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吡喃并双香豆素的三组分合成：通往吡啶酮和吡喃酮并香豆素的途径。

Three-component synthesis of pyran-fused biscoumarins: an entry to pyridinone- and pyranone-fused coumarins.

作者信息

Lee Jui-Ting, Jatangi Nagesh, Vyasamudri Sameer, Yang Ding-Yah

机构信息

Graduate Program for Biomedical and Materials Science, Tunghai University Taiwan

Department of Chemistry, Tunghai University No. 1727, Sec. 4, Taiwan Boulevard, Xitun District Taichung 407224 Taiwan.

出版信息

RSC Adv. 2024 May 7;14(21):14767-14774. doi: 10.1039/d4ra01681e. eCollection 2024 May 2.

DOI:10.1039/d4ra01681e
PMID:38716092
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11075138/
Abstract

A base-mediated, three-component synthesis of symmetric and unsymmetric pyran-fused biscoumarins the coupling of 4-hydroxycoumarin with 4-chloro-3-formylcoumarin in ethanol is reported. This methodology is further extended to the construction of various indole/coumarin-substituted symmetric pyran-fused biscoumarins. The unsymmetric pyran-fused biscoumarin can react with amines and 4-hydroxycoumarins under basic and acidic conditions to afford pyridinone-fused coumarins and pyranone-fused coumarins, respectively. The mechanisms of their formation are proposed.

摘要

报道了一种碱介导的对称和不对称吡喃并双香豆素的三组分合成方法，即4-羟基香豆素与4-氯-3-甲酰基香豆素在乙醇中的偶联反应。该方法进一步扩展到构建各种吲哚/香豆素取代的对称吡喃并双香豆素。不对称吡喃并双香豆素在碱性和酸性条件下分别与胺和4-羟基香豆素反应，得到吡啶酮并香豆素和吡喃酮并香豆素。并提出了它们的形成机理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d00/11075138/947979fb6a3f/d4ra01681e-s9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d00/11075138/8bda1b27af7b/d4ra01681e-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d00/11075138/f9c80f76e728/d4ra01681e-s8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d00/11075138/947979fb6a3f/d4ra01681e-s9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d00/11075138/8bda1b27af7b/d4ra01681e-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d00/11075138/f9c80f76e728/d4ra01681e-s8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d00/11075138/947979fb6a3f/d4ra01681e-s9.jpg

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本文引用的文献

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Chem Sci. 2023 Oct 16;14(42):11850-11857. doi: 10.1039/d3sc03452f. eCollection 2023 Nov 1.
2
Design and synthesis of hybrid compounds as novel drugs and medicines.作为新型药物的杂化化合物的设计与合成。
RSC Adv. 2022 Jul 6;12(30):19470-19484. doi: 10.1039/d2ra03281c. eCollection 2022 Jun 29.
3
Hybrid Drugs-A Strategy for Overcoming Anticancer Drug Resistance?
杂交药物——克服抗癌药物耐药性的一种策略？
Molecules. 2021 Apr 29;26(9):2601. doi: 10.3390/molecules26092601.
4
Brønsted Acid-Catalyzed Formal (3+3)-Annulation of Propargylic (Aza)--Quinone Methides with 4-Hydroxycoumarins and 1,3-Dicarbonyl Compounds.布朗斯特酸催化的炔丙基（氮杂）-醌甲醚与 4-羟基香豆素和 1,3-二羰基化合物的形式（3+3）环化反应。
J Org Chem. 2021 May 7;86(9):6075-6089. doi: 10.1021/acs.joc.0c02844. Epub 2021 Apr 6.
5
Regiodivergent Synthesis of Bis(4-oxycoumarin)-based Dioxabicycles: Exploration of [4 + 4] (Heterocyclo)reversion/addition and 1,5-Hydrogen Shift Photochromism.基于双（4-氧代香豆素）的二氧杂双环的区域发散合成：[4 + 4]（杂环）反转/加成和1,5-氢迁移光致变色的探索
Org Lett. 2020 Apr 17;22(8):3166-3170. doi: 10.1021/acs.orglett.0c00904. Epub 2020 Apr 7.
6
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Org Lett. 2019 Jul 5;21(13):5225-5228. doi: 10.1021/acs.orglett.9b01830. Epub 2019 Jun 24.
7
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J Org Chem. 2017 Dec 15;82(24):13594-13601. doi: 10.1021/acs.joc.7b01902. Epub 2017 Nov 27.
8
Hybrid molecules: The privileged scaffolds for various pharmaceuticals.杂化分子：各种药物的优势骨架。
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9
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Org Lett. 2013 Jun 7;15(11):2802-5. doi: 10.1021/ol401138q. Epub 2013 May 28.