26524-91-4

Upstream product

• 3528-17-4 2,3-dihydro-4H-[1]benzothiopyran-4-one 
• 127-65-1 chloroamine-T 

Downstream Products

• 74695-69-5 5,10-Dioxo-5,10-dihydro-10λ⁴-thia-4a-aza-benzo[b]fluorene-11-carboxylic acid phenylamide 
• 3844-31-3 trans-thioindigo 

Relevant academic research and scientific papers

Chemo- and diastereoselectivity in the dimethyldioxirane oxidation of 2,3-dihydro-4H-1-benzothiopyran-4-ones and 4H-1-benzothiopyran-4-ones. Unusual reactivity of 4H-1-benzothiopyran-4-one 1-oxides1

The oxidation of the 1-thiochromanones 1-3 by dimethyldioxirane (DMD) produced the corresponding sulfoxides 4-6 or sulfones 7-9; their relative amounts depended on the amount of oxidant used. A low diastereoselectivity was observed in the sulfoxidation of

A mild, efficient and selective oxidation of sulfides to sulfoxides

Several titanium derivatives supported on silica have been investigated as catalysts in the sulfide→sulfoxide oxidation; the supported titanium/tartaric acid catalyst is highly suited to reactions carried out with H2O2, leading to high yields and high sulfoxide/sulfone selectivities, while small asymmetric inductions (up to 13%) are observed.

Chloroperoxidase-catalyzed asymmetric synthesis of a series of aromatic cyclic sulfoxides

The chloroperoxidase (CPO) catalyzed oxidation of a series of rigid aromatic sulfides of well-defined geometry has been studied by the use of enantioselective gas chromatography for the determination of product composition and sulfoxide enantiomeric excess. The almost planar 1-thiaindane was found to be an excellent substrate, giving a quantitative yield of the (-)-(R)-1-oxide in 99% e.e. The sterically more demanding next higher homolog with a six-membered heterocyclic ring, 1-thiatetrahydronaphthalene (1-thiochroman), also gave a sulfoxide in high e.e. (≥ 96%) but in a much lower yield, indicating a preserved stereorecognition ability but a lower turnover rate. A carbonyl group in the 4-position (1-thiochroman-4-one) had no further effect on the CPO-mediated sulfoxidation. Enantio-selectivity was lost for the symmetric disulfide, 1,3-benzodithiol, indicating an equal accessibility of the Fe=O complex towards both sulfur atoms and an active site centred above the heme-iron atom. In all cases with pronounced enantioselectivity the reaction gave the (R)-sulfoxide as observed previously with alkyl aryl sulfides. A change of oxygen source from hydrogen peroxide to t-butyl hydroperoxide and a longer reaction time gave a higher chemical but a lower optical yield, most likely due to an increased competition by the uncatalyzed oxidation reaction in this case.

Conversions of Thiochroman-4-ones into 1,2-Benzothiazepine, Benzothiophen, and 1,2-Benzisothiazole Systems via Sulphimide Intermediates

Reaction of thiochroman-4-ones (1a-g) with chloramine-T gave the corresponding N-tosylsulphimides (2a-g) and sulphoxides (5a-g).The N-tosylsulphimides (2a-d), on reaction with triethylamine in chloroform, gave 2-tosyl-2,3-dihydro-1,2-benzothiazepin-5(4H)-

SULFILIMINES IN ORGANIC SYNTHESES: NEW ENTRIES INTO TETRAHYDRO-1,2-BENZOTHIAZEPINE AND 1,2-BENZISOTHIAZOLE SYSTEMS

Novel ring transformations of thiochroman-4-ones and benzothiophen-3(2H)-ones to tetrahydro-1,2-benzothiazepin-5-ones and 1,2-benzisothiazoles via sulfilimine intermediates are described.