequential one-pot synthesis, is studied. The process involves a first alkylation in the presence of 1 equiv. of both organic halide and Triton B and the second one employs another 1.5 equiv. of each in moderate to high yields. This procedure is compared with the results obtained from the direct dialkylation of N-methyloxindole. The metathesis of one of the corresponding diallylated product was also studied obtaining the spiranic oxindole. All these methodologies are directed towards the access to anticancer agents and natural biologically active products.es_ES
dc.description.sponsorshipFinancial support was provided by the Spanish Ministerio de Economía y Competitividad (MINECO) (projects CTQ2013-43446-P and CTQ2014-51912-REDC), the Spanish Ministerio de Economía, Industria y Competitividad, Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects CTQ2016-76782-P and CTQ2016-81797-REDC), by the Generalitat Valenciana (PROMETEO2009/039 and PROMETEOII/ 2014/017) and by the University of Alicante. Aitor Ortega-Martínez thanks MINECO for a predoctoral fellowship.es_ES
dc.languageenges_ES
dc.publisherAcademia Brasileira de Ciênciases_ES
dc.rightsCreative Commons Attribution Licensees_ES
dc.subjectDeacylationes_ES
dc.subjectAlkylationes_ES
dc.subject2-oxindoleses_ES
dc.subjectMetathesises_ES
dc.subjectAnticanceres_ES
dc.subjectNatural productses_ES
dc.subject.otherQuímica Orgánicaes_ES
dc.titleDeacylative alkylation (DaA) of N-methyl-3-acetyl-2-oxindole for the synthesis of symmetrically 3,3-disubstituted 2-oxindoles. An access gate to anticancer agents and natural productses_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.peerreviewedsies_ES
dc.identifier.doi10.1590/0001-3765201820170783-
dc.relation.publisherversionhttps://doi.org/10.1590/0001-3765201820170783es_ES
dc.rights.accessRightsinfo:eu-repo/semantics/openAccesses_ES
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