- Synthesis of sodium allyl sulfonate in an aqueous medium by micellar catalysis with methoxy polyethylene glycol methacrylates
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Micellar catalysis with various polyoxyethylated compounds was used to synthesize sodium allyl sulfonate by the reaction of allyl chloride with an aqueous solution of sodium sulfite. It was shown that methoxy polyethylene glycol methacrylates and water soluble polymers based on these compounds are surfactants and can be used to intensify the synthesis of sodium allyl sulfonate, which is of interest in the case of its subsequent application to obtain copolymers with methoxy polyethylene glycol methacrylates.
- Orekhov,Kazantsev,Sivokhin,Khokhlova
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- Ring closing metathesis and metal-catalyzed cyclopropanation for the preparation of sultone derivatives
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Ring closing metathesis (RCM) using Grubbs catalyst 2nd generation as a catalyst was applied to prepare series of novel unsaturated sultones with high yields. Many attempts, were applied for the cyclopropanation of the allylic sultones by Simmon-smith cyclopropanation using diethyl zinc/diiodomethane or Zn-Cu/diiodomethane but in each case the corresponding cyclic adduct was not formed. A novel palladium or preferably rhodium-catalyzed cyclopropanation of unsaturated sultones with ethyl diazoacetate was achieved by the transition metal-catalyzed transfer of a CH-CO2Et unit. The reaction was applied by a portion-wise addition of ethyl diazoacetate over 6h to a mixture of the sultones and palladium(II) acetate or rhodium(II) acetate dimer under low temperature (0-20 o C). The desired products of the cyclopropanation were achieved in each case, as a single diastereomer with 33- 37% yield in the allylic sultones and 10% for vinylic sultone.
- Ali, Korany A.,Metz, Peter
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- Synthesis method of sodium allysulfonate
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The invention discloses a synthesis method of sodium allysulfonate. The synthesis method comprises the following steps: adding a phase transfer catalyst and a polymerization inhibitor into a sodium pyrosulfite solution, uniformly stirring and mixing, thus obtaining a sodium pyrosulfite mixed solution, and simultaneously introducing the sodium metabisulfite mixed solution, a sodium hydroxide solution and allyl chloride into a reactor to react, thus obtaining a target product. According to the synthesis method, by changing the feeding sequence of the raw materials, the raw materials anticipatingin the reaction simultaneously enter the reactor to react, and the phase transfer catalyst and polymerization inhibitor are added, so that the side reaction can be greatly reduced, the selectivity and the conversion rate of the reaction can be improved, and the yield of products can be improved; and compared with a traditional method, the method does not need the subsequent steps of dehydration,active carbon discoloration, impurity removal and the like, the subsequent treatment steps are simple, the production cost is reduced, the production efficiency is improved, and the synthetic method of the sodium allysulfonate is more suitable for the industrialized production.
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Paragraph 0023-0034
(2019/02/04)
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- 6-MEMBERED URACIL ISOSTERES
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Provided herein are dUTPase inhibitors, compositions comprising such compounds and methods of using such compounds and compositions.
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Paragraph 0779
(2018/06/12)
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- HYDANTOIN CONTAINING DEOXYURIDINE TRIPHOSPHATASE INHIBITORS
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Provided herein are dUTPase inhibitors, compositions comprising such compounds and methods of using such compounds and compositions.
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Paragraph 0992
(2018/06/12)
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- Olefination with Sulfonyl Halides and Esters: E-Selective Synthesis of Alkenes from Semistabilized Carbanion Precursors
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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.
- Górski, Bartosz,Basiak, Dariusz,Talko, Alicja,Basak, Tymoteusz,Mazurek, Tomasz,Barbasiewicz, Micha?
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supporting information
p. 1774 - 1784
(2018/04/27)
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- Solvent-free, metal-free, aza-prins cyclization: Unprecedented access to δ-sultams
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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
- Clarisse, Damien,Pelotier, Béatrice,Fache, Fabienne
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supporting information
p. 857 - 860
(2013/02/25)
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- Methods and compositions for treating amyloid-related diseases
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Methods, compounds, pharmaceutical compositions and kits are described for treating or preventing amyloid-related disease.
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Page/Page column 173-174
(2010/11/24)
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- 1,3-Dipolar cycloaddition reactions of nitrones to prop-1-ene-1,3-sultone
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The reaction of prop-1-ene-1,3-sultone (1) with a variety of nitrones 2 afforded novel [3+2] cycloaddition products 3, 4, and 5 in good yield. Excellent regio- and stereoselectivity were achieved in the cycloaddition reaction with phenylnitrones.
- Tian, Li,Xu, Guo-Yan,Ye, Yong,Liu, Lun-Zu
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p. 1329 - 1334
(2007/10/03)
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- 1,3-Dipolar Cycloaddition Reactions of Nitrile Oxides to Prop-1-ene-1,3-sultone
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The reaction of prop-1-ene-1,3-sultone 1 with a variety of nitrile oxides 3 afforded novel [3+2] cycloaddition products 4 in good yield. The cycloaddition reaction achieved excellent regioselectivity.
- Tian, Li,Xu, Guo-Yan,Ye, Yong,Liu, Lun-Zu
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p. 1071 - 1074
(2007/10/03)
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- Synthesis and Diels-Alder reactions of prop-1-ene-1,3-sultone, and chemical transformations of the Diels-Alder adducts
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A reliable and novel synthetic route for the preparation of prop-1-ene- 1,3-sultone (1) has been developed. An overall yield of 34% could be achieved for this five-step synthesis. The Diels-Alder reactions of 1 with a variety of dienes were investigated for the first time and achieved with good chemical yield and excellent endo-selectivity. The subsequent transformations of the Diels-Alder cycloadducts were also explored.
- Jiang, La Sheng,Chan, Wing Hong,Lee, Albert W. M.
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p. 2245 - 2262
(2007/10/03)
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- Synthesis and Diels-Alder reactions of α,β-unsaturated γ-sultone
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An efficient synthesis of prop-1-ene 1,3-sultone 1 and its Diels-Alder reactions are reported; ring-opening reactions of the cycloadducts with nucleophiles and transformations to the sultams were also investigated.
- Lee, Albert W. M.,Chan,Jiang,Poon
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p. 611 - 612
(2007/10/03)
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- Mechanisms of hydrolysis and related nucleophilic displacement reactions of alkanesulfonyl chlorides: pH dependence and the mechanism of hydration of sulfenes
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pH-rate profiles, primary kinetic isotope effects, deuterium substitution patterns, and pH-product ratios in the presence of added nucleophiles provide evidence for the following overlapping set of mechanisms for the hydrolysis of methanesulfonyl chloride (1) (in 0.1 M KCl at 25 °C): (a) pH ≤ 1-6.7, reaction with water by direct nucleophilic attack on the sulfonyl chloride; (b) pH ≥ 6.7-11.8, rate-determining attack by hydroxide anion to form sulfene (2), which is then trapped by water in a fast step; and (c) pH ≥ 11.8, sulfene formation and sulfene trapping by hydroxide anion; careful inspection showed no sign of sulfene formation in the reaction with water or of direct displacement by hydroxide anion. This pattern, with appropriate variations in the values of pHi (the pH at which two competing mechanisms have the same rate), is apparently general for simple alkanesulfonyl chlorides having at least one hydrogen on the carbon bearing the sulfonyl group. Azide and acetate anions react with 1 below pHi for 1 (6.7) by direct nucleophilic substitution at the sulfur, but above pHi by trapping of the sulfene. 2-Chlorophenoxide anion reacts with 1 below pH 6.7 by both (a) direct displacement to form the ester and (b) elimination to form the sulfene. Above pH 6.7, sulfene is formed from the sulfonyl chloride by reaction with either 2-chlorophenoxide or hydroxide ion; this is followed by trapping of the sulfene with 2-chlorophenoxide, water, or hydroxide. The possibility of the 2-chlorophenoxide anion acting as a general base promoting the reaction of water with either 1 and 2 was examined, but no sign of either process was detected.
- King,Lam,Skonieczny
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p. 1743 - 1749
(2007/10/02)
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