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由β-酮酰胺高效且多样化地合成多官能化2-吡啶酮。

Efficient and divergent synthesis of polyfunctionalized 2-pyridones from β-keto amides.

作者信息

Gao Baochang, Sun Yufeng, Wang Jun, Yuan Zhigang, Zu Liwu, Zhang Xu, Liu Wenbin

机构信息

Institute of Composite Materials, Key Laboratory of Superlight Material and Surface Technology of Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University Harbin 150001 P. R. China

Daqing Branch of Heilongjiang Academy of Sciences Daqing 163319 P. R. China.

出版信息

RSC Adv. 2018 Oct 1;8(59):33625-33630. doi: 10.1039/c8ra05709e. eCollection 2018 Sep 28.

DOI:10.1039/c8ra05709e
PMID:35548816
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9086556/
Abstract

Efficient and divergent one-pot synthesis of polyfunctionalized 2-pyridones from β-keto amides based on reaction condition selection was developed. The methodology offers several significant advantages including mild conditions, ease of handling, high yields, and a relatively broad range of substrates. Based on various experiments and observations, a plausible mechanism for the selective synthesis of 2-pyridones was proposed.

摘要

基于反应条件的选择，开发了一种从β-酮酰胺高效、多样的一锅法合成多官能化2-吡啶酮的方法。该方法具有几个显著优点，包括反应条件温和、易于操作、产率高以及底物范围相对较广。基于各种实验和观察结果，提出了一种选择性合成2-吡啶酮的合理机制。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3de5/9086556/d236a136cc88/c8ra05709e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3de5/9086556/6c56361eb013/c8ra05709e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3de5/9086556/d236a136cc88/c8ra05709e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3de5/9086556/6c56361eb013/c8ra05709e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3de5/9086556/d236a136cc88/c8ra05709e-s2.jpg

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本文引用的文献

1
Divergent synthesis of dual 1,4-dihydropyridines with different substituted patterns from enaminones and aldehydes through domino reactions.通过多米诺反应从烯胺酮和醛出发，以不同取代模式发散合成双1,4 - 二氢吡啶。
RSC Adv. 2018 Apr 3;8(23):12635-12640. doi: 10.1039/c8ra01236a.
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A lesson for site-selective C-H functionalization on 2-pyridones: radical, organometallic, directing group and steric controls.2-吡啶酮上的位点选择性C-H官能化的经验教训：自由基、有机金属、导向基团和空间控制
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基于贫电子叔烯胺中组合键转化的多米诺反应。
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Structure activity relationships of 4-hydroxy-2-pyridones: A novel class of antituberculosis agents.4-羟基-2-吡啶酮的构效关系：一类新型抗结核药物。
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Antimalarial 4(1H)-pyridones bind to the Qi site of cytochrome bc1.抗疟4(1H)-吡啶酮与细胞色素bc1的Qi位点结合。
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An efficient method for the construction of polysubstituted 4-pyridones via self-condensation of β-keto amides mediated by P2O5 and catalyzed by zinc bromide.一种通过 P2O5 介导、溴化锌催化的β-酮酰胺自缩合构建多取代 4-吡啶酮的有效方法。
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Design and synthesis of novel 2'-hydroxy group substituted 2-pyridone derivatives as anticancer agents.设计并合成新型 2'-羟基取代 2-吡啶酮衍生物作为抗癌药物。
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