SCHEDULED MAINTENANCE
Pd-Catalyzed sequential β-C(sp3)–H arylation and intramolecular amination of δ-C(sp2)–H bonds for synthesis of quinolinones via an N,O-bidentate directing group†
Abstract
The pharmacological importance of 2-quinolinone derivatives is well known. Herein, we developed an effective protocol for the synthesis of 2-quinolinone derivatives by palladium-catalyzed sequential β-C(sp3)–H arylation and selective intramolecular C(sp2)–H/N–H amination starting with aryl iodides and carboxylic acids. A novel directing group, glycine dimethylamide, was used in the synthesis. We synthesized various quinolinone derivatives, including 5-substituted quinolinones, which are difficult to obtain using the traditional pathway. The directing group could be easily removed and could be readily transformed into other useful functional groups.
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