7205-60-9

Upstream product

• 74-96-4 ethyl bromide 
• 824-78-2 4-nitrophenol sodium salt 
• 636-98-6 p-nitrobenzene iodide 
• 994-45-6 triethyl(ethylthio)stannane 
• 100-25-4 para-dinitrobenzene 
• 14252-42-7 acetaldehyde diethyl dithioacetal 
• 13113-79-6 sodium 4-nitrobenzenethiolate 
• 591-96-8 penta-2,3-diene 
• 130436-15-6 2-methyl-2-butyl 4-nitrobenzenesulfenate 
• 598-25-4 Dimethylallene 
• 130436-14-5 C₉H₁₁NO₃S 
• 45797-13-5 4-nitrophenylthiolate 
• 75-03-6 ethyl iodide 
• 1849-36-1 para-nitrobenzenethiol 

Downstream Products

• 7205-81-4 1-(ethylsulfonyl)-4-nitrobenzene 
• 3463-02-3 4-(ethylthio)aniline 
• 861551-20-4 N,N'-bis-(4-ethylsulfanyl-phenyl)-hydrazine 
• 64-17-5 ethanol 
• 7205-70-1 (R,S)-1-(ethylsulfinyl)-4-nitrobenzene 
• 15481-55-7 4-Nitrobenzenesulfonic acid ethyl ester 
• 75-07-0 acetaldehyde 
• 27978-16-1 N-(4-(ethylthio)phenyl)acetamide 
• 851008-74-7 (R,S)-S-ethyl-S-(4-nitrophenyl)sulfoximide 
• 1223498-62-1 (R,S)-S-ethyl-S-(4-nitrophenyl)-N-(trifluoroacetyl)sulfoximide 
• 1223498-67-6 (S)-S-cyclopropyl-S-(4-{[4-{[(1R, 2R)-2-hydroxy-1-methylpropyl]oxy}-5-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)sulphoximide 
• 1223498-69-8 (R)-S-cyclopropyl-S-(4-{[4-{[(1R, 2R)-2-hydroxy-1-methylpropyl]oxy}-5-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)sulphoximide 
• 851008-62-3 (R,S)-N-(ethoxycarbonyl)-S-ethyl-S-(4-nitrophenyl)sulfoximide 
• 851007-68-6 (R,S)-S-[4-({5-bromo-4-[(1R,2R)-(2-hydroxy-1-methylpropyl)amino]pyrimidin-2-yl}amino)phenyl]-N-(ethoxycarbonyl)-S-ethylsulfoximide 

Relevant academic research and scientific papers

C-S coupling with nitro group as leaving group via simple inorganic salt catalysis

An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition-elimination mechanism.

C-H Alkenylation of Heteroarenes: Mechanism, Rate, and Selectivity Changes Enabled by Thioether Ligands

Thioether ancillary ligands have been identified that can greatly accelerate the C-H alkenylation of O-, S-, and N-heteroarenes. Kinetic data suggest thioether-Pd-catalyzed reactions can be as much as 800× faster than classic ligandless systems. Furthermore, mechanistic studies revealed C-H bond cleavage as the turnover-limiting step, and that rate acceleration upon thioether coordination is correlated to a change from a neutral to a cationic pathway for this key step. The formation of a cationic, low-coordinate catalytic intermediate in these reactions may also account for unusual catalyst-controlled site selectivity wherein C-H alkenylation of five-atom heteroarenes can occur under electronic control with thioether ligands even when this necessarily involves reaction at a more hindered C-H bond. The thioether effect also enables short reaction times under mild conditions for many O-, S-, and N-heteroarenes (55 examples), including examples of late-stage drug derivatization.

3-PHOSPHOGLYCERATE DEHYDROGENASE INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Copper nanoparticles supported on polyaniline-functionalized multiwall carbon nanotubes: An efficient and recyclable catalyst for synthesis of unsymmetric sulfides using potassium ethyl xanthogenate in water

A new and powerful polyaniline-functionalized carbon nanotube-supported copper(II) nanoparticle catalyst was successfully prepared and evaluated as a heterogeneous catalyst for the one-pot synthesis of unsymmetric thioethers by coupling of aryl, alkyl and benzyl halides using potassium ethyl xanthogenate as source of sulfur in water. All of these reactions gave the desired products in good to excellent yields. The catalyst is available, air-stable and can be reused several times without significant loss in its catalytic activity.

SULFOXIMINE-SUBSTITUTED ANILINOPYRIMIDINE DERIVATIVES AS CDK INHIBITORS, THE PRODUCTION THEREOF, AND USE AS MEDICINE

The invention relates to sulfoximine-substituted anilino-pyrimidine derivatives of formula (I). methods of production thereof, and use thereof as medication for the treatment of various diseases.

A kinetic investigation, supported by theoretical calculations, of steric and ring strain effects on the oxidation of sulfides and sulfoxides by dimethyldioxirane in acetone

The oxidations of alkyl 4-nitrophenyl, and dialkyl, sulfides and sulfoxides by dimethyldioxirane in acetone occur by concerted mechanisms but the sulfides respond differently from the sulfoxides to variation in the alkyl group. The reactions of the sulfides are inhibited by the steric effects of alkyl groups and these predominate over their inductive effects. By contrast, the reactions of these limited sets of sulfoxides are insensitive to alkyl steric effects but there is an indication of steric acceleration when a broader set of sulfoxides is considered. This behaviour is rationalised in terms of the differences in dipolar charge and its solvation between the ground state and transition state for the two types of substrate. The oxidations of cyclic sulfides and sulfoxides also exhibit contrasting behaviour. The reactivity of the sulfides is insensitive to ring strain but is explicable in frontier orbital terms whereas that of the sulfoxides is partly dependent upon the change in ring strain between reactant and product on oxidation, a difference rationalised in terms of the relative positions of the transition states in the reaction coordinates of the two oxidations. The reactivity of 4-, 5- and 6-membered cyclic sulfoxides is also dependent on a ring-size related property of the transition state. Calculations at the B3-LYP/6-31G* level of density functional theory on both ground states and transition states, including simulation of solvation by acetone, strongly support the mechanistic conclusions reached in this and earlier work.

Synthesis of aryl sulfides by decarboxylative C-S cross-couplings

A study was conducted to demonstrate the transition-metal-catalyzed synthesis of aryl sulfides by decarboxylative C-S cross-couplings. Coupling reaction of 2-nitrobenzoic acid with 1-octanethiol were carried in the presence of different combinations of tr

Sulfite-promoted one-pot synthesis of sulfides by reaction of aryl disulfides with alkyl halides

A sodium dithionite, sodium thiosulfate and rongalite promoted one-pot synthesis of aryl alkyl sulfides at room temperature has been developed. The reactions of a range of disulfides with alkyl halides proceeded smoothly in the presence of rongalite. Possible reaction pathways are discussed and the effects of these sulfites on disulfides are investigated. The important features of this protocol are metal-free, strong-base-free, and mild reaction conditions, operational simplicity, short reaction times and high yields of products. Georg Thieme Verlag Stuttgart.

One-pot synthesis of sulfides by reaction of disulfides with alkyl halides in the presence of sodium dithionite

Sodium dithionite-promoted synthesis of unsymmetrical diorganyl sulfides by a reaction of diaryl disulfides with alkyl halides at r.t. has been developed. The advantages offered by this method are operational simplicity, a faster reaction, neutral and mild reaction conditions, and moderate to good yields of products.

CsF-Celite, an efficient solid state reagent for the syntheses of thioesters and thioethers

Coupling reactions of a number of aliphatic, aromatic, and heterocyclic compounds bearing an acidic hydrogen atom attached to sulfur, with alkyl, acyl, benzyl, or benzoyl halides in acetonitrile with cesium fluoride-Celite are described. This procedure is convenient, efficient, and practical for the preparation of thioethers and thioesters. Springer-Verlag 2005.