6586-36-3

Upstream product

• 66724-23-0 2-(4'-chlorophenyl)-4H-1-benzothiopyran-4-one 
• 1026511-99-8 3-(4-Chloro-phenyl)-3-phenylsulfanyl-propionyl chloride 
• 2142-70-3 2-iodoacetophenone 
• 108-98-5 thiophenol 
• 1615-02-7 p-chlorocinnamic acid 
• 6602-15-9 3-(4-chlorophenyl)-3-(phenylmercapto)propanoic acid 
• 6048-06-2 ethyl-p-chlorocinnamate 
• 104-88-1 4-chlorobenzaldehyde 
• 147-93-3 Thiosalicylic acid 

Downstream Products

• 66724-23-0 2-(4'-chlorophenyl)-4H-1-benzothiopyran-4-one 
• 77261-93-9 2-(4-chlorophenyl)-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-one 

Relevant academic research and scientific papers

Visible Light Mediated Photocatalyst Free C-S Cross Coupling: Domino Synthesis of Thiochromane Derivatives via Photoinduced Electron Transfer

An efficient visible light mediated photocatalyst free C-S cross-coupling reaction has been developed for the synthesis of thiochromane derivatives through photoinduced electron transfer (PET). This methodology was further utilized for the synthesis of thiochroman-4-ol through intermolecular three-component cross-coupling reaction. The reaction proceeds via C-S bond formation through EDA complex/thioester cleavage/inter-or intramolecular sulfa-Michael addition followed by aldol reaction sequence. The EDA complex formation between aryl iodides and xanthate has been substantiated using spectroscopic experiments and DFT calculations.

Copper-Catalyzed One-Pot Synthesis of 2-Arylthiochromenones: An in Situ Recycle of Waste Byproduct as Useful Reagent

Copper-catalyzed one-pot synthesis of various 2-arylthiochromenones is developed using xanthate as an odorless sulfur source from easily acquirable 2′-halochalcones. This methodology demonstrates that the cross-coupled product thiochromanone synthesized from 2′-halochalcones (upstream reaction) is oxidized to thiochromenone (downstream reaction) in the same pot using waste byproduct (KI) of the first step as powerful oxidant molecular iodine (I2). This one-pot synthesis has been further extended for the synthesis of 3,3′-methylenebisthioflavone using dimethyl sulfoxide (DMSO) as solvent and methylene source.

Synthesis and evaluation of thiochroman-4-one derivatives as potential leishmanicidal agents

The S-containing heterocyclic compounds benzothiopyrans or thiochromones stand out as having promising biological activities due to their structural relationship with chromones (benzopyrans), which are widely known as privileged scaffolds in medicinal chemistry. In this work, we report the synthesis of 35 thiochromone derivatives and the in vitro antileishmanial and cytotoxic activities. Compounds were tested against intracellular amastigotes of Leishmania panamensis and cytotoxic activity against human monocytes (U-937 ATCC CRL-1593.2). Compounds bearing a vinyl sulfone moiety, 4h, 4i, 4j, 4k, 4l and 4m, displayed the highest antileishmanial activity, with EC50 values lower than 10 μM and an index of selectivity over 100 for compounds 4j and 4l. When the double bond or the sulfone moiety was removed, the activity decreased. Our results show that thiochromones bearing a vinyl sulfone moiety are endowed with high antileishmanial activity and low cytotoxicity.

Copper-Catalyzed Domino Synthesis of 2-Arylthiochromanones through Concomitant C-S Bond Formations Using Xanthate as Sulfur Source

An efficient domino process for the synthesis of thioflavanones has been described using a copper catalyst without addition of any external ligand. A variety of thioflavanones have been synthesized from easily accessible 2′-iodochalcones or 2′-bromochalco

Synthesis of flavanones, azaflavanones, and thioflavanones catalyzed by PMA-SiO2 as a mild, efficient, and reusable catalyst

Cyclization of a variety of chalcones to flavanones catalyzed by 1 mol% phosphomolybdic acid (PMA) supported on silica as a mild, efficient, and reusable catalyst was carried out in high yields. PMA-SiO2 is an efficient, inexpensive, and green catalyst which gave high conversion yields and could be recycled up to three times without significant loss in activity. Springer-Verlag 2011.

Benzodiazepine analogues. Part 8. Trimethylsilyl azide mediated Schmidt rearrangement of thioflavanone and thiochromanone precursors

The synthesis and Schmidt rearrangement of a series of thioflavanone analogues to benzothiazepinone derivatives is described.