893-10-7

Upstream product

• 64448-06-2 (N-phenyliminovinylidene)triphenylphosphorane 
• 145702-37-0 2-(4-Methoxy-benzoylsulfanyl)-benzoic acid 
• 3739-97-7 (trimethylsilyl)methylenetriphenylphosphorane 
• 405271-47-8 C₂₁H₂₆O₄SSi 
• 1314533-39-5 C₁₆H₁₄O₃S 
• 1198288-47-9 C₁₆H₁₄O₃S 
• 26824-02-2 1-(2-mercaptophenyl)ethan-1-one 
• 1135136-54-7 2-(4-methoxyphenyl)thiochroman-4-one 
• 768-60-5 4-methoxyphenylacetylen 
• 108-86-1 bromobenzene 
• 2905-25-1 o-bromobenzenesulfonyl chloride 
• 13939-06-5 molybdenum hexacarbonyl 
• 108-98-5 thiophenol 
• 2881-83-6 ethyl 4-methoxybenzoylacetate 

Downstream Products

• 96156-22-8 2-(4-Methoxy-phenyl)-1,1-dioxo-1H-1λ⁶-thiochromen-4-one 
• 120229-41-6 3,4-Dihydro-2-(4-methoxyphenyl)-2H-1-benzothiopyran 
• 93367-31-8 2-(3,5-Bis-chloromethyl-4-methoxy-phenyl)-3-chloromethyl-thiochromen-4-one 

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.

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.

Second near-infrared window emitting pentamethine cyanine fluorescent dyes, and preparation method and application thereof

The invention belong to the technical field of biomaterials, and concretely relates to second near-infrared window emitting pentamethine cyanine fluorescent dyes, and a preparation method and an application thereof. The pentamethine cyanine fluorescent dyes have a large molar extinction coefficient, a long absorption and emission wavelength and a wide adjustable wavelength range, is not prone to be solvatochromic in a polar solvent, and has better quenching resistance and higher fluorescence intensity in water than existing second near-infrared window emitting heptamethine cyanine fluorescentdyes, so high-resolution imaging of mouse lymph and detection of the acidity of the stomach with deep penetration can be achieved.

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.

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

Unified Approach to (Thio)chromenones via One-Pot Friedel-Crafts Acylation/Cyclization: Distinctive Mechanistic Pathways of β-Chlorovinyl Ketones

A facile synthetic method to chromenones and thiochromenones has been developed using a one-pot Friedel-Crafts acylation of alkynes with suitably substituted benzoyl chlorides. This unified approach to (thio)chromenones is readily applicable to aryl- and alkylalkynes where the stereochemically well-defined β-chlorovinyl ketone intermediates undergo distinctively different cyclization pathways. The ready availability of both starting materials, alkynes and benzoyl chlorides, coupled with the experimental simplicity makes the current synthetic method to (thio)chromenones fast, efficient, and practical.

Two-Component Assembly of Thiochroman-4-ones and Tetrahydrothiopyran-4-ones Using a Rhodium-Catalyzed Alkyne Hydroacylation/Thio-Conjugate-Addition Sequence

β′-Thio-substituted-enones, assembled from the combination of β-tert-butylthio-substituted aldehydes and alkynes, using rhodium catalysis, are shown to smoothly undergo in situ intramolecular S-conjugate addition to deliver a range of S-heterocycles in a one-pot process. Aryl, alkenyl, and alkyl aldehydes can all be employed, to provide thiochroman-4-ones, hexahydro-4H-thiochromen-4-ones, and tetrahydrothiopyran-4-ones, respectively. A variety of in situ oxidations are also performed, allowing access to S,S-dioxide derivatives, as well as unsaturated variants.

Practical and versatile synthesis of thioflavones from 2-bromobenzoyl chlorides

A practical and versatile synthesis of thioflavones from 2-bromobenzoyl chlorides as potent drug candidates, including derivatives with chloro, methyl, or methoxy substituents on the condensed benzene ring was reported. 4,6-Pyrimidyl di(2-halobenzoates)were readily prepared by acylation of 2 equiv of 1 with 4,6-dihydroxypyrimidine in the presence of 2 equiv of triethylamine in methylene chloride at room temperature. After evaporating methylene chloride, the mixture was dissolved in anhydrous THF and triethylamine hydrochloride was filtered off. The condensed residue was purified by short pathway silica gel column chromatography or recrystallization in 75% EtOAc/n-hexane to give 2 in 85-94% yields. Successful synthesis of 2 equiv of 1-(2-bromophenyl)-3-(hetero)aryl-2-propyn-1-ones was accomplished by reacting 1 equiv of 2 with 2 equiv of (hetero)arylethynylmagnesium bromides. Benzothiopyran ring formation was achieved via the 1,4-addition of hydrosulfide anion and one-pot sequence of bromide substitution. The reaction worked well with electron-withdrawing substituents, such as 7-chloro groups, and electrondonating substituents, such as 7-methyland 6-methoxy groups, in the condensed benzene rings.

Iodine-catalyzed intramolecular oxidative thiolation of vinylic carbon-hydrogen bonds via tandem iodocyclization and dehydroiodination: Construction of 2-methylene-3-thiophenones

A metal-free vinylic carbon-hydrogen bond thiolation has been developed. Under the catalysis of iodine (10 mol%), the cyclization of α-alkenoyl ketene dithioacetals afforded a broad range of polyfunctionalized 2-methylene-3-thiophenones in good selectivity with moderate to excellent yields via tandem iodocyclization and dehydroiodination. The synthetic strategy can also be extended to the cyclization of ortho-methylthiophenyl vinyl ketones leading to 2-methylene-3-benzothiophenones.