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

[Image: see text] 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 el...

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Autores principales: Kise, Naoki, Yoshimura, Yoshie, Manto, Tatsuhiro, Sakurai, Toshihiko
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6882170/
https://www.ncbi.nlm.nih.gov/pubmed/31788643
http://dx.doi.org/10.1021/acsomega.9b03342
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author Kise, Naoki
Yoshimura, Yoshie
Manto, Tatsuhiro
Sakurai, Toshihiko
author_facet Kise, Naoki
Yoshimura, Yoshie
Manto, Tatsuhiro
Sakurai, Toshihiko
author_sort Kise, Naoki
collection PubMed
description [Image: see text] 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.
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spelling pubmed-68821702019-11-29 Electroreductive Intermolecular Coupling of 4-Quinolones with Benzophenones: Synthesis of 2-Substituted 4-Quinolones Kise, Naoki Yoshimura, Yoshie Manto, Tatsuhiro Sakurai, Toshihiko ACS Omega [Image: see text] 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. American Chemical Society 2019-11-15 /pmc/articles/PMC6882170/ /pubmed/31788643 http://dx.doi.org/10.1021/acsomega.9b03342 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Kise, Naoki
Yoshimura, Yoshie
Manto, Tatsuhiro
Sakurai, Toshihiko
Electroreductive Intermolecular Coupling of 4-Quinolones with Benzophenones: Synthesis of 2-Substituted 4-Quinolones
title Electroreductive Intermolecular Coupling of 4-Quinolones with Benzophenones: Synthesis of 2-Substituted 4-Quinolones
title_full Electroreductive Intermolecular Coupling of 4-Quinolones with Benzophenones: Synthesis of 2-Substituted 4-Quinolones
title_fullStr Electroreductive Intermolecular Coupling of 4-Quinolones with Benzophenones: Synthesis of 2-Substituted 4-Quinolones
title_full_unstemmed Electroreductive Intermolecular Coupling of 4-Quinolones with Benzophenones: Synthesis of 2-Substituted 4-Quinolones
title_short Electroreductive Intermolecular Coupling of 4-Quinolones with Benzophenones: Synthesis of 2-Substituted 4-Quinolones
title_sort electroreductive intermolecular coupling of 4-quinolones with benzophenones: synthesis of 2-substituted 4-quinolones
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6882170/
https://www.ncbi.nlm.nih.gov/pubmed/31788643
http://dx.doi.org/10.1021/acsomega.9b03342
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AT yoshimurayoshie electroreductiveintermolecularcouplingof4quinoloneswithbenzophenonessynthesisof2substituted4quinolones
AT mantotatsuhiro electroreductiveintermolecularcouplingof4quinoloneswithbenzophenonessynthesisof2substituted4quinolones
AT sakuraitoshihiko electroreductiveintermolecularcouplingof4quinoloneswithbenzophenonessynthesisof2substituted4quinolones

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