Direct Synthesis of 3‐Arylphthalides Promoted by Eaton's reagent

Enzo Eddebbarh (1, 2) , Léa Moutardier (2) , Jérôme Thibonnet (1) , Emilie Camiade (2) , Julien Petrignet (1)

1 SIMBA - Synthèse et isolement de molécules bio-actives
2 UMR ISP - Infectiologie et Santé Publique

A rapid method has been developed for the synthesis of 3‐arylphthalides from readily available starting materials. We describe herein a direct approach based on a simple Friedel‐Crafts condensation between an aromatic ester and an aldehyde promoted by a mixture of phosphorus pentoxide and methanesulfonic acid (Eaton's reagent) under metal and solvent‐free conditions. Due to their similarity to cytosporone E (a natural antibacterial phthalide), some of the synthesized compounds were tested as antibacterial agents against methicillin‐resistant strain of Staphylococcus aureus .

Mots clés: Friedel-Crafts; Eaton's reagent; phthalides; anti-MRSA

Domaines: Chimie

Enzo Eddebbarh, Léa Moutardier, Jérôme Thibonnet, Emilie Camiade, Julien Petrignet. Direct Synthesis of 3‐Arylphthalides Promoted by Eaton's reagent. European Journal of Organic Chemistry, 2024, 27 (8), pp.e202301303. ⟨10.1002/ejoc.202301303⟩. ⟨hal-04523497⟩