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ELECTROCHEMISTRY COMMUNICATIONS · 2019 · IF 4.197

Highly efficient electrochemiluminescence of quinoline and isoquinoline in aqueous solution

Xiangxiang Qin,Xia Xu,Jing Lu,Yinggui Zhu

This paper reports for the first time the strong cathodic electrochemiluminescence (ECL) behavior of quinoline, isoquinoline and their derivatives in aqueous solution with K 2 S 2 O 8 as coreactant. The effects of K 2 S 2 O 8 concentration, pH and scan rate on the ECL intensity have been studied in detail. Calculations of the HOMO-LUMO energy gap for the ECL reaction indicated that isoquinoline is more likely to produce an excited state radical ion than quinoline. The effects of different functional groups on the ECL of isoquinoline were then compared and a possible ECL reaction mechanism was discussed. This work provides a simple and sensitive ECL method for the detection of quinoline and isoquinoline, which are important drug intermediates.

CAS / MDL: 27655-40-9 486-73-7
研究领域: 分析化学 · 药物化学
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APPLIED CATALYSIS A-GENERAL · 2018 · IF 4.521

Highly active and recyclable Pt nanocatalyst for hydrogenation of quinolines and isoquinolines

Xiuru Xue,Min Zeng,Yanhua Wang

Thermoregulated phase-transfer Pt nanocatalyst was shown to be highly active, selective and recyclable in the hydrogenation of quinolines and isoquinolines. The catalyst could be easily separated from the product by simple phase separation and directly reused in the next cycle without evident loss in catalytic activity and selectivity, even after ten recycles. Importantly, for quinoline, the TON of 10,474 is the highest value ever reported among Pt catalysts. More remarkably, for isoquinoline, the TON of 5340 is far ahead of the highest record among transition metal catalysts.

研究领域: 催化化学 · 材料科学 · 有机合成
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CATALYSIS LETTERS · 2025 ·Vol. 155 ·期 5 ·1-9 · IF 2.4

Preparation of Mesoporous Chitosan Cobalt Supported Nano-Catalyst for the Catalyzed Reduction of Quinoline to N-formyltetrahydroquinoline

Wu Lan,Liu Yongchao,Wang Ze,Ye Xinyu,Li Zhenhua,Liu Yaozong

Supported nanocatalysts with environmental sustainability and high catalytic performance have attracted much attention. A supported nanocatalyst Co@NSC has been studied in this paper. Porous materials with catalytic properties were prepared by anchoring transition metal cobalt onto porous materials doped with nitrogen. The results of the scanning electron microscopy (SEM), X-ray diffraction (XRD) and Fourier transform infrared spectroscopy (FT-IR) tests demonstrate that the catalyst obtained exhibits an excellent mesoporous structure and a uniform distribution of cobalt elements. The scaffold is rich in N atoms, which can provide enough anchor sites for cobalt to form cobalt-NX. Cobalt groups can improve the catalytic activity of the catalyst. In addition, Co@NSC is porous, the structure has the potential to facilitate the mass transfer of the reactants. In addition, the porous structure of Co@NSC is beneficial to facilitate the mass transfer of reactant. The prepared catalyst performs well in hydrogenating quinolone to corresponding N-formyltetrahydroquinoline. Subsequently, the selectivity and stability of the prepared catalyst were validated. Graphical abstract

研究领域: 材料科学 · 催化化学
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ENVIRONMENTAL TECHNOLOGY · 2018 · IF 1.666

Modification of biochar by Fe2O3 for the removal of pyridine and quinoline

Hanjiang Xu,Xiaoping Zhang,Yudong Zhang

The biochar produced by pyrolysis at 600°C from powdered mango bark impregnated with iron, namely Fe2O3/biochar, was recognized as a multifunctional material for environmental applications. This work aims at using the above material for the removal of pyridine and quinoline from aqueous solutions. The physico-chemical properties of synthesized biochars were studied systematically with several commonly used material characterization methods including scanning electron microscope (SEM), energy dispersive spectroscopy (EDS), X-ray diffraction (XRD) and Fourier transform infrared spectrometer (FTIR). Structural and morphological analyses of the biochars showed that Fe2O3 particles were nanosized and distributed evenly on the surface of biochar, and thus exhibited great adsorption capacity for the removal of pyridine and quinoline. In addition, the results suggested that the main magnetic phase is maghemite (Fe2O3). The modified biochar showed high removal capacity (99%) for quinoline, but the removal capacity of pyridine was only 73%. The pH experiment in this passage indicated that both pyridine and quinoline reached a maximum adsorption amount at pH near 9.0. Adsorption kinetics suggested that the pseudo-second-order was well fitting the experiment data. The equilibrium study showed that the Langmuir model can adequately describe the adsorption process for pyridine and quinoline. The main mechanism of pyridine and quinoline removal was possibly electrostatic interactions and π–π interactions between the modified biochar and the adsorbate.

研究领域: 环境科学 · 材料科学
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FUEL · 2023 · IF 7.4

N-N self-inhibition effect of aromatic N-heterocyclic compounds on NiWS supported γ-Al2O3 hydrotreating catalyst

Wenbin Huang,Qiang Wei,Haoran Liu,Han Yang,Zhen Xu,Zhengyu Chen,Dongdong Chen,Yasong Zhou

The reason for high-difficulty nitrogen removal of aromatic N-heterocyclic compounds in petroleum fractions was investigated from the main thought of “NiWS property - Reaction behavior - DFT calculation”. The properties of the used catalyst were characterized by a series of techniques with the aim of providing the basis for model construction in the DFT calculations. The kinetic experiments in fixed-bed reactor revealed that although 1,2,3,4-tetrahydroquinoline (THQ1) and decahydroquinoline (DHQ), o-ethylaniline (OEA) exhibited relatively high yields in the HDN reaction of quinoline and indole respectively, they were all able to show high conversions and HDN rates when reacted as feedstocks alone. The study of product normalizations in the reaction system of the mixed feedstocks demonstrated that the difficulty of conversion of THQ1 and DHQ in quinoline HDN was mainly due to the inhibition effect of quinoline feedstock. While in the HDN of indole, the presence of the intermediate product OEA was the main factor for the low conversion of indole. This phenomenon of inhibition originating from within the molecular reaction network was proposed as N-N self-inhibition effect for the first time. The DFT calculations suggested that the inhibition of quinoline on THQ1 could be attributed to the adsorption advantage of quinoline, while the inhibition on DHQ was mainly due to the steric hindrance effect of DHQ itself. And the inhibition effect of OEA on indole can be mainly attributed to its greater nucleophilicity and stronger adsorption ability on the active sites compared with IND.

研究领域: 化学工程 · 催化 · 石油炼制 · 理论化学
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Asian Journal of Organic Chemistry · 2018 ·Vol. 7 ·期 12 ·2527-2533 · IF 2.496

Reaction of Quinoline N-Oxides and Pyridine N-Oxides with Arylzinc Reagents: Synthesis of 2-Arylquinolines and 2-Arylpyridines

Wei-Ze Li,Zhong-Xia Wang

Graphical Reaction of quinoline N -oxides and pyridine N -oxides with arylzinc reagents under transition-metal-free conditions was studied. The reaction was carried out in toluene (for quinoline N -oxides) or THF (for pyridine N -oxides) at 100 °C and required 2 equiv. of arylzinc loadings and the presence of 2.5 equiv. of TFAA, affording 2-arylquinolines and 2-arylpyridines, respectively, in 24% to 95% yields. Reaction of quinoline N -oxides and pyridine N -oxides with arylzinc reagents under transition-metal-free conditions was studied. The reaction was carried out in toluene (for quinoline N -oxides) or THF (for pyridine N -oxides) at 100 °C and required 2 equiv. of arylzinc loadings and the presence of 2.5 equiv. of TFAA, affording 2-arylquinolines and 2-arylpyridines, respectively, in 24% to 95% yields. Functional groups OMe, F, Cl, Br, CF 3 , C(O)NH 2 , COOR and NO 2 were tolerated. Mechanistic studies showed that the reaction of quinoline N -oxides proceeded via a 2-arylquinolin-1(2 H )-olate intermediate, and the reaction of pyridine N -oxides via a 5-arylpenta-2,4-dienal oxime intermediate.

CAS / MDL: 7439-95-4
研究领域: 有机化学 · 合成化学
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Molecular Catalysis · 2023 · IF 4.6

Strengthening spillover hydrogenation of quinoline compounds over platinum-encapsulated amorphized HA zeolite catalyst

Yaozong Tan,Mengxi Han,Pai Peng,Zongyu Sun,Jun Shi,Yong Huang,Junwen Chen,Licheng Bai,Jing Yang,Qiang Chen

Hydrogen spillover has been widely used in heterogeneous catalysis, yet how to explore the potential of catalyst support to further promote catalytic function of hydrogen spillover has rarely been investigated. Herein, platinum encapsulated into amorphized HA zeolite (denoted as Pt@HA) with generated hydroxyl groups was used as model catalyst to study the role of HA zeolite support on the promotion of catalytic performance in hydrogenation of quinolines to tetrahydroquinolines. Benefiting from small pore size of amorphized HA zeolite to prevent direct interaction of quinoline with encapsulated platinum, Pt@HA showed good catalytic selectivity in this transformation through hydrogen spillover. This remarkable catalytic selectivity was resulted from the interaction of hydroxyl groups at surface of HA zeolite with pyridine moiety through the formation N H bond to facilitate adsorption to make much lower apparent activation energy of Pt@HA for hydrogenation of pyridine moiety than that of benzene moiety, thus exhibiting enhanced catalytic selectivity.

CAS / MDL: 12125-02-9
研究领域: 催化 · 化学工程 · 材料科学
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ANALYTICAL SCIENCES · 2021 ·Vol. 37 ·期 2 ·261-266 · IF 2.081

Preparation of Benzyl Quinine-modified Monolithic Column for Reversed-phase Capillary Electrochromatography

Xiangju MAO,Xiaofeng CHENG,Zhenfu LV,Fang XIAO,Lu LIU,Xintao CHENG,Wenshan NI

N-Benzylquininium chloride is a versatile functional monomer with quinoline and benzyl groups, which is beneficial for reversed-phase chromatography. In this study, a novel monolithic column with reversed-phase mode was synthesized using N-benzylquininium chloride as the monomer and 3-(acryloyloxy)-2-hydroxypropyl methacrylate as the cross-linker in a binary porogenic solvent consisting of PEG 400 and a 0.05 M sodium hydroxide aqueous solution. The alkaline solution were found to be useful for the improvement of the mechanical stability of the porous monoliths. The monolithic column showed excellent reversed-phase selectivity and various compounds, such as alkylbenzenes, phenols and polycyclic aromatic hydrocarbons, were separated successfully. The highest column efficiency was 1.75 × 105 N m−1. The relative standard deviations of the migration time for thiourea and four alkylbenzenes were all less than 5.0%, which indicates the monolithic column has good stability. The application of the monolithic column for the analysis of polycyclic aromatic hydrocarbons in spiked lake water samples illustrated its great potential for practical application.

CAS / MDL: 78-67-1
研究领域: 分析化学 · 色谱技术
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PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA · 2022 ·Vol. 120 ·期 1 ·e2209339120 · IF 12.779

Elucidation of the 1-phenethylisoquinoline pathway from an endemic conifer Cephalotaxus hainanensis

Fei Qiao,Yuedong He,Yuhao Zhang,Xuefei Jiang,Hanqing Cong,Zhiming Wang,Huapeng Sun,Yibei Xiao,Yucheng Zhao,Peter Nick

Cephalotaxines harbor great medical potential, but their natural source, the endemic conifer Cephalotaxus is highly endangered, creating a conflict between biotechnological valorization and preservation of biodiversity. Here, we construct the whole biosynthetic pathway to the 1-phenethylisoquinoline scaffold, as first committed compound for phenylethylisoquinoline alkaloids (PIAs), combining metabolic modeling, and transcriptome mining of Cephalotaxus hainanensis to infer the biosynthesis for PIA precursor. We identify a novel protein, ChPSS, driving the Pictet–Spengler condensation and show that this enzyme represents the branching point where PIA biosynthesis diverges from the concurrent benzylisoquinoline-alkaloids pathway. We also pinpoint ChDBR as crucial step to form 4-hydroxydihydrocinnamaldehyde diverging from lignin biosynthesis. The elucidation of the early PIA pathway represents an important step toward microbe-based production of these pharmaceutically important alkaloids resolving the conflict between biotechnology and preservation of biodiversity.

研究领域: 植物生物化学 · 药用植物学 · 生物技术 · 保护生物学
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Journal of Water Process Engineering · 2025 · IF 6.7

Adsorption characteristics and removal mechanism of quinoline in wastewater by walnut shell-based biochar

Yan Cui,Wenrui Du,Yao Zhang,Jifan Hu,Weiwei Kang

Quinoline is a representative refractory ammonia nitrogen contaminant in coking wastewater, which presents a hazard to the environment and humanity. Thus, effective settlement of quinoline is eagerly required. Nevertheless, existing adsorbents are expensive and inefficient in quinoline adsorption. It is significant to explore a low-cost and efficient adsorbent. Herein an environmental-friendly activated biochar derived from agricultural waste walnut shell was synthesized. Activated biochar displays large surface area, rich pores and high surface activity. The adsorption behavior of activated biochar was tested under static and dynamic adsorption systems. Activated biochar represents excellent adsorption performance and industrial application potential. Under the conditions of 298 K, 650 rpm and pH = 7, the activated biochar's saturated adsorption capacity and equilibrium time for quinoline are 342.56 mg g −1 and 20 min, respectively. After five adsorption-desorption cycles, the adsorption capacity retained 93.43 % of the incipient value, indicating that activated biochar exhibits excellent regeneration performance. Moreover, activated biochar could maintain good adsorption performance in real wastewater. More importantly, using walnut shell as the raw material could save costs and realize resource utilization. The negative Δ G θ and positive Δ H θ values demonstrate that the adsorption process is spontaneous and endothermic, which follows the pseudo-first-order kinetics and fits well with the Langmuir–Freundlich model. This work has a good guiding significance in the domain of sewage purification.

CAS / MDL: 91-22-5
研究领域: 环境科学 · 材料科学
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SEPARATION AND PURIFICATION TECHNOLOGY · 2022 · IF 9.136

Enhanced quinoline degradation by persulfate-assisted photocatalytic process with WO3-CuFe2O4 Z-scheme system: Properties and mechanism

Bihan Sun,Houfen Li,Qian Wei,Shuai Xue,Aijuan Zhou,Xiuping Yue

Quinoline is a kind of organic pollutant difficult to be biodegraded, for which the photocatalysis technology is a commonly used removal method, but the degradation performance still needs to be improved. In this work, the WO 3 -CuFe 2 O 4 Z-scheme system was constructed, and the persulfate (PS)-assisted photocatalytic degradation of quinoline with WO 3 -CuFe 2 O 4 by adding persulfate in the photocatalytic systems was studied. The effects of different systems and key parameters such as catalyst dosage, PS concentration and initial pH value on the degradation efficiency of quinoline were investigated. With the addition of persulfate, the degradation efficiency of quinoline increased from 24.3% to 100% in 150 min, under the condition of [PS] = 3 mmol/L, [catalyst] = 3 g/L, temperature = 25 ± 2 °C, and pH = 9. And the WO 3 -CuFe 2 O 4 catalyst showed excellent reusability according to the result of 5-cycle repeated experiment. The possible degradation mechanism was studied by the quenching test and the identification of intermediates and products, which indicated the degradation of quinoline in WO 3 -CuFe 2 O 4 /VIS/PS system was realized via denitrification, dehydrogenation, hydroxylation and ring breaking processes.

研究领域: 环境科学 · 化学工程
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MOLECULES · 2022 ·Vol. 27 ·期 5 ·1537 · IF 4.927

Discovery of Novel 3,4-Dihydro-2(1H)-Quinolinone Sulfonamide Derivatives as New Tubulin Polymerization Inhibitors with Anti-Cancer Activity

Juan Ma,Guo-Hua Gong

In this paper, a small series of novel quinoline sulfonamide derivatives was synthesized, and their structure of the target compounds were confirmed by 1H NMR and MS. The screening of the news target compounds’ in vitro cytotoxic activities against tumor cell lines by the MTT method was performed. Among them, compoundD13(N-(4-methoxybenzyl)-2-oxo-N-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydroquinoline-6-sulfonamide exhibited the strongest inhibitory effect on the proliferation of HeLa (IC50: 1.34 μM), and this value correlated well with the inhibitory activities of the compound against tubulin polymerization (IC50: 6.74 μM). In summary, a new type of quinoline-sulfonamide derivative with tubulin polymerization inhibitory activity was discovered, and it can be used as a lead compound for further modification.Keywords:synthesis;quinoline-sulfonamide;anti-tumor;tubulin polymerization

研究领域: 药物化学 · 肿瘤学
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