A synthetic approach to PW2‐Like compounds

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...

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Autores principales: Forastieri, Pamela S., Luna, Liliana E., Cravero, Raquel M., Labadie, Guillermo Roberto
Formato: article artículo publishedVersion
Lenguaje:Inglés
Publicado: Wiley 2020
Materias:
1,8-alkoxy-9H-Xanthen-9-yl-acetic acid alkyl estersamides
Iodine oxidative aromatization
Multicomponent reactions
PW2
Amides
Acceso en línea:http://hdl.handle.net/2133/18272
http://hdl.handle.net/2133/18272
Aporte de:
Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR) de Universidad Nacional de Rosario
id I15-R121-2133-18272
record_format dspace
institution Universidad Nacional de Rosario
institution_str I-15
repository_str R-121
collection Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR)
language Inglés
orig_language_str_mv eng
topic 1,8-alkoxy-9H-Xanthen-9-yl-acetic acid alkyl estersamides
Iodine oxidative aromatization
Multicomponent reactions
PW2
Amides
spellingShingle 1,8-alkoxy-9H-Xanthen-9-yl-acetic acid alkyl estersamides
Iodine oxidative aromatization
Multicomponent reactions
PW2
Amides
Forastieri, Pamela S.
Luna, Liliana E.
Cravero, Raquel M.
Labadie, Guillermo Roberto
A synthetic approach to PW2‐Like compounds
topic_facet 1,8-alkoxy-9H-Xanthen-9-yl-acetic acid alkyl estersamides
Iodine oxidative aromatization
Multicomponent reactions
PW2
Amides
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.
format article
artículo
publishedVersion
author Forastieri, Pamela S.
Luna, Liliana E.
Cravero, Raquel M.
Labadie, Guillermo Roberto
author_facet Forastieri, Pamela S.
Luna, Liliana E.
Cravero, Raquel M.
Labadie, Guillermo Roberto
author_sort Forastieri, Pamela S.
title A synthetic approach to PW2‐Like compounds
title_short A synthetic approach to PW2‐Like compounds
title_full A synthetic approach to PW2‐Like compounds
title_fullStr A synthetic approach to PW2‐Like compounds
title_full_unstemmed A synthetic approach to PW2‐Like compounds
title_sort synthetic approach to pw2‐like compounds
publisher Wiley
publishDate 2020
url http://hdl.handle.net/2133/18272
http://hdl.handle.net/2133/18272
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