90922-18-2

Upstream product

• 35756-39-9 4-(phenylthio)butanenitrile 
• 5535-48-8 PVS 
• 71823-67-1 (E)-1-([1,1'-biphenyl]-4-yl)but-2-en-1-one 
• 75-05-8 acetonitrile 
• 873-55-2 sodium benzenesulfonate 
• 108-98-5 thiophenol 
• 66003-76-7 Diphenyliodonium triflate 
• 126761-11-3 iodo-(3-cyanopropyl)zinc 

Relevant academic research and scientific papers

Copper-Catalyzed Radical Cross-Coupling of Oxime Esters and Sulfinates for Synthesis of Cyanoalkylated Sulfones

Sulfones and alkylnitriles play a significant role in both organic and medicinal chemistry, as versatile synthetic building blocks and privileged pharmacophores in many natural products and bioactive compounds. Herein, a room-temperature, copper-catalyzed radical cross-coupling of redox-active cycloketone oxime esters and sulfinate salts is described for the first time. Key to the success of this process involves catalytic generation of a cyclic iminyl radical and ensuing ring-opening C?C bond cleavage. The resultant cyanoalkyl radical is then engaged in cross-coupling with nucleophilic sulfinate to form cyanoalkylated sulfones.

One-pot synthesis of aryl sulfones from organometallic reagents and iodonium salts

A transition-metal-free arylation of lithium, magnesium, and zinc sulfinates with diaryliodonium salts is described. The sulfinic acid salts were prepared from the reaction of the corresponding organometallic reagents and sulfur dioxide. Combination of the three single steps (preparation of the organometallic compound, sulfinate formation, and arylation) leads to a one-pot sequence for the synthesis of aryl sulfones from simple starting materials. The chemoselectivity of unsymmetrical diaryliodonium salts has been investigated. Potential and limitations of this method will be discussed.

Electrocatalytic reactions: anion radical cyclobutanation reactions and electrogenerated base reactions

Intermolecular anion radical [2+2] cyclobutanation reactions have been observed between vinyl sulfones and vinyl/propenyl ketones. The products are novel and formed electrocatalytically, although yields are at best modest (11-45%). Competing mechanisms are discussed. Additionally, the electrochemical reduction of vinyl alkyl sulfones in acetonitrile leads to near quantitative formation of cyanomethylation product cyano-sulfones. The single step approach has electrocatalytic factors in excess of thirty.

THIOREDOXIN AND THIOREDOXIN REDUCTASE INHIBITORS

The present invention relates to sulfone derivatives and to their use as modulators of the thioredoxin/thioredoxin reductase redox system, including for the treatment and/or prevention of pathophysiological conditions mediated by thioredoxin/thioredoxin reductase, such as cancer, HIV/ AIDS, Alzheimer's disease, rheumatoid arthritis, and skin disorders. Also provided are pharmaceutical compositions comprising the inventive sulfones.