14418-84-9Relevant articles and documents
Remote Site-Specific Radical Alkynylation of Unactivated C-H Bonds
Wang, Lin,Xia, Yong,Bergander, Klaus,Studer, Armido
, p. 5817 - 5820 (2018)
A method for remote radical C-H alkynylation at unactivated sites is reported. C-H functionalization proceeds via 1,5-hydrogen atom transfer (HAT) to amidyl radicals that are generated via an addition/fragmentation reaction. The readily installed N-allylsulfonyl moiety is used as a precursor of the N-centered radical. Unactivated secondary and tertiary as well as selected primary C-H bonds can be functionalized by this method.
Solvent-free, metal-free, aza-prins cyclization: Unprecedented access to δ-sultams
Clarisse, Damien,Pelotier, Béatrice,Fache, Fabienne
, p. 857 - 860 (2013)
Aza-Prins and the pauper: Aza-Prins cyclization between γ,δ-unsaturated tosylamines and aldehydes was successfully performed under solvent-free and metal-free conditions. When applied to β,γ-unsaturated sulfonamides, the corresponding δ-sultams were isolated in good yields (see scheme). This approach constitutes a new route to cyclic sulfonamides. Copyright
3H-1,2-benzoxathiepine 2,2-dioxides: a new class of isoform-selective carbonic anhydrase inhibitors
Pustenko, Aleksandrs,Stepanovs, Dmitrijs,?alubovskis, Raivis,Vullo, Daniela,Kazaks, Andris,Leitans, Janis,Tars, Kaspars,Supuran, Claudiu T.
, p. 767 - 775 (2017)
A new chemotype with carbonic anhydrase (CA, EC 4.2.1.1) inhibitory action has been discovered, the homo-sulfocoumarins (3H-1,2-benzoxathiepine 2,2-dioxides) which have been designed considering the (sulfo)coumarins as lead molecules. An original synthetic strategy of a panel of such derivatives led to compounds with a unique inhibitory profile and very high selectivity for the inhibition of the tumour associated (CA IX/XII) over the cytosolic (CA I/II) isoforms. Although the CA inhibition mechanism with these new compounds is unknown for the moment, we hypothesize that it may be similar to that of the sulfocoumarins, i.e. hydrolysis to the corresponding sulfonic acids which thereafter anchor to the zinc-coordinated water molecule within the enzyme active site.
Process for preparing 2 - (methylsulfonyl) - ethylene oxide and derivatives thereof
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Paragraph 0038-0040; 0051-0053, (2021/09/29)
The invention relates to 2 - (methylsulfonyl) - ethylene oxide and a preparation method thereof, belonging to the technical field of synthesis of ethylene oxide derivatives, and the method comprises the following steps: raw materials are vinyl methyl sulfone or allyl methyl sulfone 1:2:4 or methylallyl sulfonic acid ester. @timetimepieces are added dropwise to m-chloroperoxybenzoic acid by dropwise adding time of 30 min, 25 min, 10 min, heating reflux 15 - 30h and cooling to room temperature filtration. When the starting material is a vinyl methyl sulfone, the product is 2 - (methylsulfonyl) - ethylene oxide. When the starting material is allyl methyl sulfone, the product is methyl -2 and 3 - propylene oxide sulfonate. When the starting material is methylallyl sulfonate, the product is methyl -2 and 3 - epoxypropane sulfonate. The molar ratio of the raw material and the m-chloroperbenzoic acid is 1: (1.8 - 2.4). The preparation method is simple and high in yield.
Olefination with Sulfonyl Halides and Esters: E-Selective Synthesis of Alkenes from Semistabilized Carbanion Precursors
Górski, Bartosz,Basiak, Dariusz,Talko, Alicja,Basak, Tymoteusz,Mazurek, Tomasz,Barbasiewicz, Micha?
supporting information, p. 1774 - 1784 (2018/04/27)
Carbanions of sulfonyl halides and activated sulfonates add to carbonyl compounds, and so-formed aldol-type adducts spontaneously fragment into olefins. This transformation mimics the one-pot Julia olefination with (hetero)aryl sulfones, but the mechanism of fragmentation involves a four-membered intermediate, typical for reactivity of phosphorus reagents. Moreover, in contrast to the reactions of sulfones, sulfonates of fluorinated alcohols (TFE and HFI) produce byproducts that are easily removed during workup. In our report, we focus on reactions of unstabilized and semistabilized carbanion precursors: alkylsulfonates, and allyl- and benzylsulfonates, respectively. In particular for semistabilized systems, olefins were synthesized as predominant E isomers in good yields. The presented studies reveal that optimal reaction conditions, including the type of base and alcohol groups of the sulfonates, are different depending on stabilization of the carbanion precursors and structure of the carbonyl substrates. The practical synthetic guide is supplemented with a discussion of the mechanism, based on reactivity studies of intermediates and identification of side-products.
