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最近通过多相催化反应实现喹喔啉-2(1H)-酮的直接 C-H 官能化的进展。

Recent Developments in Direct C-H Functionalization of Quinoxalin-2(1)-Ones via Heterogeneous Catalysis Reactions.

机构信息

Guizhou Provincial Key Laboratory of Coal Clean Utilization, School of Chemistry and Materials Engineering, Liupanshui Normal University, Liupanshui 553004, China.

出版信息

Molecules. 2023 Jun 27;28(13):5030. doi: 10.3390/molecules28135030.

DOI:10.3390/molecules28135030
PMID:37446689
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10343209/
Abstract

In recent years, Web of Science has published nearly one hundred reports per year on quinoxalin-2(1)-ones, which have attracted great interest due to their wide applications in pharmaceutical and materials fields, especially in recyclable heterogeneous catalytic reactions for direct C-H functionalisation. This review summarises for the first time the methods and reaction mechanisms of heterogeneous catalytic reactions of quinoxalin-2(1)-ones, including six major types of heterogeneous catalysts involved. The heterogeneous reactions of quinoxalin-2(1)-ones are summarised by classifying different types of catalytic materials (graphitic phase carbon nitride, MOF, COF, ion exchange resin, piezoelectric materials, and microsphere catalysis). In addition, this review discusses the future development of heterogeneous catalytic reactions of quinoxalin-2(1)-ones, including the construction of C-B/Si/P/R/X/Se bonds by heterogeneous catalytic reactions, the enrichment of heterogeneous catalysts such as metal oxides, graphene-based composites, doped metal nanoparticles, and molecular sieve-based porous materials, asymmetric synthesis, and other areas. The aim of this review is to contribute to the development of green and sustainable heterogeneous reaction methods for quinoxalin-2(1)-ones with applications in materials chemistry and pharmacology.

摘要

近年来,《科学引文索引》(Web of Science)每年都会发表近百篇关于喹喔啉-2(1)-酮的报告,由于其在药物和材料领域的广泛应用,特别是在可回收的多相催化反应中直接进行 C-H 官能化方面,喹喔啉-2(1)-酮引起了极大的兴趣。本综述首次总结了喹喔啉-2(1)-酮的多相催化反应的方法和反应机理,包括涉及的六种主要类型的多相催化剂。通过对不同类型的催化材料(石墨相氮化碳、MOF、COF、离子交换树脂、压电材料和微球催化)进行分类,总结了喹喔啉-2(1)-酮的多相反应。此外,本综述还讨论了喹喔啉-2(1)-酮的多相催化反应的未来发展,包括通过多相催化反应构建 C-B/Si/P/R/X/Se 键、金属氧化物、基于石墨烯的复合材料、掺杂金属纳米粒子和分子筛基多孔材料等多相催化剂的富集、不对称合成等领域。本综述的目的是为喹喔啉-2(1)-酮的绿色可持续多相反应方法的发展做出贡献,这些方法在材料化学和药理学中有应用。

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本文引用的文献

1
Direct Alkylation of Quinoxalinones with Boracene-Based Alkylborate under Visible Light Irradiation.硼烯基烷基硼酸盐在可见光照射下直接对喹喔啉酮的烷基化反应。
J Org Chem. 2023 May 5;88(9):6218-6226. doi: 10.1021/acs.joc.3c00266. Epub 2023 Apr 12.
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Metal Oxide-Supported Metal Catalysts for Electrocatalytic Oxygen Reduction Reaction: Characterization Methods, Modulation Strategies, and Recent Progress.金属氧化物负载金属催化剂用于电催化氧气还原反应:表征方法、调制策略及最新进展。
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Recent Developments in Direct C-H Functionalization of Quinoxalin-2(1)-Ones via Multi-Component Tandem Reactions.
喹喔啉-2(1H)-酮的 C-H 直接官能团化的最新进展:多组分串联反应。
Molecules. 2023 Mar 9;28(6):2513. doi: 10.3390/molecules28062513.
4
Radical Fluorosulfonyl Heteroarylation of Unactivated Alkenes with Quinoxalin-2(1)-ones and Related N-Heterocycles.未活化烯烃与喹喔啉-2(1)-酮及相关氮杂环的自由基氟磺酰基杂芳基化反应
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Selectfluor-Mediated Regioselective C-3 Alkoxylation, Amination, Sulfenylation, and Selenylation of Quinoxalin-2(1)-ones.氟代 Selectfluor 促进的喹喔啉-2(1H)-酮的 C-3 区域选择性烷氧基化、氨基化、硫代化和硒代化反应。
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Acid-Promoted Direct C-H Carbamoylation at the C-3 Position of Quinoxalin-2(1)-ones with Isocyanide in Water.水相中酸促进喹喔啉-2(1)-酮C-3位与异腈的直接C-H氨基甲酰化反应
ACS Omega. 2022 Dec 16;8(1):1577-1587. doi: 10.1021/acsomega.2c06946. eCollection 2023 Jan 10.
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Sunlight Induced and Recyclable g-CN Catalyzed C-H Sulfenylation of Quinoxalin-2(1)-Ones.阳光诱导和可回收 g-CN 催化的喹喔啉-2(1H)-酮的 C-H 硫代化反应。
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