66724-23-0

Upstream product

• 3739-97-7 (trimethylsilyl)methylenetriphenylphosphorane 
• 405271-44-5 C₂₀H₂₃ClO₃SSi 
• 147-93-3 Thiosalicylic acid 
• 4892-02-8 Methyl thiosalicylate 
• 637-87-6 1-Chloro-4-iodobenzene 
• 491-39-4 thiochromen-4-one 
• 64448-06-2 (N-phenyliminovinylidene)triphenylphosphorane 
• 145702-36-9 2-(4-Chloro-benzoylsulfanyl)-benzoic acid 
• 108-86-1 bromobenzene 
• 873-73-4 4-n-chlorophenylacetylene 
• 2905-25-1 o-bromobenzenesulfonyl chloride 
• 13939-06-5 molybdenum hexacarbonyl 
• 89-98-5 2-chloro-benzaldehyde 
• 192573-58-3 3-(4-chlorophenyl)-1-(2-chlorophenyl)propyn-1-one 

Downstream Products

• 6586-36-3 2-(4-chlorophenyl)-2,3-dihydro-4H-1-benzopyran-4-one 
• 78317-71-2 2-(4-Chlorphenyl)-3,4-dihydro-2H-1-benzothiopyran 

Relevant academic research and scientific papers

Nickel-Catalyzed One-Pot Carbonylative Synthesis of 2-Mono- And 2,3-Disubstituted Thiochromenones from 2-Bromobenzenesulfonyl Chlorides and Alkynes

A nickel-catalyzed one-pot carbonylation reaction of 2-bromobenzenesulfonyl chlorides with alkynes for the synthesis of thiochromenones has been established. Both terminal and internal alkynes were suitable substrates in this carbonylative transformation, and a broad range of 2-mono- and 2,3-disubstituted thiochromenone products were obtained in moderate to good yields with quite high functional group compatibility. Notably, this procedure presents the first example of nickel-catalyzed carbonylative synthesis of thiochromenones with 2-bromobenzenesulfonyl chlorides as a promising sulfur precursor.

Elemental chalcogen (Se, S) in PEG-400 to the synthesis of seleno- And thioflavones from 2-chlorophenyl ethynyl ketone and nucleophilic species of chalcogen

An alternative green method was developed for the synthesis of thio- and selenoflavones by the ring closure of 2-chlorophenyl ethynyl ketone with NaHY (Y = S, Se). These nucleophilic chalcogen species were generated in situ using NaBH4 to reduc

Competitive cascade cyclization of 2′-tosyloxychalcones: An easy access to thioflavones and thioaurones

A new and efficient approach for the synthesis of thioflavones and thioaurones by competitive cascade cyclization of 2′-tosyloxychalcones has been developed. 2′-Tosyloxychalcones were smoothly converted into thioflavones and thioaurones by incorporation of sulfur atom using elemental sulfur and triethylamine in DMSO with good yields. The advantages of the methodology are the formation of both thioflavones and thioaurones in a single step. Easily accessible substrates, mild reaction conditions and compatibility with a broad range of functional groups make this protocol clean and inexpensive.

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.

Carbonylative Synthesis of Thiochromenones via Palladium-Catalyzed tert -Butyl Isocyanide Insertion

A flexible and efficient carbonylative synthesis of thiochromenones from the commercially available materials by utilizing tert -butyl isocyanide as carbonyl source has been developed. This methodology efficiently constructs thiochromenones in moderate to excellent yields with the advantages of wide range of substrates and being applicable to library synthesis.

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.

Transition-Metal-Free One-Pot Tandem Synthesis of 4-Quinolone and 4 H -Thiochromen-4-one Derivatives Through Sequential Nucleophilic Addition-Elimination-S N Ar Reaction

4-Quinolone and 4 H -thiochromen-4-one derivatives are readily synthesized in a tandem one-pot manner in good to excellent yields. Starting from (Z)-β-chlorovinyl ketones, an intermolecular nucleo-philic addition of amines or sodium hydrogen sulfide to (Z

The involvement of the trisulfur radical anion in electron-catalyzed sulfur insertion reactions: Facile synthesis of benzothiazine derivatives under transition metal-free conditions

An efficient and practical synthesis of benzothiazine by K2S initiated sulfur insertion reaction with enaminones via electron catalysis is developed. This protocol provides a new, environment-friendly and simple strategy to construct benzothiaz

Transition metal free intramolecular S-arylation: One-pot synthesis of thiochromen-4-ones

A convenient one-pot method for the synthesis of thiochromen-4-ones by the condensation of 2′-haloacetophenone and dithioesters at room temperature in the presence of NaH in DMF in moderate to good yields has been developed. The method involves unusual intramolecular S-arylation. The reaction is operationally facile, readily scalable and offers rapid entry into substituted chromene-4-ones.

Lewis acid-triggered selective zincation of chromones, quinolones, and thiochromones: Application to the preparation of natural flavones and isoflavones

A Lewis acid-triggered zincation allows the regioselective metalation of various chromones and quinolones. In the absence of MgCl2, a C(3) zincation is observed, whereas in the presence of MgCl2 or a related Lewis acid, C(2) zincation occurs. Applications to a natural flavone, isoflavone, and quinolone are shown.