51290-78-9

Upstream product

• 19829-29-9 4-pyridinethione 
• 100-39-0 benzyl bromide 
• 5421-92-1 1-(4-pyridyl)pyridinium chloride hydrochloride 
• 100-44-7 benzyl chloride 
• 78526-40-6 4'-Benzylsulfanyl-4'H-[1,1']bipyridinyl-4-one 
• 71831-63-5 4'-Benzylsulfanyl-2,6-dimethyl-4'H-[1,1']bipyridinyl-4-one 
• 4556-23-4 pyridine-4-thiol 
• 66134-95-0 pyridyl-4-thiolate sodium salt 
• 100-51-6 benzyl alcohol 
• 626-61-9 4-Chloropyridine 
• 19524-06-2 4-bromopyridine hydrochloride 
• 100-53-8 phenylmethanethiol 
• 78526-32-6 2,6-Dimethyl-4'-p-tolylsulfanyl-4'H-[1,1']bipyridinyl-4-one 
• 78526-43-9 4'-Benzylsulfanyl-2-methyl-4'H-[1,1']bipyridinyl-4-one 

Downstream Products

• 101736-20-3 4-[(phenylmethyl)sulfonyl]pyridine 
• 89818-48-4 4-[(phenylmethyl)sulfinyl]pyridine 

Relevant academic research and scientific papers

Promoting Effect of Crystal Water Leading to Catalyst-Free Synthesis of Heteroaryl Thioether from Heteroaryl Chloride, Sodium Thiosulfate Pentahydrate, and Alcohol

It is observed the crystal water in sodium thiosulfate pentahydrate (Na2S2O3·5H2O) can promote its multicomponent reaction with heteroaryl chlorides and alcohols, providing a facile, green, and specific synthesis of unsymmetrical heteroaryl thioethers via one-step formation of two C-S bonds under catalyst-, additive-, and solvent-free conditions. Mechanistic studies suggest that the crystal water in Na2S2O3·5H2O is crucial in generating the key thiol intermediates and byproduct NaHSO4, which then catalyzes the dehydrative substitution of alcohols with thiols to afford thioethers.

Efficient Generation of C–S Bonds via a By-Product-Promoted Selective Coupling of Alcohols, Organic Halides, and Thiourea

A metal- and base-free three-component coupling of alcohols, heteroaryl halides, and thiourea has been developed for direct and selective synthesis of heteroaryl thioethers. This method can be easily scaled up to the gram scale and extended to dialkyl thioethers, heteroaryl selenides, benzothiazoles, and some antimycobacterially-active thioethers. Mechanistic studies revealed that a by-product-promoted in situ C–O activation of alcohols to more reactive alkyl halides and slow release of the thiol and alkyl halide intermediates are the key to the high selectivity and success of the reaction. (Figure presented.).

Copper-Catalyzed Aerobic Formation of Unstable Sulfinyl Radicals for the Synthesis of Sulfinates and Thiosulfonates

Copper-catalyzed aerobic coupling of thiols and alcohols affords sulfinates and thiosulfonates. These products are assumed to form via sulfinyl radicals which are not commonly found in oxidative coupling reactions of thiols. A reaction mechanism involving sulfinyl radicals is proposed, and mass and electron paramagnetic resonance (EPR) experimental results are provided.

The effect of nitrogen atoms in the enantioselective oxidation of aryl or heteroaryl benzyl sulfides

Some aminophenyl benzyl sulfides or benzyl pyridyl sulfides were asymmetrically oxidized with tert-butyl hydroperoxide in the presence of a complex between titanium i-propoxide and (S, S)-hydrobenzoin, an oxidation system that works particularly well with

Hybrid molecules of estrone: New compounds with potential antibacterial, antifungal, and antiproliferative activities

New hybrid molecules of estrone were synthesized as compounds indicating promising biological activity (antibacterial, antimycobacterial, antifungal, and antiproliferative). The prepared molecules contained various heterocyclic units (pyridine, benzylsulf

Antimycobacterial Agents. 1. Thio Analogues of Purine

Thio analogues of purine, pyridine, and pyrimidine were prepared based on the initial activity screening of several analogues of these heterocycles against Mycobacterium tuberculosis (Mtb). Certain 6-thio-substituted purine analogues described herein showed moderate to good inhibitory activity. In particular, two purine analogues 9-(ethylcarboxymethyl)-6-(decylthio)-9H-purine (20) and 9-(ethylcarboxymethyl)-6-(dodecylthio)-9H-purine (21) exhibited MIC values of 1.56 and 0.78 μg/mL respectively against the Mtb H37Rv strain. N9-Substitution apparently enhances the antimycobacterial activity in the purine series described herein.

Synthetic Applications of N-N Linked Heterocycles. Part 12. The Preparation of 4-Alkylthio- and 4-Arylthio-pyridines by Regiospecific Attack of Thioalkoxide Ions on N-(4-Oxopyridin-1-yl)pyridinium Salts

Thiolate ions add regiospecifically to N-(4-oxopyridin-1-yl)pyridinium salts (2)-(7) to give in good to excellent yields only the 1,4-dihydropyridine adducts (8)-(13), regardless of whether or not the pyridone moiety carries substituents for sterically shielding the 2- and 6-positions of the pyridinium ring.The addition is believed to be thermodynamically controlled.Decomposition of the dihydro-adducts under free-radical conditions, or by pyrolysis, gives good yields of pyridin-4-yl thioethers (14) and (16) though the reaction failed with the 2-methyl adducts (9).An improved synthesis of 6-methyl-4-oxopyran-2-carboxylic acid is also described.