24599-52-8Relevant academic research and scientific papers
Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction
Isshiki, Ryota,Kurosawa, Miki B.,Muto, Kei,Yamaguchi, Junichiro
, p. 10333 - 10340 (2021/07/21)
A Ni-catalyzed aryl sulfide synthesis through an aryl exchange reaction between aryl sulfides and a variety of aryl electrophiles was developed. By using 2-pyridyl sulfide as a sulfide donor, this reaction achieved the synthesis of aryl sulfides without using odorous and toxic thiols. The use of a Ni/dcypt catalyst capable of cleaving and forming aryl-S bonds was important for the aryl exchange reaction between 2-pyridyl sulfides and aryl electrophiles, which include aromatic esters, arenol derivatives, and aryl halides. Mechanistic studies revealed that Ni/dcypt can simultaneously undergo oxidative additions of aryl sulfides and aromatic esters, followed by ligand exchange between the generated aryl-Ni-SR and aryl-Ni-OAr species to furnish aryl exchanged compounds.
A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent
Anselmi, Silvia,Liu, Siyu,Kim, Seong-Heun,Barry, Sarah M.,Moody, Thomas S.,Castagnolo, Daniele
supporting information, p. 156 - 161 (2021/01/14)
A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed exploiting CALB and using AcOEt with a dual role of more environmentally friendly reaction solvent and enzyme substrate. A series of sulfoxides, including the drug omeprazole, have been synthesised in high yields and with excellent E-factors.
Enantioselective nitrene transfer to sulfides catalyzed by a chiral iron complex
Wang, Jun,Frings, Marcus,Bolm, Carsten
supporting information, p. 8661 - 8665 (2013/09/12)
Iron works: Enantioselective nitrene transfer to sulfide was accomplished by a chiral iron(III)/PyBOX catalyst (see scheme). Various sulfimides were thus obtained in high enantioselectivities and yields. Applications of this protocol to the syntheses of enantioenriched sulfoximines and an epoxide were also demonstrated. Copyright
Discovery of potent, selective, and orally bioavailable alkynylphenoxyacetic acid CRTH2 (DP2) receptor antagonists for the treatment of allergic inflammatory diseases
Crosignani, Stefano,Prêtre, Adeline,Jorand-Lebrun, Catherine,Fraboulet, Ga?le,Seenisamy, Jeyaprakashnarayanan,Augustine, John Kallikat,Missotten, Marc,Humbert, Yves,Cleva, Christophe,Abla, Nada,Daff, Hamina,Schott, Olivier,Schneider, Manfred,Burgat-Charvillon, Fabienne,Rivron, Delphine,Hamernig, Ingrid,Arrighi, Jean-Fran?ois,Gaudet, Marilène,Zimmerli, Simone C.,Juillard, Pierre,Johnson, Zoe
experimental part, p. 7299 - 7317 (2011/12/15)
New phenoxyacetic acid antagonists of CRTH2 are described. Following the discovery of a hit compound by a focused screening, high protein binding was identified as its main weakness. Optimization aimed at reducing serum protein binding led to the identification of several compounds that showed not only excellent affinities for the receptor (41 compounds with Ki 50 100 nM; PGD2-induced eosinophil shape change). Additional optimization of the PK characteristics led to the identification of several compounds suitable for in vivo testing. Of these, 19k and 19s were tested in two different pharmacological models (acute FITC-mediated contact hypersensitivity and ovalbumin-induced eosinophilia models) and found to be active after oral dosing (10 and 30 mg/kg).
PHENOXY ACETIC ACID DERIVATIVES
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Page/Page column 75, (2010/09/03)
The present invention provides phenoxyacetic acid derivatives of Formula (I) for the treatment of CRTH2 related disorders and disease selected from asthma, atopic dermatitis and inflammatory dermatoses.
Selective trifluorination of alkyl aryl sulfides using IF5
Ayuba, Shinichi,Hiramatsu, Chiharu,Fukuhara, Tsuyoshi,Hara, Shoji
, p. 11445 - 11451 (2007/10/03)
In the reaction of IF5 with alkyl aryl sulfides in heptane under reflux conditions, the arylthio group migrated once and three fluorine atoms were selectively introduced on the alkyl chain. In order to find the reason why the reaction stopped at the trifluorination step, we examined the oxidation potentials of the starting material, a reaction intermediate, and the product, and the time course of the reactions. Graphical Abstract.
Reductive α-substitution of sulfoxides with grignard reagents promoted by a magnesium amide
Kobayashi, Kazuhiro,Yokota, Kouichi,Akamatsu, Hideki,Morikawa, Osamu,Konishi, Hisatoshi
, p. 441 - 443 (2007/10/03)
The reactions of sulfoxides bearing α-hydrogen(s) (RSOCHR1R2: R-alkyl or aryl; R1, R2 = H, alkyl, or aryl) with Grignard reagents (R3MgBr: R3 = Et, Ph, or vinyl) in the presence of the diisopropylaminomagnesium reagent, generated in situ by the treatment of diisopropylamine with the appropriate Grignard reagents in diethyl ether, have resulted in the formation of the corresponding sulfides (RSCR1R2R3) in moderate to good isolated yields.
Process for preparing thio, dithio or carbonyl compounds
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, (2008/06/13)
A process is disclosed for the preparation of compounds of the Formula I wherein X is thio, dithio or carbonyl and R and R1 are defined hereinbelow which comprises reducing a compound of the Formula II wherein A is chlorosulfonyl or a group of the Formula STR1 with a sulfur compound comprising sulfur which is of the (+)4 oxidation degree and is converted into the (+)6 oxidation degree during the process or with a sulfur compound which is decomposed in acidic medium to a compound of the latter oxidation degree in the presence of a catalytic amount but not more than 0.5 mole--related to 1 mole of the starting material of the Formula II--of elemental iodine or a compound capable of delivering hydrogen iodide in acidic medium or a compound which can be reduced to hydrogen iodide in acidic medium with the sulfur compound used.
MODERN FRIEDEL-CRAFTS CHEMISTRY. XIV. ON THE CYCLIZATION OF SELECTED ARYL HYDROXYALKYL SULFIDES
El-Khawaga, A. M.,El-Zohry, M. F.,Ismail, M. T.,Abdel-Wahab, A. A.,Khalaf, A. A.
, p. 265 - 270 (2007/10/02)
The feasibility of cycloalkylation reactions in the presence of Friedel-Crafts catalysts was demonstrated in a nimber of aryl hydroxyalkyl sulfides (1-5), and benzyl hydroxyalkyl sulfides (6-7).Treatment of compounds (1-7) with Friedel-Crafts catalysts gave diaryl disulfides, diaryl sulfides, arene thiols, chlorohydrins, aryl chloroalkyl sulfides, aryl alkenyl sulfides and cyclization products.It is noteworthy to mention that cyclization products were isolated only in cases where the hydroxyl group is linked to a tertiary carbon atom as in compounds 3 and 7.A suitable reaction pathway is suggested to rationalize the formation of the various reaction products.
MODERN FRIEDEL-CRAFTS CHEMISTRY. XI. CYCLIZATION OF ARYL HALOALKYL SULFONES, ARYLSULFONYLACYL CHLORIDES AND THEIR CORRESPONDING SULFIDES
Abdel-Wahab, Aboel-Magd A.,El-Khawaga, Ahmed M.,El-Zohry, Maher F.,Khalaf, Ali A.
, p. 31 - 44 (2007/10/02)
The sulfone group deactivation for cyclialkylation and cycliacylation reactions in the presence of Friedel-Crafts catalysts was demonstrated in a number of aryl chloroalkylsulfones (1-8) and arylsulfonylacyl chlorides (17a-22a), respectively.As expected, the corresponding arylchloroalkyl sulfides (9-16) and arylmercaptoacyl chlorides (13a-28a) underwent ring-closure reaction in most cases under the same conditions.The ease of cyclization was governed by the ring size, the stability of the attacking carbocation and the nucleophilicity of the aryl moiety.Also, the behaviour of benzyl sulfones (29, 31a, and 32a) and sulfides (33, 34a and 36a) was inconsistent.Noteworthy, the Friedel-Crafts cyclization reaction is thus considered an accessible method for the synthesis of compounds 37-41 and 45, 51.
