Phosphine-Initiated General-Base-Catalyzed Quinolone Synthesis.

Phosphinocatalysis provides a new approach toward 3-substituted-4-quinolones. A simple procedure, which uses Ph3P as an inexpensive catalyst and S-phenyl 2-(N-tosylamido)benzothioates and activated alkynes as starting materials, provides direct access to several 3-aroyl-4-quinolones and methyl 4-quinolone-3-carboxylate esters. The reaction presumably occurs through general base catalysis, with the initial addition of Ph3P to the activated alkyne generating the phosphonium enoate zwitterion, which acts as the strong base that initiates the reaction.