79506-66-4

Upstream product

• 19488-09-6 sodium 4-methoxyphenylthiolate 
• 107-14-2 chloroacetonitrile 
• 696-63-9 4-Methoxybenzenethiol 
• 75-05-8 acetonitrile 
• 1879-16-9 1-methoxy-4-methylsulfanyl-benzene 
• 6011-14-9 2-aminoacetonitrile hydrochloride 
• 18877-98-0 sodium S-(cyanomethyl)-sulfothioate 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 104-94-9 4-methoxy-aniline 
• 590-17-0 cyanomethyl bromide 
• 28743-98-8 (4-methoxy-phenylsulfanyl)-acetic acid ethyl ester 
• 30893-80-2 4-Methoxyphenyl-mercapto-acetamid 

Downstream Products

• 132276-87-0 2-((4-methoxyphenyl)sulfonyl)acetonitrile 
• 41024-54-8 2-(4-methoxyphenylsulfonyl)-1-phenylethanone 
• 63923-59-1 2-((4-methoxyphenyl)sulfinyl)acetonitrile 

Relevant academic research and scientific papers

Dealkylative intercepted rearrangement reactions of sulfur ylides

Sulfur ylides are well-known to undergo sigmatropic rearrangement reaction. Herein, we describe a novel reactivity of sulfur ylides, which provides access to the product of a formal functional group metathesis upon dealkylative interception of the rearrangement process. Using a simple iron catalyst and in situ generated diazoalkanes this method provides access to α-mercaptoacetonitrile derivatives.

Acrylonitrile derivatives and pharmaceutical composition cpmprising the same

The present invention relates to acrylonitrile compounds and pharmaceutical compositions containing the same, and more particularly, to acrylonitrile compounds and pharmaceutical compositions containing the same, which suppress deformation such as oligome

Cs2CO3-promoted carbon–sulfur bond construction via cross dehydrogenative coupling of thiophenols with acetonitrile

A novel protocol for the construction of carbon–sulfur bonds has been achieved via halogen-free Cs2CO3-promoted cross dehydrogenative coupling (CDC) of thiophenols with acetonitrile. This transformation provides a straightforward route to the synthesis of sulfenylated acetonitriles in up to 80% yield.

Aryl alkyl, aryl aryl thioether compound and its synthesis method

The invention discloses a synthesis method of an aryl-alkyl and aryl-aryl thioether compound represented by a formula (III). According to the synthesis method, aryl tetrafluoroboric acid diazonium salt is taken as a reaction raw material in a reaction solvent, aryl and alkyl thiosulfate is taken as a sulfurizing agent, and the materials react under the catalysis action of visible light and a photosensitive agent to obtain the aryl-alkyl and aryl-aryl thioether compound. According to the synthesis method, the raw materials are easy to obtain and are cheap, the reaction operation is simple, the reaction condition is mild and environment-friendly, the yield is higher, the functional group tolerance is excellent, later modification of drugs is successfully realized, and an efficient C-S bond construction method is provided for medicinal chemistry and biological orthogonal chemistry research.

Mechanistic Study of a Photocatalyzed C-S Bond Formation Involving Alkyl/Aryl Thiosulfate

This study presents thioether construction involving alkyl/aryl thiosulfates and diazonium salt catalyzed by visible-light-excited [Ru(bpy)3Cl2] at room temperature in 44-86 % yield. Electron paramagnetic resonance studies found that thiosulfate radical formation was promoted by K2CO3. Conversely, radicals generated from BnSH or BnSSBn (Bn=benzyl) were clearly suppressed, demonstrating the special property of thiosulfate in this system. Transient absorption spectra confirmed the electron-transfer process between [Ru(bpy)3Cl2] and 4-MeO-phenyl diazonium salt, which occurred with a rate constant of 1.69×109 M-1 s-1. The corresponding radical trapping product was confirmed by X-ray diffraction. The full reaction mechanism was determined together with emission quenching data. Furthermore, this system efficiently avoided the over-oxidation of sulfide caused by H2O in the photoexcited system containing Ru2+. Both aryl and heteroaryl diazonium salts with various electronic properties were investigated for synthetic compatibility. Both alkyl- and aryl-substituted thiosulfates could be used as substrates. Notably, pharmaceutical derivatives afforded late-stage sulfuration smoothly under mild conditions.

A highly efficient Cu-catalyzed S-transfer reaction: From amine to sulfide

A highly efficient Cu-catalyzed dual C-S bonds formation reaction, proceeding in alcohol and water under air, is reported, in which inodorous stable Na2S2O3 is used as a sulfurating reagent. This powerful strategy provides a practical and efficient approach to construct thioethers, using readily available aromatic amines and alkyl halides as starting materials. Sensitive and synthetic useful functional groups could be tolerated. Furthermore, pharmaceuticals, glucose, an amino acid, and a chiral ligand are successfully furnished by this late-stage sulfuration strategy.

Nanomolar potency and metabolically stable inhibitors of kidney urea transporter UT-B

Urea transporters, which include UT-B in kidney microvessels, are potential targets for development of drugs with a novel diuretic ('urearetic') mechanism. We recently identified, by high-throughput screening, a triazolothienopyrimidine UT-B inhibitor, 1, that selectively and reversibly inhibited urea transport with IC50 = 25.1 nM and reduced urinary concentration in mice (Yao et al.J. Am. Soc. Nephrol., in press). Here, we analyzed 273 commercially available analogues of 1 to establish a structure-activity series and synthesized a targeted library of 11 analogues to identify potent, metabolically stable UT-B inhibitors. The best compound, {3-[4-(1,1-difluoroethyl)benzenesulfonyl]thieno[2,3-e][1,2,3]triazolo[1,5-a] pyrimidin-5-yl}thiophen-2-ylmethylamine, 3k, had IC50 of 23 and 15 nM for inhibition of urea transport by mouse and human UT-B, respectively, and ～40-fold improved in vitro metabolic stability compared to 1. In mice, 3k accumulated in kidney and urine and reduced maximum urinary concentration. Triazolothienopyrimidines may be useful for therapy of diuretic-refractory edema in heart and liver failure.

Rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/ arylsulfonyl)acetonitriles: Efficient synthesis of (Z)-β- sulfonylvinylamines and β-Keto sulfones

An efficient rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/arylsulfonyl)acetonitrile is described. Novel β-sulfonylvinylamine products are formed in a stereoselective fashion (Z-alkene). Upon hydrolysis, useful β-keto sulfones are obtained with a broad scope of aryl and sulfonyl substituents.

Intramolecular Stereospecific Pummerer Reactions of Aryl (Substituted-methyl) Sulfoxides Bearing Electron-withdrawing Groups with Acetic Anhydride

The Pummerer reaction of optically active cyanomethyl aryl sulfoxides with acetic anhydride gave the corresponding α-acetoxy sulfides which were induced with a partial asymmetry nearly 30percent at α-carbon, while the 18O-label of the original sulfoxides was retained in more than 85percent in the resulting ester, the Pummerer reaction product.Kinetic experiments with cyanomethyl (p-substituted phenyl) sulfoxides and α,α-dideuterated cyanomethyl p-tolyl sulfoxide in the reaction with acetic anhydride containing a small amount of acetic acid revealed that the rates were correlated with Hammett ?-values and ρ-value of -0.70 was obtained, while the kinetic isotope effect was practically nil, i.e., kH/kD=1.01.These observations indicate clearly that the rearrangement is intramolecular and proceeds via forming a very intimate ion-pair and the rate-determining step is believed to be the S-O bond cleavage after the initial reversible acylation and deprotonation.Elimination of acetic acid proceeds through the Eleb type process.The uneven distribution of 18O in the two oxygens of the resulted ester, i.e., ether and carbonyl oxygens, suggests the recombination of the α-sulfenyl carbonium ion and acetate ion to be very rapid.The pummerer reaction of optically active N,N-dimethyl-p-tolyl-sulfinylacetamide with excess acetic anhydride also gave the corresponding α-acetoxy sulfide in optically active form.In the presence of di-cyclohexylcarbodiimide (DCC), the Pummerer reaction was found to be highly stereoselective affording the corresponding α-acetoxy sulfide with 65percent e.e.Other optically active α-carbonyl-substituted alkyl sulfoxides, i.e., ethyl p-tolylsulfinylacetate and ω-(p-tolylsulfinyl)acetophenone also gave the corresponding highly optically active Pummerer rearrangement products in the treatment with acetic anhydride/DCC system.The Pummerer reaction of the 18O-labeled sulfoxides with acetic anhydride/DCC system gave the corresponding α-acetoxy sulfides which retained much of the original 18O-labels of the sulfoxides.These observations reveal clearly that in the Pummerer reaction of these compounds the acetoxyl migration is intramolecular and takes place through intimate ion-pairs.