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构建2-氨基吩恶嗪酮结构的新合成方法。

New synthetic approaches for the construction of 2-aminophenoxazinone architectures.

作者信息

Guo Ning-Yu, Cheng Xiao-Yi, Dong Xiao-Dan, Peng Chun-E, Zhang Chun, Han Ya-Ping, Peng Li-Zeng

机构信息

School of Chemical Engineering and Technology, Hebei University of Technology Tianjin 300130 China

Key Laboratory of Agro-Products Processing Technology of Shandong Province, Key Laboratory of Novel Food Resources Processing, Ministry of Agriculture, Institute of Agro-Food Science and Technology, Shandong Academy of Agricultural Sciences Jinan China.

出版信息

RSC Adv. 2025 Mar 28;15(12):9479-9509. doi: 10.1039/d5ra00604j. eCollection 2025 Mar 21.

DOI:10.1039/d5ra00604j
PMID:40161528
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11951111/
Abstract

Elaborated molecular architectures, specifically those containing a 2-aminophenoxazinone scaffold, belong to one of the most ubiquitous and prominent classes of heterocyclic frameworks, going from natural products to biologically active pharmaceutical molecules and from agrochemicals to functional materials and polymers. Therefore, efficient synthetic strategies for the assembly of 2-aminophenoxazinone frameworks are always in demand and have gained attention in academic and industrial communities. Methodologies that involve cascade reactions generally catalyzed by transition metal complexes, such as iron, cobalt, manganese, copper, and zinc complexes, have stood out as a representative approach. Over the past few decades, a great deal of versatile, atom-economic, and straightforward protocols have been reported for the generation of value-added 2-aminophenoxazinone frameworks in a sustainable, powerful, and applicable manner. The state-of-the-art methodologies toward the construction of 2-aminophenoxazinone skeletons are summarized in this review, which could be divided into four categories: (1) construction of 2-aminophenoxazinone compounds catalyzed by transition metal complexes; (2) construction of 2-aminophenoxazinone compounds catalyzed by biosynthetic enzymes; (3) synthetic process routes of 2-aminophenoxazinone compounds; and (4) construction of 2-aminophenoxazinone compounds other innovative methods.

摘要

精心设计的分子结构,特别是那些含有2-氨基吩恶嗪酮骨架的结构,属于最普遍且突出的杂环骨架类别之一,涵盖了从天然产物到生物活性药物分子,从农用化学品到功能材料和聚合物等领域。因此,用于组装2-氨基吩恶嗪酮骨架的高效合成策略一直备受需求,并在学术界和工业界受到关注。涉及通常由过渡金属配合物(如铁配合物、钴配合物、锰配合物、铜配合物和锌配合物)催化的级联反应的方法,已成为一种具有代表性的方法。在过去几十年中,已经报道了大量通用、原子经济且直接的方案,用于以可持续、强大且适用的方式生成有附加值的2-氨基吩恶嗪酮骨架。本综述总结了构建2-氨基吩恶嗪酮骨架的最新方法,可分为四类:(1)过渡金属配合物催化构建2-氨基吩恶嗪酮化合物;(2)生物合成酶催化构建2-氨基吩恶嗪酮化合物;(3)2-氨基吩恶嗪酮化合物的合成工艺路线;(4)构建2-氨基吩恶嗪酮化合物的其他创新方法。

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J Agric Food Chem. 2022 Jun 29;70(25):7742-7750. doi: 10.1021/acs.jafc.2c03216. Epub 2022 Jun 15.
5
Exploring Anticancer and (Bio)catalytic Activities of New Oxovanadium(V), Dioxomolybdenum(VI), and Copper(II) Complexes of Amide-Imine Conjugates.探索新型酰胺-亚胺共轭物的氧钒(V)、二氧钼(VI)和铜(II)配合物的抗癌及(生物)催化活性
ACS Appl Bio Mater. 2019 Jul 15;2(7):2802-2811. doi: 10.1021/acsabm.9b00226. Epub 2019 Jun 20.
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Design, synthesis, structural, spectral, and redox properties and phenoxazinone synthase activity of tripodal pentacoordinate Mn(II) complexes with impressive turnover numbers.具有令人印象深刻的周转率的三脚架五配位 Mn(II)配合物的设计、合成、结构、光谱和氧化还原性质以及苯并噁嗪酮合酶活性。
Dalton Trans. 2021 Nov 23;50(45):16601-16612. doi: 10.1039/d1dt01925b.
7
Visible-Light-Mediated Synthesis of Substituted Phenazine and Phenoxazinone Using Eosin Y as a Photoredox Catalyst.以曙红Y为光氧化还原催化剂的可见光介导取代吩嗪和吩恶嗪酮的合成
Org Lett. 2021 May 7;23(9):3269-3273. doi: 10.1021/acs.orglett.1c00725. Epub 2021 Apr 21.
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Joining of Trinuclear Heterometallic Cu-M (M = Mn, Cd) Nodes by Nicotinate to Form 1D Chains: Magnetic Properties and Catalytic Activities.三核异金属 Cu-M(M=Mn,Cd)节点通过烟酸盐连接形成 1D 链:磁性和催化活性。
Inorg Chem. 2020 Oct 19;59(20):14989-15003. doi: 10.1021/acs.inorgchem.0c01733. Epub 2020 Oct 1.
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Modulation of Nuclearity in Cu -Mn Complexes of a N O Donor Ligand Depending upon Carboxylate Anions: Structures, Magnetic Properties and Catalytic Oxidase Activities.基于羧酸根阴离子的一氧化氮供体配体的铜 - 锰配合物中核数的调制:结构、磁性及催化氧化酶活性
Chem Asian J. 2020 Dec 1;15(23):4055-4069. doi: 10.1002/asia.202000706. Epub 2020 Oct 28.
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Phenoxazinone synthase-like catalytic activity of novel mono- and tetranuclear copper(ii) complexes with 2-benzylaminoethanol.具有 2-苄氨基乙醇的新型单核和四核铜(II)配合物的苯并恶嗪酮合酶样催化活性。
Dalton Trans. 2020 Apr 15;49(15):4710-4724. doi: 10.1039/d0dt00222d.