An iron(II)‐catalyzed three‐component reaction was developed for the construction of trichloromethylated 3‐benzylquinoxalin‐2(1H)‐ones. This reaction was conducted through the trichloromethylation of ...alkenes with quinoxalin‐2(1H)‐ones using commercially available chloroform as trichloromethyl radical source, which provided a convenient approach toward trichloromethylated 3‐benzylquinoxalin‐2(1H)‐ones.
FeCl3-catalyzed three-component aryl-selenylation of alkenes with good to excellent yields has been disclosed. This method is characterized by synthesis of complicated products in a single-step ...reaction, simple operation and readily available commercially reagents. Finally, a reasonable mechanism of FeCl3-catalyzed aryl-selenylation is proposed.
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Abstract
A strategy for the synthesis of diverse protected α‐monofluoro‐γ‐amino acid derivatives has been developed. This reaction assembles a simple enamide, quinoxalin‐2(1
H
)‐one, and diethyl ...2‐bromo‐2‐fluoromalonate through a three‐component reaction driven by visible light. The advantages of this protocol include the simplicity of its operation, mild conditions, high functional group tolerance, and applicability to a wide variety of substrates. The synthesis of this fluorine‐containing amino acid derivative has significant value for potential applications in medicinal chemistry and chemical biology.
A green and stable magnetic Fe3O4 core encapsulated in porous carbon shell was prepared. Then, the surface of as‐synthesized Fe3O4@meso‐C immobilized with activated 4‐aminobenzenesulfonic acid to ...achieve Fe3O4@C/Ph—SO3H. Structural, physico‐chemical, and magnetic properties of synthesized Fe3O4@C/Ph—SO3H catalyst using various analyses such as FT‐IR spectroscopy, TGA, XRD, SEM, TEM. EDX, and VSM were investigated. Fe3O4@C/Ph—SO3H was used as a stable and recoverable acid catalyst for regioselective three‐component synthesis of tetrazoloquinazolines under mild conditions. This catalyst offers a green protocol of one pot due to having active SO3H groups, reacting in mild conditions with high yield and ability to recover and reuse without significant loss in activity.
Multi‐step synthesized Fe3O4@C/Ph‐SO3Hwas used as a recoverable acid catalyst for regioselective synthesis oftetrazoloquinazolines. This catalyst offers a green protocol due to havingactive SO3H groups, reacting in mild conditions with high yield.
A simple method for the synthesis of monoselenides and diselenides having 1,2,3-triazole ring is described herein. The three component reaction of ethynylstibanes, organic azides, and selenium powder ...is catalyzed by CuI (10 mol%) using 1,10-phenanthroline as the ligand (10 mol%) under aerobic conditions. Either selenides or diselenides can be synthesized by selecting the appropriate amount of selenium powder for otherwise identical reaction conditions. The obtained selenides and diselenides having a 1,2,3-triazole ring are all novel compounds. By using an antimony reagent, this one-pot reaction provides regioselective double Se-arylation under simple reaction conditions.
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•The Cu-catalyzed three-component reaction of organoantimony, azides, and selenium is described.•The obtained selenides and diselenides having a 1,2,3-triazole ring are all novel compounds.•This reaction provides regioselective double Se-arylation under simple reaction conditions.
In this study, the metal complex (5,10,15,20‐tetrakis‐(4‐sulfonatophenyl)‐porphyrin manganese (III) chloride; denoted as MnTSPP) represents a promising efficient and reusable heterogeneous solid ...catalyst for facile and highly efficient one‐pot synthesis of 1,4 dihydropyridine derivatives via three‐component condensation reaction of aromatic aldehyde, ethyl acetoacetate, and ammonium acetate under green and mild reaction conditions. The simple operation, short reaction time (15 min), and the high efficiency (99%) are the special advantage of this protocol. Furthermore, the green aspects of this synthetic protocol were more studied by examination of the reusability of MnTSPP for four consecutive cycles without a significant loss of catalytic activity. Remarkably, the new synthesis presented advantages in terms of safety, commercially available catalyst, simplicity, stability, mild conditions, short reaction time, and excellent yields, using a mixture of H2O and C2H5OH environmental‐friendly solvent, operationally facile, wide tolerance of starting materials, and excellent recoverable of the catalyst.
The green aspects of this synthetic protocol were more studied by examination of the reusability of MnTSPP for four consecutive cycles without the significant loss of catalytic activity. The new synthesis presented remarkably advantages in terms of safety, simplicity, stability, mild conditions, short reaction time, and excellent yields.
Herein, we outline a highly efficient PEG‐4000‐mediated one‐pot three‐component reaction for the synthesis of 3‐imidazolyl indole clubbed 1,2,3‐triazole derivatives (5a–r) at up to 96% yield as ...antiproliferative agents. This three‐component protocol offers the advantages of an environmentally benign reaction, excellent yield, quick response time, and operational simplicity triggered by the copper catalyst under microwave irradiation. All the synthesized compounds were tested for antiproliferative activity against six human solid tumor cell lines, that is, A549 and SW1573 (nonsmall cell lung), HBL100 and T‐47D (breast), HeLa (cervix), and WiDr (colon). Among them, six compounds, 5g–j, 5m, and 5p, demonstrated effective antiproliferative action with GI50 values under 10 μM. Furthermore, density functional theory (DFT) calculations were performed for all the synthesized molecules through geometry optimizations, frontier molecular orbital approach, and molecular electrostatic potential (MESP). The theoretical DFT calculation was performed using the DFT/B3LYP/6‐31+G (d,p) basis set. Moreover, the biological reactivity of all the representative synthesized molecules was compared with the theoretically calculated quantum chemical descriptors and MESP 3D plots. We also investigated the drug‐likeness characteristic and absorption, distribution, metabolism, excretion, and toxicity (ADMET) prediction. In general, our approach enables environmentally friendly access to 3‐imidazolyl indole clubbed 1,2,3‐triazole derivatives as prospective antiproliferative agents.
The reported three‐component approach has the advantages of a microwave‐activated copper catalyst, excellent yield, short response time, and operational simplicity. All the synthesized compounds were tested for antiproliferative activity against six human solid tumor cell lines. Density functional theory calculations were performed and the drug‐likeness characteristics and absorption, distribution, metabolism, excretion, and toxicity (ADMET) profiles were determined.
•Synthesis of new 6-(4-metoxyphenyl)−4-phenyl-1,2-dihydropyrimidin-2-one using multicomponent reactions.•Structure was confirmed by single-crystal XRD.•Hirshfeld analysis was used to delineate the ...intermolecular contacts.•FMO, MEP, NBO, and NLO analysis were investigated using the DFT method.•Molecular docking study was performed.
The three-component condensation reaction of 4-methoxybenzaldehyde with acetophenone and urea in the presence of CF3COOH was investigated and as a result, 6-(4-methoxyphenyl)-4-phenyl-1,2-dihydropyrimidine-2-one was synthesized. The structure of the synthesized compound was confirmed by the X-ray method. Both the DFT and TD-DFT computations for comprehensive analysis of spectral data, and electronic parameters were carried out as an add-on to synthetic research and well corroborated with the experimental results. NBO, NLO, and Hirshfeld surface and energy framework analysis were also used to segregate the different intermolecular hydrogen bonds involved in the molecular packing strength. All DFT findings imply that the synthesized molecule has enhanced non-linear optical properties increased charge transfer and is a highly stable, and proactive candidate for drugs. Furthermore, molecular docking studies were carried out to investigate the binding mechanism between 6-(4-metoxyphenyl)-4-phenyl-1,2-dihydropyrimidin-2-one and the thioredoxin glutathione reductase (TGR) complex. ADMET parameter analysis was also carried out for the compound to understand the compound's safety and compound efficiency for the drug candidate.
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An ultrasound-promoted three-component halogenation-azaheteroarylation of alkenes with imidazo1,2-apyridines and NXS (X = Br or Cl) under catalyst-free and additive-free conditions ...has been achieved. With good regioselectivity and functional group tolerance, the reaction provided mild and rapid access to β-halogen-functionalized imidazo1,2-apyridines via tandem carbon-halogen and carbon–carbon bond formation. The strategy could also be appropriate for some other aza-heterocycles.
A route to γ‐keto sulfones through a metal‐free reaction of cyclopropanols, DABCO ⋅ (SO2)2 and alkyl halides is described. This reaction occurs under mild conditions in the absence of any catalysts, ...additives, or oxidants. Various functional groups including as ester, amino, methoxy, bromo, trifluoromethyl, nitro and carbonyl are tolerated well in this transformation, and the corresponding γ‐keto sulfones are afforded in 35% to 95% yields. The proposed mechanism implies that this reaction proceeds through γ‐keto sulfinate intermediate generated in situ, which further undergoes nucleophilic substitution with alkyl halides leading to γ‐keto sulfones.
