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  1. 学術雑誌論文

Chemistry of Nitroquinolones and Synthetic Application to Unnatural 1-Methyl-2-quinolone Derivatives

http://hdl.handle.net/10173/1359
http://hdl.handle.net/10173/1359
bc45d9ef-cf8b-46c3-a747-4148380fbe90
名前 / ファイル ライセンス アクション
27-11.pdf 27-11.pdf (1.8 MB)
Item type 学術雑誌論文 / Journal Article(1)
公開日 2016-03-25
タイトル
タイトル Chemistry of Nitroquinolones and Synthetic Application to Unnatural 1-Methyl-2-quinolone Derivatives
言語
言語 eng
資源タイプ
資源タイプ識別子 http://purl.org/coar/resource_type/c_6501
資源タイプ journal article
著者 Nishiwaki, Nagatoshi

× Nishiwaki, Nagatoshi

Nishiwaki, Nagatoshi

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内容記述タイプ Abstract
内容記述 The 1-methyl-2-quinolone (MeQone) framework is often found in alkaloids and recently attention was drawn to unnatural MeQone derivatives with the aim of finding new biologically active compounds, however, low reactivity of the MeQone framework prevents the syntheses of versatile derivatives. A nitro group is one of the useful activating groups for this framework that enables a concise chemical transformation. Among nitroquinolones, 1-methyl-3,6,8-trinitro-2-quinolone (TNQ) exhibits unusual reactivity favoring region-selective cine-substitutions that afford 4-substituted 1-methyl-6,8-dinitro-2-quinolones upon treatment with nucleophilic reagents. Contrary to this, 1-methyl-3,6-dinitro-2-quinolone (3,6-DNQ) does not undergo any reaction under the same conditions. The unusual reactivity of TNQ is caused by steric repulsion between the methyl group at the 1-position and the nitro group at the 8-position, which distorts the MeQone framework. As a result, the pyridone ring of TNQ loses aromaticity and acts rather as an activated nitroalkene. Indeed, the pyridone moiety of TNQ undergoes cycloaddition with electron-rich alkenes or dienes under mild conditions, whereby a new fused ring is constructed on the [c]-face of the MeQone. Consequently, TNQ can be used as a new scaffold leading to versatile unnatural MeQone derivatives.
書誌情報 Molecules

巻 15, 号 8, p. 5174-5195, 発行日 2010
ISSN
収録物識別子タイプ ISSN
収録物識別子 1420-3049
DOI
関連タイプ isIdenticalTo
識別子タイプ DOI
関連識別子 10.3390/molecules15085174
権利
権利情報 This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
権利(URI)
権利情報 http://creativecommons.org/licenses/by/3.0/ | http://creativecommons.org/licenses/by/3.0/
著者版フラグ
出版タイプ VoR
出版タイプResource http://purl.org/coar/version/c_970fb48d4fbd8a85
出版者
出版者 MDPIAG
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