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2-氨基-1,4-萘醌作为萘醌稠合氮杂环的关键前体:合成方法与机理展望

2-Amino-1,4-naphthoquinone as a key precursor for naphthoquinone-fused N-heterocycles: synthetic approaches and mechanistic perspectives.

作者信息

Chaurasia Ujjain, Parvin Tasneem

机构信息

Department of Chemical Science and Technology, National Institute of Technology Patna, Patna, Bihar, 800005, India.

出版信息

Mol Divers. 2025 May 14. doi: 10.1007/s11030-025-11201-x.

DOI:10.1007/s11030-025-11201-x
PMID:40366551
Abstract

2-Amino-1,4-naphthoquinone has gained significant attention as a key precursor for constructing naphthoquinone-fused N-heterocycles, a class of compounds with broad applications in medicinal chemistry, materials science, and organic synthesis. Its unique structure, characterized by a reactive C-3 position and an amino group, facilitates a wide range of reactions and synthetic strategies. This review provides a comprehensive overview of recent advancements (2012-2024) in utilizing 2-amino-1,4-naphthoquinone for the development of N-heterocyclic frameworks integrating synthetic approaches with mechanistic insights. It is organized based on the type of heterocyclic rings formed, leveraging the C,N-binucleophilic properties of 2-amino-1,4-naphthoquinone.

摘要

2-氨基-1,4-萘醌作为构建萘醌稠合N-杂环的关键前体受到了广泛关注,这类化合物在药物化学、材料科学和有机合成中有着广泛的应用。其独特的结构,以活性C-3位和氨基为特征,促进了广泛的反应和合成策略。本综述全面概述了2012年至2024年期间利用2-氨基-1,4-萘醌开发N-杂环骨架的最新进展,将合成方法与机理见解相结合。它是根据形成的杂环类型进行组织的,利用了2-氨基-1,4-萘醌的C,N-双亲核性质。

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本文引用的文献

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Sci Rep. 2024 Nov 8;14(1):27302. doi: 10.1038/s41598-024-78468-2.
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-Heterocyclic Carbene-Catalyzed [3 + 3] Annulation of Enals with Aminonaphthoquinones for the Synthesis of Functionalized Aza-anthraquinones.
J Org Chem. 2024 Nov 15;89(22):16433-16443. doi: 10.1021/acs.joc.4c01655. Epub 2024 Nov 4.
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Recent research on the physicochemical properties and biological activities of quinones and their practical applications: a comprehensive review.最近关于醌类化合物的物理化学性质、生物活性及其实际应用的研究:综述。
Food Funct. 2024 Sep 16;15(18):8973-8997. doi: 10.1039/d4fo02600d.
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Multicomponent synthesis of 3-(1H-indol-3-yl)-2-phenyl-1H-benzo[f]indole-4,9-dione derivatives.3-(1H-吲哚-3-基)-2-苯基-1H-苯并[f]吲哚-4,9-二酮衍生物的多组分合成
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