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4-喹诺酮与二苯甲酮的电还原分子间偶联：2-取代4-喹诺酮的合成

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

作者信息

Kise Naoki, Yoshimura Yoshie, Manto Tatsuhiro, Sakurai Toshihiko

机构信息

Department of Chemistry and Biotechnology, Graduate School of Engineering and Center for Research on Green Sustainable Chemistry, Graduate School of Engineering, Tottori University, 4-101 Koyama-cho Minami, Tottori 680-8552, Japan.

出版信息

ACS Omega. 2019 Nov 15;4(22):20080-20093. doi: 10.1021/acsomega.9b03342. eCollection 2019 Nov 26.

DOI:10.1021/acsomega.9b03342
PMID:31788643
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6882170/
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.

摘要

在三甲基氯硅烷存在下，1-烷氧羰基-4-喹诺酮与二苯甲酮的电还原偶联反应生成了在4-喹诺酮2-位以三甲基硅醚形式反应的加合物。这些加合物可转化为2-(二芳基羟甲基)-4-喹诺酮。1,3-二乙氧羰基-4-喹诺酮和多卤代3-烷氧羰基-1-烷基-4-喹诺酮与二苯甲酮的电还原反应同样生成了在4-喹诺酮2-位反应的加合物。相反，1,3-二乙氧羰基-8-甲氧基-4-喹诺酮的电还原偶联反应发生在4-喹诺酮的4-位，生成4-取代喹啉。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b79d/6882170/6a568a6f1592/ao9b03342_0017.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b79d/6882170/22a2d0f989b6/ao9b03342_0015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b79d/6882170/fc5352e93ab9/ao9b03342_0013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b79d/6882170/47cdacacaf19/ao9b03342_0016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b79d/6882170/7bb757e83568/ao9b03342_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b79d/6882170/5e3340c8e50f/ao9b03342_0006.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b79d/6882170/6a568a6f1592/ao9b03342_0017.jpg

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