Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

I₂-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot.

ABSTRACT: An efficient approach for the synthesis of 1,2-diaryl diketones was developed from readily available α-methylene ketones by catalysis of I₂. In the same oxidation system, a novel one-pot procedure was established for the construction of antiviral and anticancer quinoxalines. The reactions proceeded well with a wide variety of substrates and good functional group tolerance, affording desired compounds in moderate to excellent yields. Quinoxalines 4ca and 4ad inhibited viral entry of SARS-CoV-2 spike pseudoviruses into HEK-293T-ACE2^h host cells as dual blockers of both human ACE2 receptor and viral spike RBD with IC₅₀ values of 19.70 and 21.28 μM, respectively. In addition, cytotoxic evaluation revealed that 4aa, 4ba, 4ia, and 4ab suppressed four cancer cells with IC₅₀ values ranging from 6.25 to 28.55 μM.

SUBMITTER: Kong L

PROVIDER: S-EPMC8757360 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

I2-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot.

Kong Lingkai L Meng Jieru J Tian Wenyue W Liu Jiazheng J Hu Xueping X Jiang Zhi-Hong ZH Zhang Wei W Zhang Wei W Li Yanzhong Y Bai Li-Ping LP

ACS omega 20211221 1

An efficient approach for the synthesis of 1,2-diaryl diketones was developed from readily available α-methylene ketones by catalysis of I2. In the same oxidation system, a novel one-pot procedure was established for the construction of antiviral and anticancer quinoxalines. The reactions proceeded well with a wide variety of substrates and good functional group tolerance, affording desired compounds in moderate to excellent yields. Quinoxalines 4ca and 4ad inhibited viral entry of SA ...[more]

PMID: 35036799

Similar Datasets

TBAI-Catalyzed Oxidative Coupling of Benzyl Ketones to Synthesize 2,3-Diaryl-1,4-Diketones in Water.

Project description:An efficient and green route of C-C bond formation was disclosed to construct 2,3-diaryl-1,4-diketones from α-methylene ketones by the catalysis of tetrabutylammonium iodide (TBAI) with tert-butyl hydroperoxide (TBHP) as an oxidant in water. This reaction affords the desired products in good to excellent yields from readily available materials, with a broad substrate scope, good functional group tolerance, and mild reaction conditions. Furthermore, tetrasubstituted furan and pyrrole were smoothly constructed from α-methylene ketones in one pot with 96 and 90% yields, respectively.

| S-EPMC8772304 | biostudies-literature

Iodine-Mediated Oxidative Rearrangement of α,β-Unsaturated Diaryl Ketones: A Facile Access to 1,2-Diaryl Diketones.

Project description:A metal-free oxidative rearrangement was explored for the synthesis of 1,2-diaryl diketones by utilizing α,β-unsaturated diaryl ketones and I2/TBHP in good to high yields. The reaction proceeds via oxidative aryl migration, followed by C-C bond cleavage. A simple and high-yielding protocol was developed for the synthesis of a wide range of 1,2-diaryl diketones, which are the backbone for a variety of medicinally important molecules.

| S-EPMC6648810 | biostudies-literature

A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH4I.

Project description:The electrochemical preparation of 2-aminothiazoles has been achieved by the reaction of active methylene ketones with thioureas assisted by ᴅʟ-alanine using NH4I as a redox mediator. The electrochemical protocol proceeds in an undivided cell equipped with graphite plate electrodes under constant current conditions. Various active methylene ketones, including β-keto ester, β-keto amide, β-keto nitrile, β-keto sulfone and 1,3-diketones, can be converted to the corresponding 2-aminothiazoles. Mechanistically, the in situ generated α-iodoketone was proposed to be the key active species.

| S-EPMC9490072 | biostudies-literature

InCl3-Catalyzed One-Pot Synthesis of Pyrrolo/Indolo- and Benzooxazepino-Fused Quinoxalines.

Project description:In this paper, we describe an efficient InCl3-catalyzed two-component reaction of 1-(2-aminophenyl)pyrroles/indoles and 2-propargyloxybenzaldehydes for the direct synthesis of 12bH-benzo[6,7]1,4-oxazepino[4,5-a]pyrrolo/indolo[2,1-c]quinoxalines. This high atom- and step-economical one-pot process generates three new C/N-C bonds in a single synthetic operation, resulting in the formation of new six- and seven-membered heterocyclic rings. The easy availability of the starting materials, the use of the relatively inexpensive indium catalyst, and the good substrate scope are the salient features of this strategy. The proposed mechanistic pathway involves imine formation, two consecutive cyclizations via electrophilic aromatic substitution and nucleophilic addition reactions, and the H shift step.

| S-EPMC11292660 | biostudies-literature

Visible light-promoted CO2 fixation with imines to synthesize diaryl α-amino acids.

Project description:Light-mediated transformations with CO2 have recently attracted great attention, with the focus on CO2 incorporation into C-C double and triple bonds, organohalides and amines. Herein is demonstrated visible light -mediated umpolung imine reactivity capable of engaging CO2 to afford α-amino acid derivatives. By employing benzophenone ketimine derivatives, CO2 fixation by hydrocarboxylation of C=N double bonds is achieved. Good to excellent yields of a broad range of α,α-disubstituted α-amino acid derivatives are obtained under mild conditions (rt, atmospheric pressure of CO2, visible light). A procedure that avoids tedious chromatographic purification and uses sustainable sunlight is developed to highlight the simplicity of this method.

| S-EPMC6250672 | biostudies-literature

"One-Pot" CuCl2-Mediated Condensation/C-S Bond Coupling Reactions to Synthesize Dibenzothiazepines by Bi-Functional-Reagent N, N'-Dimethylethane-1,2-Diamine.

Project description:The efficient "One-pot" CuCl2-catalyzed C-S bond coupling reactions were developed for the synthesis of dibenzo[b,f][1,4]thiazepines and 11-methy-ldibenzo[b,f][1,4]thiazepines via 2-iodobenzaldehydes/2-iodoacetophenones with 2-aminobenzenethiols/2,2'-disulfanediyldianilines by using bifunctional-reagent N, N'-dimethylethane-1,2-diamine (DMEDA), which worked as ligand and reductant. The reactions were compatible with a range of substrates to give the corresponding products in moderate to excellent yields.

| S-EPMC9656399 | biostudies-literature

An iodine/DMSO-catalyzed sequential one-pot approach to 2,4,5-trisubstituted-1H-imidazoles from α-methylene ketones.

Project description:A sequential one-pot approach to 2,4,5-trisubstituted imidazoles has been developed from α-methylene ketones and aldehydes. This methodology employs air-moisture stable reaction conditions and an inexpensive iodine/DMSO system affording a diverse range of known and novel (substrate scope) 2,4,5-trisubstituted imidazoles in moderate to excellent yields. The iodine/DMSO system was extended to the domino convergent synthesis of two functionalized intermediates, benzil and benzaldehyde, to produce the final product.

| S-EPMC9089320 | biostudies-literature

A new route to synthesize aryl acetates from carbonylation of aryl methyl ethers.

Project description:Ether bond activation is very interesting because the synthesis of many valuable compounds involves conversion of ethers. Moreover, C-O bond cleavage is also very important for the transformation of biomass, especially lignin, which abundantly contains ether bonds. Developing efficient methods to activate aromatic ether bonds has attracted much attention. However, this is a challenge because of the inertness of aryl ether bonds. We proposed a new route to activate aryl methyl ether bonds and synthesize aryl acetates by carbonylation of aryl methyl ethers. The reaction could proceed over RhCl3 in the presence of LiI and LiBF4, and moderate to high yields of aryl acetates could be obtained from transformation of various aryl methyl ethers with different substituents. It was found that LiBF4 could assist LiI to cleave aryl methyl ether bonds effectively. The reaction mechanism was proposed by a combination of experimental and theoretical studies.

| S-EPMC5959316 | biostudies-literature

Green Synthesis of Indeno[1,2-b]quinoxalines Using β-Cyclodextrin as Catalyst.

Project description:An efficient, mild, and green method was developed for the synthesis of indeno[1,2-b]quinoxaline derivatives via o-phenylenediamine (OPD) and 2-indanone derivatives utilizing β-cyclodextrin (β-CD) as the supramolecular catalyst. The reaction can be carried out in water and in a solid state at room temperature. β-CD can also catalyze the reaction of indan-1,2-dione with OPD with a high degree of efficiency. Compared to the reported methods, this procedure is milder, simpler, and less toxic, making it an eco-friendly alternative. In addition, the β-CD can be recovered and reused without the loss of activity.

| S-EPMC8779894 | biostudies-literature

A facile route to synthesize n-SnO2/p-CuFe2O4 to rapidly degrade toxic methylene blue dye under natural sunlight.

Project description:In the present study, the n-SnO2/p-CuFe2O4 (p-CFO) complex was prepared by a two-step process. p-CFO synthesized by the molten salt method was coated with SnO2 synthesized by a facile in situ chemical precipitation method. The formation of n-SnO2/p-CFO was confirmed by powder X-ray diffraction (PXRD). Scanning electron microscopy (SEM) images showed that the sharp edges of uncoated pyramid-like p-CFO particles were covered by a thick layer of n-SnO2 on coated p-CFO particles. The complete absence of Cu and only 3 wt% Fe on the surface of the n-p complex observed in the elemental analysis using energy-dispersive X-ray spectroscopy (EDX) on the n-p complex confirmed the presence of a thick layer of SnO2 on the p-CFO surface. Diffuse reflectance spectroscopy (DRS) was employed to elucidate the bandgap engineering. The n-SnO2/p-CFO complex and p-CFO showed 87% and 58.7% methylene blue (MB) degradation in 120 min under sunlight, respectively. The efficiency of the n-p complex recovered after 5 cycles (73.5%) and was found to be higher than that of the uncoated p-CFO (58.7%). The magnetically separable property of the n-p complex was evaluated by using vibration sample magnetometry (VSM) measurements and it was confirmed that the prepared photocatalyst can be easily recovered using an external magnet. The study reveals that the prepared complex could be a potential candidate for efficient photodegradation of organic dyes under sunlight due to its efficient recovery and reusability owing to its magnetic properties.

| S-EPMC9169069 | biostudies-literature