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Advisor(s)
Abstract(s)
Xanthones and 1,2,3-triazoles are known to exhibit several biological, pharmacological and biocidal
properties[1]. The potential applications of these two classes of heterocycles led us to develop new
strategies to synthesize xanthone-1,2,3-triazole dyads, aiming to get potentially improved therapeutic
agents[2]. With this rational in mind we designed and synthesized novel chromone derivatives 1a-d to be
used as building motifs and to explore the reactivity of the two unsaturated systems (the diene and the
alkyne). In the present communication we will present a new synthetic route towards the synthesis of
xanthone-1,2,3-triazole dyads 7a-d using consecutively the azide-alkyne Huisgen 1,3-dipolar
cycloaddition and Diels-Alder reaction. Our approach involves the synthesis chromone-triazole
derivatives 2a-d using the reaction of 1a-d with sodium azide, followed by the methylation of the NH of
the triazole moiety. The methylation afforded three isomers 3a-d, 4a-d and 5a-d, as expected. The major
isomers 3a-d were used in the Diels-Alder reaction with N-methylmaleimide, and the adducts obtained
6a-d were oxidized to afford the xanthone-1,2,3-triazole dyads 7a-d. All the synthetic details as well as
the structural characterization (by 1D and 2D NMR studies) of the new synthesised compounds will be
presented and discussed.
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Citation
Albuquerque, Hélio; Santos, Clementina M.M.; Silva, Artur; Cavaleiro, José (2015). Synthesis of xanthone-1,2,3-triazole dyads. In 19th European Symposium on Organic Chemistry. Lisboa