784-62-3

Usage

Purification Methods

This yellow solid is purified by passage through a silica gel column, eluting with *C6H6/Me6CO, evaporating and crystallising the residue from EtOH. The sulfoxide [65373-82-2] has m 133-135o, and the sulfone [22810-82-2] has m 136.5-137o (from EtOH). The dimethylhydrazone has m 111-113o (from BuOH). It forms easily hydrolysable salts. [Nakazumi et al. J Heterocycl Chem 21 193 1984, Chen et al. J Org Chem 51 3282 1986, Van Allen & Reynolds J Heterocycl Chem 8 807 1971, Beilstein 17 I 204, 17 III/IV 5420, 17/10 V 560.]

InChI:InChI=1/C15H10OS/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-10H

Upstream product

• 64448-06-2 (N-phenyliminovinylidene)triphenylphosphorane 
• 39860-52-1 2-(benzoylmercapto)benzoic acid 
• 70030-52-3 S-phenyl thiocinnamate 
• 75794-13-7 Ethyl 3-phenyl-3,3-bis(phenylthio)propionate 
• 34875-24-6 3-phenyl-3-(phenylthio)acrylic acid 
• 3019-19-0 tert-butyl phenyl sulfide 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 108-98-5 thiophenol 
• 92762-58-8 dithioflavylene 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 84144-48-9 (Z)-3-Phenyl-3-phenylsulfanyl-acryloyl chloride 
• 5962-00-5 2-phenyl-thiochroman-4-one 
• 32784-07-9 3-bromo-2-phenyl-thiochroman-4-one 
• 3739-97-7 (trimethylsilyl)methylenetriphenylphosphorane 

Downstream Products

• 119-80-2 2,2'-dithiobenzoic acid 
• 26824-02-2 1-(2-mercaptophenyl)ethan-1-one 
• 147-93-3 Thiosalicylic acid 
• 98-86-2 acetophenone 
• 92762-58-8 2,2'-diphenyl-[4,4']bithiochromenylidene 
• 13895-62-0 2-phenyl-4-((E)-2-phenyl-thiochromen-4-ylidene)-4H-oxazol-5-one 
• 22956-26-9 4-Methyl-2-phenylbenzo-1-thiopyrylium perchlorate 
• 98153-25-4 2-phenyl-4H-1-benzothiopyran-4-one-3-carboxylic acid 
• 93367-37-4 3-Hydroxymethyl-2-phenyl-4H-1-benzothiopyran-4-one 
• 93367-51-2 3-Chloromethyl-2-phenyl-4H-1-benzothiopyran-4-one 
• 15058-08-9 4-(dicyanomethylene)-4H-thioflaven-4-one 
• 33928-00-6 3-methyl-2-phenyl-4H-thiochromen-4-one 
• 112763-70-9 4'-Hydroxy-2,2'-diphenyl-4'H-[3,4']bithiochromenyl-4-one 
• 35813-96-8 2-phenyl-4H-benzothiopyran 

Relevant academic research and scientific papers

Catalytic Enantioselective Synthesis of 3,4-Unsubstituted Thiochromenes through Sulfa-Michael/Julia-Kocienski Olefination Cascade Reaction

A highly enantioselective cascade sulfa-Michael/Julia-Kocienski olefination reaction between 2-mercaptobenzaldehydes and β-substituted vinyl PT-sulfones has been realized for the synthesis of 3,4-unsubstituted 2H-thiochromenes. This reaction, catalyzed by diphenylprolinol TMS ether, proceeds through an aromatic iminium intermediate and furnishes a wide range of 2-substiuted 2H-thiochromenes with excellent enantioselectivities (up to 99:1 er).

Copper-catalyzed domino synthesis of multi-substituted benzo[: B] thiophene through radical cyclization using xanthate as a sulfur surrogate

The Cu-catalyzed domino synthesis of multi-substituted benzo[b]thiophene through radical cyclization of 2-iodophenyl ketones was developed using xanthate as a sulfur surrogate. This method was extended to obtain tetracyclic Lupinalbin analogues through do

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

Conjugate addition of grignard reagents to thiochromones catalyzed by copper salts: A unified approach to both 2-alkylthiochroman-4-one and thioflavanone

Grignard reagents undergo conjugate addition to thiochromones catalyzed by copper salts to afford 2-substituted-thiochroman-4-ones, both 2-alkylthiochroman-4-ones and thioflavanones (2-arylthiochroman-4-ones), in good yields with trimethylsilyl chloride (TMSCl) as an additive. The best yields of 1,4-adducts can be attained with CuCN-2LiCl as the copper source. Excellent yields of 2-alkyl-substituted thiochroman-4-ones and thioflavanones (2-aryl substituted) are attained with a broad range of Grignard reagents. This approach works well with both alkyl and aromatic Grignard reagents, thus providing a unified synthetic approach to privileged 2-substituted thiochroman-4-ones and a potential valuable precursor for further synthetic applications towards many pharmaceutically active molecules. The use of commercially available and/or readily prepared Grignard reagents will expedite the synthesis of a large library of both 2-alkyl substituted thiochroman-4-ones and thioflavanones for additional synthetic applications.

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.

Stereoselective Synthesis of Z-Vinyl Selenides Through the Reaction of Sodium Selenide with Organic Halides and Alkynes

A practical synthetic approach to the stereoselective synthesis of Z-vinyl selenides is described through the reaction of sodium selenide with organic halides, followed by the addition to alkynes. The reaction conditions were also successfully applied to

Synthesis of Enones and Enals via Dehydrogenation of Saturated Ketones and Aldehydes

A general, efficient and economic palladium-catalyzed dehydrogenation to form enones or enals has been developed. The approach possesses extremely broad substrate scope including various linear or cyclic saturated ketones and aldehydes. The protocol is ligand-free, and molecular oxygen is used as the sole clean oxidant in the reaction. Due to mild reaction conditions, good functional group compatibility, and versatile utilities of enones and enals, the method can be applied in the late-stage synthesis of natural products, pharmaceuticals and fine chemicals. (Figure presented.).

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.