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

ABSTRACT: 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.

SUBMITTER: Kise N

PROVIDER: S-EPMC6882170 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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

Kise Naoki N Yoshimura Yoshie Y Manto Tatsuhiro T Sakurai Toshihiko T

ACS omega 20191115 22

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 electro ...[more]

PMID: 31788643

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