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二茂铁基共轭恶唑并氮杂卓/喹啉：多炔偶联及扩环或重排

Ferrocenyl conjugated oxazepines/quinolines: multiyne coupling and ring-expanding or rearrangement.

作者信息

Lei Yu, Bao Li, Hu Qiong, Zhang Ke, Zong Lingli, Hu Yimin

机构信息

College of Chemistry and Materials Science, Anhui Normal University, Wuhu, China.

出版信息

Front Chem. 2024 Jul 31;12:1441539. doi: 10.3389/fchem.2024.1441539. eCollection 2024.

DOI:10.3389/fchem.2024.1441539
PMID:39144699
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11322062/
Abstract

Ferrocenyl conjugated oxazepine/quinoline derivatives were presented through the reaction of hexadehydro-Diels-Alder (HDDA) generated arynes with ferrocenyl oxazolines under mild conditions ring-expanding or rearrangement processes. Water molecule participated in this unexpected rearrangement process to produce quinoline skeletons, and DFT calculations supported a ring-expanding and intramolecular hydrogen migration process for the formation of oxazepine derivatives. Two variants of this chemistry, expanded the reactivity between ferrocenyl conjugated substances and arynes, further providing an innovative approach for the synthesis of ferrocene derivatives.

摘要

通过在温和条件下六脱氢狄尔斯-阿尔德（HDDA）生成的芳炔与二茂铁基恶唑啉的反应，呈现出二茂铁基共轭恶唑嗪/喹啉衍生物，该反应涉及扩环或重排过程。水分子参与了这一意外的重排过程以生成喹啉骨架，密度泛函理论（DFT）计算支持了形成恶唑嗪衍生物的扩环和分子内氢迁移过程。这种化学反应的两个变体扩展了二茂铁基共轭物质与芳炔之间的反应活性，进一步为二茂铁衍生物的合成提供了一种创新方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e8e/11322062/621201556cf2/fchem-12-1441539-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e8e/11322062/5bac030bcf43/fchem-12-1441539-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e8e/11322062/695b35c9d6da/FCHEM_fchem-2024-1441539_wc_sch1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e8e/11322062/8481db916fed/FCHEM_fchem-2024-1441539_wc_sch2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e8e/11322062/b212a1833ecd/FCHEM_fchem-2024-1441539_wc_sch3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e8e/11322062/ea08173fb045/fchem-12-1441539-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e8e/11322062/69f5a17cf428/fchem-12-1441539-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e8e/11322062/621201556cf2/fchem-12-1441539-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e8e/11322062/5bac030bcf43/fchem-12-1441539-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e8e/11322062/695b35c9d6da/FCHEM_fchem-2024-1441539_wc_sch1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e8e/11322062/8481db916fed/FCHEM_fchem-2024-1441539_wc_sch2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e8e/11322062/b212a1833ecd/FCHEM_fchem-2024-1441539_wc_sch3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e8e/11322062/ea08173fb045/fchem-12-1441539-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e8e/11322062/69f5a17cf428/fchem-12-1441539-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e8e/11322062/621201556cf2/fchem-12-1441539-g004.jpg

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本文引用的文献

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Nat Commun. 2024 Apr 30;15(1):3665. doi: 10.1038/s41467-024-47952-8.
2
Access to Fully Substituted Dihydroindazoles Via Hexadehydro-Diels-Alder/[3 + 2] Cycloaddition.通过十六碳二烯-[3 + 2]环加成反应获得完全取代的二氢吲哚。
J Org Chem. 2023 Oct 20;88(20):14736-14747. doi: 10.1021/acs.joc.3c01901. Epub 2023 Oct 11.
3
Regioselective Synthesis of Directly Connected BODIPY Dimers through Oxidative Coupling of α-Amino-Substituted BODIPYs.
通过α-氨基取代 BODIPY 的氧化偶联反应，区域选择性合成直接连接的 BODIPY 二聚体。
Org Lett. 2023 Jul 14;25(27):5055-5060. doi: 10.1021/acs.orglett.3c01755. Epub 2023 Jul 2.
4
Merging enzymes with chemocatalysis for amide bond synthesis.将酶与化学催化相结合用于酰胺键合成。
Nat Commun. 2022 Jan 19;13(1):380. doi: 10.1038/s41467-022-28005-4.
5
Has Ferrocene Really Delivered Its Role in Accentuating the Bioactivity of Organic Scaffolds?二茂铁是否真的在增强有机支架的生物活性方面发挥了作用？
J Med Chem. 2021 Dec 9;64(23):16865-16921. doi: 10.1021/acs.jmedchem.1c00390. Epub 2021 Nov 18.
6
Fully Substituted Conjugate Benzofuran Core: Multiyne Cascade Coupling and Oxidation of Cyclopropenone.全取代共轭苯并呋喃核心：多炔串联偶联与环丙烯酮的氧化
Org Lett. 2021 Jul 2;23(13):4971-4975. doi: 10.1021/acs.orglett.1c01304. Epub 2021 Jun 11.
7
The Redox Journey of Iconic Ferrocene: Ferrocenium Dications and Ferrocenate Anions.标志性二茂铁的氧化还原历程：二茂铁鎓二价阳离子与二茂铁酸根阴离子
Angew Chem Int Ed Engl. 2021 Jun 1;60(23):12632-12635. doi: 10.1002/anie.202101770. Epub 2021 Apr 29.
8
Reactions of HDDA Benzynes with -Diarylimines (ArCH=NAr').HDDA苯炔与二芳基亚胺（ArCH=NAr'）的反应
European J Org Chem. 2020 May 3;2020(16):2379-2383. doi: 10.1002/ejoc.201901855. Epub 2020 Feb 13.
9
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Org Lett. 2021 Apr 2;23(7):2676-2681. doi: 10.1021/acs.orglett.1c00581. Epub 2021 Mar 15.
10
-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors.硅芳基三氟甲磺酸酯：小林芳炔前体的探索之旅。
Chem Rev. 2021 Apr 14;121(7):3892-4044. doi: 10.1021/acs.chemrev.0c01011. Epub 2021 Feb 18.