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A Synthetic Approach to PW2‐Like Compounds
Author(s) -
Forastieri Pamela S.,
Luna Liliana E.,
Cravero Raquel M.,
Labadie Guillermo R.
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201903654
Subject(s) - aromatization , chemistry , amide , benzylamine , moiety , acetic acid , organic chemistry , cerium , alkyl , xanthene , hydrolysis , combinatorial chemistry , catalysis
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.