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A one‐pot strategy for the synthesis of substituted isocoumarin, flavone, and isoquinolinedione derivatives through a switchable C‐arylation/lactonization or SNAr reaction from a wide range of soft nucleophiles and o‐quinol acetates has been developed. This base‐mediated protocol proceeds under transition‐metal‐free conditions and selectively affords various heteroarenes in 13–98% yields from readily prepared or commercially available 1,3‐dicarbonyl and α‐EWG‐substituted carbonyl compounds. The synthetic utility is further demonstrated in the synthesis of potential anti‐HIV and anti‐coronavirus derivatives and COX‐2 inhibitors. In addition, detailed experimental and computational studies are performed to provide an intensive understanding and strong support of the reaction mechanism. [ABSTRACT FROM AUTHOR]

Chemoselectivity, Regioselectivity, Quinones, Computational chemistry, Inflammation Front Cover Picture: Chemo- and Regioselective Construction of Functionalized Isocoumarin, Flavone, and Isoquinolinedione via a One-pot Reaction of o-Quinol Acetate and Soft Nucleophiles (Adv. Keywords: Chemoselectivity; Regioselectivity; Quinones; Computational chemistry; Inflammation EN Chemoselectivity Regioselectivity Quinones Computational chemistry Inflammation 2763 2763 1 09/07/23 20230905 NES 230905 The front cover picture illustrates the synthetic strategy for the regioselective installation of various soft nucleophiles at the C6 position of the highly reactive I o i -quinol acetate by 1,6-addition. [Extracted from the article]