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Synthesis, structure and NMR study of fluorinated isoxazoles derived from hemi-curcuminoids

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dc.contributor.authorNieto Gómez, Carla Isabel
dc.contributor.authorCornago, María del Pilar
dc.contributor.authorCabildo, María del Pilar
dc.contributor.authorSanz del Castillo, Dionisia
dc.contributor.authorClaramunt Vallespí, Rosa María
dc.contributor.authorElguero, José
dc.date.accessioned2024-08-28T12:05:20Z
dc.date.available2024-08-28T12:05:20Z
dc.date.issued2019-03
dc.descriptionThis is an Accepted Manuscript of an article published in “Journal of Fluorine Chemistry, 219, 39-49", is available online at the publisher's website: Elsevier, https://doi.org/10.1016/j.jfluchem.2018.12.012
dc.descriptionEste es el manuscrito aceptado del artículo publicado en “Journal of Fluorine Chemistry, 219, 39-49", disponible en línea en el sitio web del editor: Elsevier, https://doi.org/10.1016/j.jfluchem.2018.12.012
dc.description.abstractThe purpose of this work is to prepare a series of isoxazoles bearing phenyl and 4'-hydroxy-styryl substituents at position 3 and 5; besides the phenyl group of the styryl residue bears one or two fluorine substituents. They were prepared to study their structure in the solid state and in solution by X-ray crystallography and solid-state NMR (SSNMR) for the solid state and NMR for the solution. The reaction of hydroxylamine with hemi-curcuminoid β-diketones affords two isomeric isoxazoles we have named series a (3-phenyl) and b (5-phenyl) that have been identified and characterized. Four pairs have been prepared that in three cases bear one or two fluorine atoms. Three X-ray structures have been determined 3a, 3b and 5b; 3a crystallizes without solvent, 3b crystallizes with a water molecule hydrogen-bonded to a phenolic OH, finally 5b crystallizes as a solvate with a methanol molecule hydrogen-bonded to the isoxazole N atom. This hydrogen bond results in larger differences between 15N chemical shifts in DMSO-d6 solution and in the solid state. The splitting of some signals observed in Cross-Polarization Magic Angle Spinning (CPMAS) 13C NMR was assigned to 1JCF dipolar couplings. The combined use of crystallography and SSNMR affords a complete characterization of isomeric isoxazoles, in particular the assignment of an isoxazole to a or to b series is not a trivial matter. In this work, we describe methods for the synthesis of isoxazoles bearing fluorine substituents that are promising structures for drug discovery.en
dc.description.versionversión final
dc.identifier.citationNieto, C. I., Cornago, M. P., Cabildo, M. P., Sanz, D., Claramunt, R. M., Torralba, M. C., & Elguero, J. (2019). Synthesis, structure and NMR study of fluorinated isoxazoles derived from hemi-curcuminoids. Journal of Fluorine Chemistry, 219, 39-49. https://doi.org/10.1016/J.JFLUCHEM.2018.12.012
dc.identifier.doihttps://doi.org/10.1016/j.jfluchem.2018.12.012
dc.identifier.issn0022-1139
dc.identifier.urihttps://hdl.handle.net/20.500.14468/23575
dc.journal.titleJournal of Fluorine Chemistry
dc.journal.volume209
dc.language.isoen
dc.page.final49
dc.page.initial39
dc.publisherElsevier
dc.relation.centerFacultades y escuelas::Facultad de Ciencias
dc.relation.departmentQuímica Orgánica y Bio-Orgánica
dc.rightsinfo:eu-repo/semantics/openAccess
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/deed.es
dc.subject23 Química::2306 Química orgánica
dc.subject.keywordsIsoxazoleen
dc.subject.keywordsHemi-curcuminoidsen
dc.subject.keywordsFluorinated isoxazolesen
dc.subject.keywordsSolid-state NMRen
dc.subject.keywordsX-ray crystallographyen
dc.titleSynthesis, structure and NMR study of fluorinated isoxazoles derived from hemi-curcuminoidsen
dc.typeartículoes
dc.typejournal articleen
dspace.entity.typePublication
relation.isAuthorOfPublicationc6f94a2a-9f54-48f9-a6f1-3115b17b098d
relation.isAuthorOfPublicationc4e6468b-75c5-452b-bf12-9637dd3519f3
relation.isAuthorOfPublication.latestForDiscoveryc6f94a2a-9f54-48f9-a6f1-3115b17b098d
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