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无过渡金属条件下1,5 - 二酮的一锅法合成：在2,4,6 - 三芳基吡啶衍生物合成中的应用

One-Pot Synthesis of 1,5-Diketones under a Transition-Metal-Free Condition: Application in the Synthesis of 2,4,6-Triaryl Pyridine Derivatives.

作者信息

Asressu Kesatebrhan Haile, Chan Chieh-Kai, Wang Cheng-Chung

机构信息

Institute of Chemistry, Academia Sinica, Taipei 115, Taiwan.

出版信息

ACS Omega. 2021 Mar 9;6(11):7296-7311. doi: 10.1021/acsomega.0c05328. eCollection 2021 Mar 23.

DOI:10.1021/acsomega.0c05328
PMID:33778244
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7992091/
Abstract

We developed a facile and green one-pot synthetic method for substituted 1,3,5-triaryl-1,5-diketones by Claisen-Schmidt condensation following Michael addition reaction of aryl ketones and aryl aldehydes under a transition-metal-free condition. This convenient one-pot synthetic strategy has several advantages, including being transition-metal-free, having no extra additives or reagents, having a broad substrate scope, having a high isolated yield, having a minimum amount of base employment, having a shorter reaction time, use of cheap starting materials, cost-effectiveness, and being environment friendly. Some of the chemical structures of 1,5-diketones were confirmed by X-ray single-crystal diffraction analysis. The application of 1,5-diketones was demonstrated in the preparation of 2,4,6-triaryl pyridine derivatives under a catalyst-free system using ammonium acetate as a nitrogen source.

摘要

我们开发了一种简便、绿色的一锅法合成方法，用于在无过渡金属条件下，通过芳基酮与芳基醛的迈克尔加成反应后的克莱森-施密特缩合反应制备取代的1,3,5-三芳基-1,5-二酮。这种便捷的一锅法合成策略具有多个优点，包括无过渡金属、无需额外添加剂或试剂、底物范围广、分离产率高、碱用量最少、反应时间短、使用廉价起始原料、成本效益高以及环境友好。部分1,5-二酮的化学结构通过X射线单晶衍射分析得以确认。1,5-二酮的应用在以醋酸铵作为氮源的无催化剂体系中制备2,4,6-三芳基吡啶衍生物时得到了证明。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84fe/7992091/30a40a4a29ce/ao0c05328_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84fe/7992091/b3d34c7e5c49/ao0c05328_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84fe/7992091/50988dfbe8a4/ao0c05328_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84fe/7992091/30a40a4a29ce/ao0c05328_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84fe/7992091/b3d34c7e5c49/ao0c05328_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84fe/7992091/50988dfbe8a4/ao0c05328_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84fe/7992091/30a40a4a29ce/ao0c05328_0004.jpg

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