A synthetic approach to PW2‐Like compounds

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dc.creator Forastieri, Pamela S.
dc.creator Luna, Liliana E.
dc.creator Cravero, Raquel M.
dc.creator Labadie, Guillermo Roberto
dc.date.accessioned 2020-05-27T21:05:21Z
dc.date.available 2020-05-27T21:05:21Z
dc.date.issued 2020-02-05
dc.identifier.issn 2365-6549 es
dc.identifier.uri http://hdl.handle.net/2133/18272
dc.description The 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.sponsorship Universidad Nacional de Rosario (UNR): Grant Number 1BIO303 19/B450 es
dc.description.sponsorship Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET): Grant Number 11220110100448 es
dc.format application/pdf
dc.format.extent 1776-1780 es
dc.language.iso eng es
dc.publisher Wiley es
dc.rights embargoedAccess es
dc.rights.uri https://creativecommons.org/licenses/by-nc-nd/4.0/deed.es *
dc.subject 1,8-alkoxy-9H-Xanthen-9-yl-acetic acid alkyl estersamides es
dc.subject Iodine oxidative aromatization es
dc.subject Multicomponent reactions es
dc.subject PW2 es
dc.subject Amides es
dc.title A synthetic approach to PW2‐Like compounds es
dc.type article
dc.type artículo
dc.type publishedVersion
dc.rights.holder Wiley es
dc.rights.holder Forastieri, Pamela S. es
dc.rights.holder Luna, Liliana E. es
dc.rights.holder Cravero , Raquel M. es
dc.rights.holder Labadie, Guillermo Roberto es
dc.rights.holder Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas es
dc.relation.publisherversion https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/slct.201903654 es
dc.relation.publisherversion https://doi.org/10.1002/slct.201903654 es
dc.rights.text Atribución-NoComercial-SinDerivadas 4.0 Internacional (CC BY-NC-ND 4.0) es
dc.citation.title ChemistrySelect es
dc.citation.volume 5(5) es
dc.description.fil Fil: Forastieri, Pamela S. Universidad Nacional del Rosario. Facultad de Ciencias Bioquímicas y Farmaceúticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina. es
dc.description.fil Fil: Luna, Liliana E. Universidad Nacional del Rosario. Facultad de Ciencias Bioquímicas y Farmaceúticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina. es
dc.description.fil Fil: Cravero, Raquel M. Universidad Nacional del Rosario. Facultad de Ciencias Bioquímicas y Farmaceúticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina. es
dc.description.fil Fil: Labadie, Guillermo Roberto. Universidad Nacional del Rosario. Facultad de Ciencias Bioquímicas y Farmaceúticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina. es
dc.type.collection articulo
dc.type.version publishedVersion es


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