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醌亚胺多米诺环化反应的最新进展

Recent Advances in the Domino Annulation Reaction of Quinone Imines.

作者信息

Wang Zhen-Hua, Fu Xiao-Hui, Li Qun, You Yong, Yang Lei, Zhao Jian-Qiang, Zhang Yan-Ping, Yuan Wei-Cheng

机构信息

Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu 610106, China.

School of Materials and Environmental Engineering, Chengdu Technological University, Chengdu 611730, China.

出版信息

Molecules. 2024 May 24;29(11):2481. doi: 10.3390/molecules29112481.

DOI:10.3390/molecules29112481
PMID:38893357
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11173866/
Abstract

Quinone imines are important derivatives of quinones with a wide range of applications in organic synthesis and the pharmaceutical industry. The attack of nucleophilic reagents on quinone imines tends to lead to aromatization of the quinone skeleton, resulting in both the high reactivity and the unique reactivity of quinone imines. The extreme value of quinone imines in the construction of nitrogen- or oxygen-containing heterocycles has attracted widespread attention, and remarkable advances have been reported recently. This review provides an overview of the application of quinone imines in the synthesis of cyclic compounds via the domino annulation reaction.

摘要

醌亚胺是醌的重要衍生物,在有机合成和制药工业中有广泛应用。亲核试剂对醌亚胺的进攻往往会导致醌骨架的芳构化,从而使醌亚胺具有高反应活性和独特的反应活性。醌亚胺在含氮或含氧杂环构建中的独特价值引起了广泛关注,最近已有显著进展报道。本文综述了醌亚胺通过多米诺环化反应在环状化合物合成中的应用。

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Chem Rev. 2023 Dec 13;123(23):13693-13712. doi: 10.1021/acs.chemrev.3c00479. Epub 2023 Nov 17.
3
-Clavilactone J and Its Quinone Derivative, Meroterpenoids from the Fungus sp.
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J Nat Prod. 2023 Nov 24;86(11):2580-2584. doi: 10.1021/acs.jnatprod.3c00174. Epub 2023 Nov 6.
4
Diversity-Oriented Catalytic Asymmetric Dearomatization of Indoles with o-Quinone Diimides.邻醌二亚胺导向的吲哚的多样性导向催化不对称去芳构化反应
Adv Sci (Weinh). 2023 Dec;10(35):e2305101. doi: 10.1002/advs.202305101. Epub 2023 Oct 23.
5
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6
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