80172-73-2

Usage

Structure

Pyrrolidinedione derivative with a thioether group attached to a methoxyphenyl ring

Type

Chemical compound

Potential applications

Drug or research chemical with reported pharmacological activity (although specific details are limited)

Possible uses

Organic synthesis or medicinal chemistry (as a thioether derivative)

Additional notes

Further investigation into its potential applications is warranted.

Upstream product

• 128-08-5 N-Bromosuccinimide 
• 5335-87-5 4,4'-dimethoxyphenyl disulfide 
• 128-09-6 N-chloro-succinimide 
• 696-63-9 4-Methoxybenzenethiol 
• 3481-09-2 N-chlorophthalimide 
• 123-56-8 Succinimide 

Downstream Products

• 80172-68-5 7α-(4-methoxyphenylthio)-nupharidin-6-ol 
• 80172-61-8 7β-(4-methoxyphenylthio)-nupharidin-6-ol 
• 139461-66-8 2-<(4-methoxyphenyl)thio>indole 
• 1605324-30-8 hex-1-yn-1-yl(4-methoxyphenyl)sulfane 
• 33720-25-1 1-(4-methoxyphenyl)hexane-1,2-dione 
• 89478-04-6 2-[(4-methoxyl)phenylthio]-1,4-naphthoquinone 
• 128958-95-2 2-((4-methoxyphenyl)thio)benzonitrile 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 

Relevant academic research and scientific papers

Regioselective C-H Thioarylation of Electron-Rich Arenes by Iron(III) Triflimide Catalysis

A mild and regioselective method for the preparation of unsymmetrical biaryl sulfides using iron(III) catalysis is described. Activation of N-(arylthio)succinimides using the powerful Lewis acid iron(III) triflimide allowed the efficient thiolation of a range of arenes, including anisoles, phenols, acetanilides, and N-heterocycles. The method was applicable for the late-stage thiolation of tyrosine and tryptophan derivatives and was used as the key step for the synthesis of pharmaceutically relevant biaryl sulfur-containing compounds such as the antibiotic dapsone and the antidepressant vortioxetine. Kinetic studies revealed that while N-(arylthio)succinimides bearing electron-deficient arenes underwent thioarylation catalyzed entirely by iron(III) triflimide, N-(arylthio)succinimides with electron-rich arenes displayed an autocatalytic mechanism promoted by the Lewis basic product.

3-Thiolated pyrroles/pyrrolines: controllable synthesis and usage for the construction of thiolated fluorophores

Thiolation/cyclization of homopropargylic tosylamides allowed the selective synthesis of 3-thiolated pyrroles and pyrrolines controlled by solvents. Moreover, the desired 3-thiolated pyrroles were readily transformed to organic fluorophores benzothienopyrrole and bisthiolated boron dipyrromethene (S-BODIPY).

Enantioselective Construction of Axially Chiral Amino Sulfide Vinyl Arenes by Chiral Sulfide-Catalyzed Electrophilic Carbothiolation of Alkynes

The enantioselective construction of axially chiral compounds by electrophilic carbothiolation of alkynes is disclosed for the first time. This enantioselective transformation is enabled by the use of a Ts-protected bifunctional sulfide catalyst and Ms-protected ortho-alkynylaryl amines (Ts=tosyl; Ms=mesyl). Both electrophilic arylthiolating and electrophilic trifluoromethylthiolating reagents are suitable for this reaction. The obtained products of axially chiral vinyl–aryl amino sulfides can be easily converted into biaryl amino sulfides, biaryl amino sulfoxides, biaryl amines, vinyl–aryl amines, and other valuable difunctionalized compounds.

Design synthesis and evaluation of novel aldose reductase inhibitors: The case of indolyl–sulfonyl–phenols

Therapeutic interventions with aldose reductase inhibitors appear to be a promising approach to major pathological conditions (i.e. neuropathy/angiopathy related to chronic hyperglycemia, chronic inflammation and cancer). Until now, the most potent aldose

Stereoretentive C(sp3)-S Cross-Coupling

We report a stereoretentive cross-coupling reaction of configurationally stable nucleophiles with disulfide and N-sulfenylsuccinimide donors promoted by Cu(I). We demonstrate the utility of this method in the synthesis of thioglycosides derived from simple alkyl and aryl thiols, thioglycosides, and in the glycodiversification of cysteine residues in peptides. These reactions operate well with carbohydrate substrates containing common protective groups and reagents with free hydroxyl and secondary amide functionalities under standardized conditions. Competition experiments in combination with computational DFT studies established that the putative anomeric intermediate is an organocopper species that is configurationally stable and resistant to epimerization due to its short lifetime. The subsequent reductive elimination from the Cu(III) intermediate is rapid and stereoretentive. Taken together, the glycosyl cross-coupling is ideally suited for late stage glycodiversification and bioconjugation under highly controlled installation of the aliphatic carbon-sulfur bonds.

h-BN@Copper(II) nanomaterial catalyzed cross-coupling reactions between sulfoximines and N-(phenylthio)-succinimide under mild condition

A novel and efficient method for the synthesis of N-S substituted sulfoximines has been established with h-BN-supported copper(II) nanomaterial as the catalyst. Catalyzed by this heterogeneous catalyst, the desired products were obtained with wide scope of substrates, good to excellent yields, free ligand and low-toxicity solvent. Moreover, after being reused ten times, there is almost no significant loss of its catalytic activity.

A facile synthesis of 3,4-dimercaptofurans via sulfenylation of (E)-β-chlorovinyl ketones and 1,2-sulfur migration

The one-pot sulfenylation of (E)-β-chlorovinyl ketones was investigated under soft α-vinyl enolization conditions. Modulating the nature of nucleophilic species using a “hard” base the regioselective formation of α,γ-dithio-allenyl ketones has been achieved, where the thermodynamic control was mimicked by the presence of Et3N·HCl. The sulfenylated products, α,γ-dithio-allenyl and α,α-dithio-propargyl ketones, smoothly underwent cycloisomerization to 3,4-dimercaptofurans via a novel 1,2-sulfur migration in excellent yields.

Synthesis of 3-Sulfenylated Coumarins: BF3·Et2O-Mediated Electrophilic Cyclization of Aryl Alkynoates Using N-Sulfanylsuccinimides

A simple and efficient metal-free sulfenylation/cyclization of aryl alkynoates has been developed, obtaining various 3-sulfenylated coumarins in moderate to excellent yields. In the presence of BF3·Et2O, the stable and readily access

Synthesis of Aryl Sulfides: Metal-Free C-H Sulfenylation of Electron-Rich Arenes

A simple, efficient, and practical metal-free C-H sulfenylation of substituted electron-rich arenes has been developed. This method is highly regioselective, and the corresponding aryl sulfides were obtained in moderate to excellent yields from stable and

TFA-promoted direct C-H sulfenylation at the C2 position of non-protected indoles

A simple, efficient and practical metal-free C-H sulfenylation process at the C2 position of non-protected indoles has been developed. 2-Thioindoles were obtained in moderate to high yields using stable and readily available N-(thio)succinimides at room temperature in the presence of TFA.