ABSTRACT
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. © 2023 Wiley-VCH GmbH.