Electroreductive Intermolecular Coupling of 4‑Quinolones with Benzophenones: Synthesis of 2‑Substituted 4‑Quinolones

• Published in: ACS omega Vol. 4; no. 22; pp. 20080 - 20093
• Main Authors: Kise, Naoki, Yoshimura, Yoshie, Manto, Tatsuhiro, Sakurai, Toshihiko
• Format: Journal Article
• Language: English
• Published: American Chemical Society 26.11.2019
• ISSN: 2470-1343; 2470-1343
• DOI: 10.1021/acsomega.9b03342

The electroreductive coupling of 1-alkoxycarbonyl-4-quinolones with benzophenones in the presence of trimethylsilyl chloride gave adducts reacted at the 2-position of 4-quinolones as trimethylsilyl ethers. The adducts were transformed to 2-(diarylhydroxymethyl)-4-quinolones. The electroreduction of 1,3-diethoxycarbonyl-4-quinolones and polyhalogenated 3-alkoxycarbonyl-1-alkyl-4-quinolones with benzophenones also gave adducts reacted at the 2-position of 4-quinolones. On the contrary, the electroreductive coupling of 1,3-diethooxycarbonyl-8-methoxy-4-quinolones occurred at the 4-position of 4-quinolones to give 4-substituted quinolines.