synthetic strategies to 2'-hydroxy-4'-methylsulfonylacetophenone, a key compound for the preparation of flavonoid derivatives

Abstract : Different strategies for the synthesis of 2′-hydroxy-4′- methylsulfonylacetophenone are reported in the present paper. This compound is considered as a key synthon for the synthesis of new flavonoid derivatives designed as potential cyclooxygenase-2 inhibitors. The retrosynthetic approach via 3′-methylsulfonylacetophenone, which included three synthetic pathways, did not allow us to obtain the expected compound. However, a synthesis from 3-mercaptophenol led to the desired acetophenone in three steps: thiophenol methylation, Friedel-Crafts acetylation and oxidation of the sulphide to the corresponding sulfone. The desired compound, 2′-hydroxy-4′- methylsulfonylacetophenone, will be used as a synthon for the preparation of novel flavonoid derivatives, such as 2′-hydroxychalcones, flavanones, flavones, and flavonols.
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https://hal-unilim.archives-ouvertes.fr/hal-00988352
Contributeur : Vincent Sol <>
Soumis le : mercredi 7 mai 2014 - 18:04:53
Dernière modification le : mardi 20 mars 2018 - 16:36:15

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Rockhaya Gueye, Christelle Pouget, Yves Champavier, Jacques Buxeraud, Jean-Luc Duroux, et al.. synthetic strategies to 2'-hydroxy-4'-methylsulfonylacetophenone, a key compound for the preparation of flavonoid derivatives. Comptes Rendus Chimie, Elsevier Masson, 2014, pp.443-449. ⟨10.1016/j.crci.2013.10.004⟩. ⟨hal-00988352⟩

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