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喹喔啉酮及其衍生物是一类重要的含氮杂环化合物,这种特殊的杂环骨架广泛存在于各种天然产物、药物分子以及功能材料中.近年来,喹喔啉酮的官能团化引起了化学工作者的广泛关注,其中通过C—H官能团化构建3-官能团化的喹喔啉酮取得了重要进展.光氧化还原催化可利用绿色清洁的光能在较为温和的条件下实现有机化合物的合成与转化,因此,越来越多的光催化体系被开发用于喹喔啉酮的官能团化.简单高效的无过渡金属或无光催化剂的反应体系非常符合绿色化学和可持续发展的要求,已成为喹喔啉酮类化合物官能团化强有力的工具,同时也受到了很多学者的青睐.对近五年来无过渡金属或无光催化剂可见光促进喹喔啉酮的C(3)位官能团化领域所取得的研究进展进行了综述,对反应机理和氧化还原淬灭过程进行了总结,并对该领域所面临的挑战和机遇进行了展望和探讨. 相似文献
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《催化学报》2020,(8)
杂环化合物和醇的C(sp~2)-H/O-H交叉脱氢偶联反应为制备杂环醚类化合物提供了一种原子和步骤经济性的方法.然而,已经报道的交叉脱氢偶联反应大部分需要使用过渡金属催化剂和/或者强氧化剂,不仅产生环境问题还增加分离成本.同时,这些合成方法还存在杂环化合物和醇的C(sp~2)-H/C(sp~3)-H交叉脱氢偶联反应的竞争反应,降低了反应的选择性和收率.喹喔啉-2(1H)-酮是生物活性物质和人工药物的核心骨架结构之一,合成多样性官能化的喹喔啉-2(1H)-酮备受关注.近期多种C-3官能化喹喔啉-2(1H)-酮的合成方法被报道,但是目前没有一例通过无金属无强氧化剂条件下的喹喔啉-2(1H)-酮与醇C(sp~2)-H/O-H交叉脱氢偶联反应合成3-烷氧基喹喔啉-2(1H)-酮的相关工作报道.值得一提的是,利用氧气作为氧化剂的可见光催化反应符合绿色化学的要求,在最近几年中发展迅速.本文报道了一种通过可见光催化的喹喔啉-2(1H)-酮与醇的C(sp~2)-H/O-H交叉脱氢偶联反应合成3-烷氧基喹喔啉-2(1H)-酮化合物的绿色制备方法.首先通过对光催化剂、溶剂等参数的筛选,确定了最佳反应条件为喹喔啉-2(1H)-酮化合物0.3 mmol,醇0.9 mmol,乙腈1.5 m L, Acr~+-Mes Cl O_4~-2mol%,空气作为氧化剂, 3 W蓝光作为光源.在最佳条件下,含有供电子、吸电子取代基的喹喔啉-2(1H)-酮化合物和含有各种取代基的烷基醇都能很好地进行反应,得到36种目标化合物,产率70%~94%.另外,成功完成了克级放大实验和一锅法串联反应.机理研究证明,该反应是喹喔啉-2(1H)-酮化合物在光催化氧化作用下生成自由基正离子,醇作为亲核试剂选择性进攻自由基正离子的C3位,最后得到目标产物. 相似文献
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建立了一种简单、实用的光诱导一锅法高选择性N-甲基喹喔啉酮类化合物和苯乙酮类化合物合成一系列3-烷基化喹唑啉-2(1H)-酮类化合物的方法。该方法在室温条件下,以玫瑰红作为光催化剂,在18 W 460nm的蓝色LED下照射8 h,通过直接C3-H活化的方案,较好收率获得一系列相应的3-烷基化喹喔啉-2(1H)-酮类化合物,最高产率可达到76%。反应体系具有经济实用性和底物适用范围广的特点,为3-烷基化喹喔啉-2(1H)-酮类化合物类化合物的合成提供了一种简便经济的方法。 相似文献
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报道了2(1H)-喹喔啉类衍生物——1-苯基-3-甲基-6-N,N-二正丁基胺-2(1H)-喹喔啉-2-酮的全合成.该化合物及其中间体1-苯基-3-甲基-6-胺基-2(1H)-喹喔啉-2-酮和1-苯基-3-甲基-6-硝基-2(1H)-喹喔啉-2-酮均为新化合物,文中给出了它们的重要的分析数据,简要讨论了溶剂在关环反应以及N-烷基化反应中的重要影响,偶然发现以水作溶剂时关环主产物为1-苯基-3-甲基-5-硝基-苯并咪唑.这类化合物可应用于药物,如用作N-甲基-D-天冬氨酸(NMDA)受体及α-氨基羟甲基异噁唑丙酸(AMMPA)受体拮抗剂、杀菌剂等;还可用作植物生长抑制剂、荧光探针以及作为新型功能染料中间体等诸多领域. 相似文献
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《中国化学快报》2023,34(7):108036
The first example of TBAI/H2O cooperative electrocatalytic coupling-annulation of quinoxalin-2(1H)-ones with N-arylglycines was developed. A broad range of tetrahydroimidazo[1,5-a]quinoxalin-4(5H)-ones were obtained in good to excellent yields with exclusive chemoselectivities and excellent regioselectivities. The H-hydrogen bond served as a key factor for the electrocatalytic production of aminomethyl radical at lower oxidative potential. 相似文献
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An acyl radical generation and functionalization strategy through direct photoexcitation of benzothiazolines has been developed. The formed acyl radical species can either be trapped by quinoxalin-2-ones to realize their C(3)-H functionalization or trigger a cascade radical cyclization with isonitriles to synthesise biologically important phenanthridines. The synthetic value of this protocol can be further illustrated by the modification of quinoxalin-2-ones, containing important natural products and drug-based complex molecules. 相似文献
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A facile and metal-free visible-light-enabled three-component reaction of quinoxalin-2(1 H)-ones,alkenes and CF3SO2Na has been developed under air at room temperature.This photocatalytic tandem reaction using 4 CzIPN as the photocatalyst and air as the green oxidant,provides a mild and environmentally friendly approach to access a series of 3-trifluoroalkylated quinoxalin-2(1 H)-ones. 相似文献
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Jian Liu Zhibin Huang Cheng Wang Zefeng Deng Xu Xu Prof. Runsheng Zeng Prof. Yingsheng Zhao 《European journal of organic chemistry》2023,26(15):e202300129
A visible-light-induced Rose bengal catalyzed C3-trifluoroethylation of quinoxalin-2-(1H)-ones is reported. A wide range of quinoxalin-2-(1H)-ones was compatible, which led to the corresponding products in moderate to good yields. A gram-scale reaction proceeded well and afforded an efficient route to prepare C3-trifluoroethylated quinoxalin-2-(1H)-ones. 相似文献
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AbstractOver the past few decades, quinoxalin-2(1H)-one derivatives are serving as active components in diverse families of drugs such as antimicrobial, anticancer, antithrombotic agents and protein kinase inhibitor. Previously, significant attention has been marked for its synthesis and recent years have also observed an upsurge in the modification of this scaffold as well as its functionalization. This review (2008–2020) focused on selective C–H bond functionalization namely arylation, amination, acylation, amidation, alkylation, benzylation, alkoxycarbonylation, cyanoalkylation and phosphorylation etc. at C-3 position of quinoxalin-2(1H)-one. Additionally, alternative complimentary route (radical cyclization protocol) for its synthesis part is well elaborated herein. We also briefly summarized the mechanistic pathway of the C–H bond functionalization approach. 相似文献
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《中国化学快报》2022,33(8):4057-4060
Herein, we report a practical electro-reductive protocol for the direct C–H cyanoalkylation of quinoxalin-2(1H)-ones via iminyl radical-mediated ring opening. These mild reactions proceed under metal-, reductant-, and reagent-free conditions to provide synthetically useful cyanoalkylated quinoxalin-2(1H)-ones. 相似文献
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《中国化学快报》2017,(3)
A series of quinolino[3,4-b]quinoxalin-6(5H)-ones have been synthesized using an Ugi/deprotection/cyclization(UDC) strategy, followed by a nucleophilic aromatic substitution reaction. This facile microwave-assisted method provided good yields and could potentially be used for the construction of a diverse library of quinolino[3,4-b]quinoxalin-6(5H)-ones for high-throughput screening in medicinal chemistry. 相似文献
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Miao Tian Shuyang Liu Dr. Xiubin Bu Dr. Jipan Yu Dr. Xiaobo Yang 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(2):369-373
A practical and scalable protocol for visible-light-accelerated arylation and alkylation of quinoxalin-2(1H)-ones with hydrazines is reported. In this protocol, a hydrazone-based two-dimensional covalent organic frameworks (2D-COF-1) was employed as the heterogeneous photocatalyst (PC). Due to its excellent photocatalytic properties, good chemical stability and heterogeneous nature, the present method exhibits high efficiency, good functional group tolerance, easy scalability and remarkable catalyst reusability. More importantly, it provides an alternative way that allows rapid access to various C3 arylated or alkylated quinoxalin-2(1H)-ones in a greener and sustainable manner. 相似文献
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Ivanova A. E. Khudina O. G. Burgart Ya. V. Saloutin V. I. 《Russian Chemical Bulletin》2011,60(5):937-941
3-Polyfluoroalkyl-1,2-dihydroquinoxalin-2-ones react with 4-bromobutyl acetate to furnish 1-(4-acetoxybutyl)quinoxalin-2-ones
and 2-(4-acetoxybutoxy)quinoxalines in the ratio 2: 1. Deacylation of these compounds under acidic conditions gives the corresponding
1-(4-hydroxybutyl)- and 2-(4-hydroxybutoxy)-substituted quinoxalines. The structures of compounds synthesized were established
by X-ray crystallography, IR spectroscopy, 1H and 19F NMR spectroscopy, GLC-MS. 相似文献
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《中国化学快报》2022,33(4):2036-2040
Herein, an efficient molecular oxygen-mediated method for the selective hydroxyalkylation and alkylation of quinoxalin-2(1H)-ones with alkylboronic acids under transition-metal free conditions has been developed. This strategy demonstrates a broad scope of quinoxalin-2(1H)-ones and alkylboronic acids, giving 3-hydroxyalkylquinoxalin-2(1H)-ones and 3-alkylquinoxalin-2(1H)-ones in moderate-to-good yield. Control experiments reveal that a radical pathway is involved. 相似文献