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

Rockhaya Gueye (1) , Christelle Pouget (1) , Yves Champavier (2) , Jacques Buxeraud (1) , Jean-Luc Duroux (1) , Catherine Fagnère (1)

1 LCSN - Laboratoire de Chimie des Substances Naturelles
2 RMN - Service Commun de Résonance Magnétique Nucléaire

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.

Mots clés: Ketones; Synthetic methods; Acylation; Electrophilic substitution; Lewis acids

Domaines: Chimie organique

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, 2014, 17, pp.443-449. ⟨10.1016/j.crci.2013.10.004⟩. ⟨hal-00988352⟩