A synthetic approach to PW2‐Like compounds

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dc.citation.titleChemistrySelectes
dc.citation.volume5(5)es
dc.creatorForastieri, Pamela S.
dc.creatorLuna, Liliana E.
dc.creatorCravero, Raquel M.
dc.creatorLabadie, Guillermo Roberto
dc.date.accessioned2020-05-27T21:05:21Z
dc.date.available2020-05-27T21:05:21Z
dc.date.issued2020-02-05
dc.descriptionThe 9H‐xanthene derivatives, like PW2, displayed a wide spectrum of bioactivities. Herein, we reported a rapid and simple synthetic route for compounds containing the xanthenic moiety in their structure and amides. The efficient preparation of novel 1,8‐dioxo‐2,3,4,5,6,7,8,9‐octahydro‐1‐xanthen‐9‐yl‐ acetic acid alkyl esters by multicomponent tandem Michael‐cyclization reactions starting from cyclohexanediones and alkynes is described. Iodine and cerium (IV) ammonium nitrate were used for the oxidative aromatization step proving a series of 1,8‐mono and dialkoxy‐alkyl‐xanthenyl‐9‐yl acetic acid esters in good yields. The proposed mechanism for the oxidative aromatization involves several organic transformations. The final step was the incorporation of an amide to mimic the PW2 structure that was prepared by hydrolysis of the esters, followed by the amide formation using N,N ‐dimethyl‐1,3‐ propandiamine, and benzylamine.es
dc.description.filFil: Forastieri, Pamela S. Universidad Nacional del Rosario. Facultad de Ciencias Bioquímicas y Farmaceúticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina.es
dc.description.filFil: Luna, Liliana E. Universidad Nacional del Rosario. Facultad de Ciencias Bioquímicas y Farmaceúticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina.es
dc.description.filFil: Cravero, Raquel M. Universidad Nacional del Rosario. Facultad de Ciencias Bioquímicas y Farmaceúticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina.es
dc.description.filFil: Labadie, Guillermo Roberto. Universidad Nacional del Rosario. Facultad de Ciencias Bioquímicas y Farmaceúticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina.es
dc.description.sponsorshipUniversidad Nacional de Rosario (UNR): Grant Number 1BIO303 19/B450es
dc.description.sponsorshipConsejo Nacional de Investigaciones Científicas y Técnicas (CONICET): Grant Number 11220110100448es
dc.formatapplication/pdf
dc.format.extent1776-1780es
dc.identifier.issn2365-6549es
dc.identifier.urihttp://hdl.handle.net/2133/18272
dc.language.isoenges
dc.publisherWileyes
dc.relation.publisherversionhttps://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/slct.201903654es
dc.relation.publisherversionhttps://doi.org/10.1002/slct.201903654es
dc.rightsembargoedAccesses
dc.rights.holderWileyes
dc.rights.holderForastieri, Pamela S.es
dc.rights.holderLuna, Liliana E.es
dc.rights.holderCravero , Raquel M.es
dc.rights.holderLabadie, Guillermo Robertoes
dc.rights.holderUniversidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticases
dc.rights.textAtribución-NoComercial-SinDerivadas 4.0 Internacional (CC BY-NC-ND 4.0)es
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/deed.es*
dc.subject1,8-alkoxy-9H-Xanthen-9-yl-acetic acid alkyl estersamideses
dc.subjectIodine oxidative aromatizationes
dc.subjectMulticomponent reactionses
dc.subjectPW2es
dc.subjectAmideses
dc.titleA synthetic approach to PW2‐Like compoundses
dc.typearticle
dc.typeartículo
dc.typepublishedVersion
dc.type.collectionarticulo
dc.type.versionpublishedVersiones

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