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钯/银共催化的分子内氧化偶联与串联[4 + 2]环加成反应：新型稠合萘醌多环杂环化合物的合成及光物理性质

Pd/Ag-Cocatalyzed Merging Intramolecular Oxidative Coupling and Cascade [4 + 2] Cycloaddition: Synthesis and Photophysical Properties of Novel Polycyclic -Heterocycles Fused Naphthoquinones.

作者信息

Dong Yu, Chen Lin, Wu Han-Qing, Xie Li, Yu Jing-Hao, Yang Fan, Wang Yu-Ting, Liu Yu-Rong, Deng Guo-Wei, Wang Zhi-Fan

机构信息

Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, College of Chemistry and Life Science, Chengdu Normal University, Chengdu 611130, China.

Chengdu Institute for Drug Control, Chengdu 610061, China.

出版信息

Molecules. 2024 Nov 28;29(23):5639. doi: 10.3390/molecules29235639.

DOI:10.3390/molecules29235639
PMID:39683797
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11643544/
Abstract

We report a step-economic strategy for the direct synthesis of novel polycyclic -heterocycle-fused naphthoquinones by merging intramolecular oxidative coupling and cascade [4 + 2] cycloaddition. In the protocol, mechanistic investigations suggest that the cascade reaction involves the intermediate spiro polycyclic -heterocycles and [4 + 2] cycloaddition processes. This protocol is featured with moderate to excellent yields, wide substrate scope, and divergent structures of products. In addition, the photophysical properties of the synthesized products were evaluated. These products exhibit interesting fluorescence properties, and surprisingly, the compounds have the ability to selectively recognize trifluoroacetic acid.

摘要

我们报道了一种通过分子内氧化偶联和串联[4+2]环加成直接合成新型多环-杂环稠合萘醌的步骤经济策略。在该方案中，机理研究表明串联反应涉及中间体螺环多环-杂环和[4+2]环加成过程。该方案具有中等到优异的产率、广泛的底物范围和多样的产物结构。此外，还评估了合成产物的光物理性质。这些产物表现出有趣的荧光性质，令人惊讶的是，这些化合物具有选择性识别三氟乙酸的能力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2126/11643544/97608335e09e/molecules-29-05639-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2126/11643544/047532b1d191/molecules-29-05639-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2126/11643544/e41e54bf3cd2/molecules-29-05639-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2126/11643544/57296dae038f/molecules-29-05639-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2126/11643544/3500b7c5e1b5/molecules-29-05639-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2126/11643544/ff757462fa14/molecules-29-05639-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2126/11643544/bd5532b15dd1/molecules-29-05639-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2126/11643544/97608335e09e/molecules-29-05639-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2126/11643544/047532b1d191/molecules-29-05639-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2126/11643544/e41e54bf3cd2/molecules-29-05639-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2126/11643544/57296dae038f/molecules-29-05639-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2126/11643544/3500b7c5e1b5/molecules-29-05639-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2126/11643544/ff757462fa14/molecules-29-05639-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2126/11643544/bd5532b15dd1/molecules-29-05639-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2126/11643544/97608335e09e/molecules-29-05639-g004.jpg

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本文引用的文献

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J Org Chem. 2024 May 3;89(9):6474-6488. doi: 10.1021/acs.joc.4c00545. Epub 2024 Apr 12.
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B(CF)-Catalyzed [4 + 2] Cyclization Strategy: Synthesis and Photophysical Properties of 5-Naphtho[2,3-]carbazole-8,13-dione Derivatives.B(CF3)3 催化的[4 + 2]环化策略：5-萘并[2,3-]咔唑-8,13-二酮衍生物的合成及光物理性质。
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Cobalt-Catalyzed Cycloamination: Synthesis and Photophysical Properties of Polycyclic -Heterocycles.
钴催化的环胺化反应：多环杂环化合物的合成与光物理性质
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