cas 30506-30-0, 1-Bromo-4-(ethylthio)benzene

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Production of Alkyl Aryl Sulfides from Aromatic Disulfides and Alkyl Carboxylates via a Disilathiane–Disulfide Interchange Reaction
The results of this study show that disilathiane is an effective mediator in the synthesis of alkyl aryl sulfides with disulfides and alkyl carboxylates. Mechanistic studies suggest that disilathiane promotes cleavage of the sulfur–sulfur bond of disulfides to generate thiosilane as a key intermediate. Diselenides were also applicable to this transformation to produce the corresponding selenides.
Nakajima, Takumi,Takano, Ken,Maeda, Hiromu,Ogiwara, Yohei,Sakai, Norio
supporting information
p. 4103 - 4107
(2021/11/10)

A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent
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.
Anselmi, Silvia,Liu, Siyu,Kim, Seong-Heun,Barry, Sarah M.,Moody, Thomas S.,Castagnolo, Daniele
supporting information
p. 156 - 161
(2021/01/14)

Copper-Catalyzed Three-Component Coupling Reaction of Aryl Iodides, a Disilathiane, and Alkyl Benzoates Leading to a One-Pot Synthesis of Alkyl Aryl Sulfides
A copper-catalyzed three-component coupling reaction of aryl iodides, hexamethyldisilathiane and alkyl benzoates leading to alkyl aryl sulfides has been demonstrated. A disilathiane acted as both a sulfur source and a promoter of the sulfidation, and the alkyl moiety of the alkyl benzoate was effectively introduced on one side of the sulfide. Moreover, we found that the protocol can be expanded to the preparation of ethyl phenyl selenide with diphenyl diselenide.
Sakai, Norio,Maeda, Hiromu,Ogiwara, Yohei
p. 2323 - 2330
(2019/05/24)

Environmentally benign indole-catalyzed position-selective halogenation of thioarenes and other aromatics
Halogenated aromatic compounds are the cores of many pharmaceutical, agricultural and chemical products but they are commonly prepared using electrophilic halogenation reactions in non-green chlorinated solvents under harsh conditions. A separate problem happens in the aromatic halogenation of thioarenes because they readily undergo oxidative side-reactions. Herein we report an environmentally benign electrophilic bromination of aromatics using an indole-catalytic protocol, which is suitable for a wide range of substrates including thioarenes.
Shi, Yao,Ke, Zhihai,Yeung, Ying-Yeung
supporting information
p. 4448 - 4452
(2018/10/17)

MODULATORS OF ROR-GAMMA
Provided are novel compounds of Formula I: pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful in the treatment of diseases and disorders mediated by RORy. Also provided are pharmaceutical compositions comprising the novel compounds of Formula I and methods for their use in treating one or more inflammatory, metabolic, autoimmune and other diseases or disorders.
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Paragraph 00125; 00126

(2017/06/12)

BENZIMIDAZOLE DERIVATIVES AS MODULATORS OF ROR-GAMMA
Provided are novel compounds of Formula I: pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful in the treatment of diseases and disorders mediated by RORy. Also provided are pharmaceutical compositions comprising the novel compounds of Formula I and methods for their use in treating one or more inflammatory, metabolic, autoimmune and other diseases or disorders.
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Paragraph 00199-00200

(2017/08/21)

DIHYDROPYRROLOPYRIDINE INHIBITORS OF ROR-GAMMA
Provided are novel compounds of Formula (I): pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful in the treatment of diseases and disorders mediated by RORy. Also provided are pharmaceutical compositions co
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Paragraph 00144

(2016/05/24)

DIHYDROPYRROLOPYRIDINE INHIBITORS OF ROR-GAMMA
Provided are novel compounds of Formula (I): pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful in the treatment of diseases and disorders mediated by RORγ. Also provided are pharmaceutical compositions comprising the novel compounds of Formula (I) and methods for their use in treating one or more inflammatory, metabolic, autoimmune and other diseases or disorders.
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Paragraph 0115; 0116

(2016/06/01)

Dihydropyrrolopyridine inhibitors of ROR-gamma
Provided are novel compounds of Formula (I): pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful in the treatment of diseases and disorders mediated by RORγ. Also provided are pharmaceutical compositions co
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Page/Page column 45; 46

(2016/11/21)

OXAZOLIDINONE HYDROXAMIC ACID COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS
This invention pertains generally to treating bacterial infections using organic compounds of Formula I. In certain aspects, the invention pertains to treating infections caused by Gram-negative bacteria. (I) wherein X, Y, R1, R2, R3, R4 and R5 and defined herein.
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Page/Page column 174; 175

(2015/05/19)

An eco-friendly asymmetric organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes: Application on the synthesis of chiral indoles
The asymmetric Michael addition of malonates to α,β-unsaturated aldehydes using a modified Jorgensen-Hayashi organocatalyst in EtOH:brine solvent media is reported. The procedure proceeds smoothly to afford the corresponding Michael adducts in good yields with excellent enantioselectivities. The resulting Michael adducts represent excellent building blocks for the synthesis of chiral indoles. The asymmetric Michael reaction using a modified Jorgensen-Hayashi organocatalyst in EtOH:brine solvent media is reported. This procedure afforded the corresponding Michael adducts in good yields and with excellent enantioselectivities. The resulting adducts were further used as chiral building blocks for the synthesis of indoles. Copyright
Feu, Karla Santos,Deobald, Anna Maria,Narayanaperumal, Senthil,Correa, Arlene G.,Weber Paixao, Marcio
supporting information
p. 5917 - 5922
(2013/09/23)

Identification of biaryl sulfone derivatives as antagonists of the histamine H3 receptor: Discovery of (R)-1-(2-(4′-(3- methoxypropylsulfonyl)biphenyl-4-yl)ethyl)-2-methylpyrrolidine (APD916)
The design of a new clinical candidate histamine-H3 receptor antagonist for the potential treatment of excessive daytime sleepiness (EDS) is described. Phenethyl-R-2-methylpyrrolidine containing biphenylsulfonamide compounds were modified by re
Semple, Graeme,Santora, Vincent J.,Smith, Jeffrey M.,Covel, Jonathan A.,Hayashi, Rena,Gallardo, Charlemagne,Ibarra, Jason B.,Schultz, Jeffrey A.,Park, Douglas M.,Estrada, Scott A.,Hofilena, Brian J.,Smith, Brian M.,Ren, Albert,Suarez, Marissa,Frazer, John,Edwards, Jeffrey E.,Hart, Ryan,Hauser, Erin K.,Lorea, Jodie,Grottick, Andrew J.
supporting information; experimental part
p. 71 - 75
(2012/02/16)

High birefringence nematic liquid crystals for display and telecom applications
Several compounds with high birefringence and, having tolane structure were synthesized. For a high polarizability, isothiocyanato (NCS) terminal group was introduced. Another goal of this study was reduction of melting point and smectic phases by introduction of fluorine as lateral substituent. The transition temperatures for all the synthesized compounds and the refractive and dielectric indices for one of the compounds have been determined. Electro-optic (EO) measurements were also performed.
Catanescu, Carmen Otilia,Chien,Wu, Shin-Tson
p. 93/[1135]-102/[1144]
(2007/10/03)

A mild protocol for the deoxygenation of α-hydrogen-containing sulfoxides to the corresponding sulfides
A mild method for the deoxygenation of α-hydrogen-containing sulfoxides to sulfides is reported. This synthetically useful and operationally simple protocol derives mechanistically from the Swern oxidation methodology.
Bhatia, Gurpreet S.,Graczyk, Piotr P.
p. 5193 - 5195
(2007/10/03)

Oxidation of organic sulfides by Br2 and H2O2. Electrophilic and free-radical processes
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Bravo,Dordi,Fontana,Minisci
p. 3232 - 3234
(2007/10/03)

Synthesis of functional aromatic multisulfonyl chlorides and their masked precursors
The synthesis of functional aromatic bis(sulfonyl chlorides) containing an acetophenone and two sulfonyl chloride groups, i.e., 3,5-bis[4-(chlorosulfonyl)phenyl]-1-acetophenone (16), 3,5-bis(chlorosulfonyl)-1-acetophenone (17), and 3,5-bis(4-(chlorosulfonyl)phenyloxy)-1-acetophenone (18) via a sequence of reactions, involving in the last step the quantitative oxidative chlorination of S-(aryl)-N,N′-diethylthiocarbamate, alkyl- or benzyl thiophenyl groups as masked nonreactive precursors to sulfonyl chlorides is described. A related sequence of reactions was used for the synthesis of the aromatic trisulfonyl chloride 1,1,1-tris(4-chlorosulfonylphenyl)ethane (24). 4-(Chlorosulfonyl)phenoxyacetic acid, 2,2-bis[[[4-(chlorosulfonyl)phenoxyacetyl]oxy]methyl]-1,3-propanediyl ester (27), 5,11,17,23-tetrakis(chlorosulfonyl)-25,26,27,28-tetrakis (ethoxycarbonylmethoxy)calix[4]arene (38), 5,11,17,23,29,35-hexakis(chlorosulfonyl)-37,38,39,40,41,42-hexakis (ethoxycarbonylmethoxy)calix[6]arene (39), 5,11,17,23,29,35,41,47-octakis (chlorosulfonyl)-49,50,51,52,53,54,55,56-octakis(ethoxycarbonylmethoxy) calix[8]arene (40), 5,11,17,23-tetrakis(tert-butyl)-25,26,27,28-tetrakis(chlorosulfonyl phenoxyacetoxy)calix[4]arene (44), 5,11,17,23,29,35-hexakis(tert-butyl)-37,38,39,40,41,42-hexakis (chlorosulfonylphenoxyacetoxy)calix[6]arene (45), and 5,11,17,23,29,35,41,47-octakis (tert-butyl)-49,40,51,52,53,54,55,56-octakis (chlorosulfonylphenoxyacetoxy)calix[8]arene (46) were synthesized by two different multistep reaction procedures, the last step of both methods consisting of the chlorosulfonation of compounds containing suitable activated aromatic positions. 2,4,6-Tris(chlorosulfonyl)aniline (47) was obtained by the chlorosulfonation of aniline. The conformation of two series of multisulfonyl chlorides i.e., 38, 39, 40 and 44, 45, 46, was investigated by 1H NMR spectroscopy. The masked nonreactive precursor states of the functional aromatic multisulfonyl chlorides and the aromatic multisulfonyl chlorides reported here represent the main starting building blocks required in a new synthetic strategy elaborated for the preparation of dendritic and other complex organic molecules.
Percec,Bera,De Binod,Sanai,Smith,Holerca,Barboiu,Grubbs,Frechet
p. 2104 - 2117
(2007/10/03)

Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 15. Generation of alkoxycarbonyl(sulfenyl)carbenes and their intramolecular insertion to give alkenyl sulfides
A range of 18 alkoxycarbonyl sulfinyl phosphorus ylides 9 have been prepared and their behaviour upon flash vacuum pyrolysis (FVP) at 600 deg C examined. For R1 = H, Me and Et they lose Ph3PO and in some cases Ph3P to give mixtures of products including the alkenyl sulfides 10, the sulfides 11, the disulfides 12 and the thioesters 14. The alkenyl sulfides 10 most likely arise from intramolecular insertion of the alkoxycarbonyl sulfenyl carbenes resulting from loss off Ph3PO to produce β-lactones which then lose CO2 and this is supported by the results from 13C labelled ylides. Possible mechanisms for the formation of 11 and 14 are also presented and the feasibility of various steps has been examined by preparation and pyrolysis of the proposed intermediates. In contrast, pyrolysis of the ylides 9 where R1 = Ph and the tert-butoxycarbonyl ylides 30 leads mainly to complete fragmentation with loss of Ph3PO and benzyl alcohol or 2-methylpropan-2-ol and does not give any useful sulfur-containing products. Four alkoxy-carbonyl sulfonyl diazo compounds 33 have been prepared and in three cases they give the alkenyl sulfones 34 upon FVP at 400 deg C, probably by an intramolecular insertion and decarboxylation process analogous to the formation of 10 from 9. On the other hand the alkoxycarbonyl carbenes produced by FVP of the amino acid-derived diazo compounds 35 undergo alternative proocesses with no sign of β-lactone formation. Fully assigned 13C NMR data are presented for 13 of the ylides.
Aitken, R. Alan,Armstrong, Jill M.,Drysdale, Martin J.,Ross, Fiona C.,Ryan, Bruce M.
p. 593 - 604
(2007/10/03)

Flash Vacuum Pyrolysis of Alkoxycarbonyl/Sulfinyl Stabilised Phosphorus Ylides: Generation and Intramolecular Insertion of Alkoxycarbonyl(sulfenyl)carbenes
Flash vacuum pyrolysis of phosphorus ylides stabilised both by ester and sulfinyl groups results mainly in extrusion of Ph3PO to generate alkoxycarbonyl(sulfenyl)carbenes; these undergo intramolecular insertion into CH of the alkoxycarbonyl group giving β-lactones which under the conditions lose CO2 to afford alkenyl sulfides.
Aitken, R. Alan,Drysdale, Martin J.,Ryan, Bruce M.
p. 805 - 806
(2007/10/02)

PREPARATION OF PHENYL ARYL SULFIDES BY REACTION OF BENZYNE WITH ETHYL ARYL SULFIDES
A variety of ethyl aryl sulfides (1) react with benzyne, with evolution of ethylene, to give phenyl aryl sulfides (3) in excellent yields, thus providing a general synthesis of 3 from arenethiols since 1 are quantitatively obtainable from arenethiols and ethyl bromide.
Nakayama, Juzo,Fujita, Toko,Hoshino, Masamatsu
p. 249 - 250
(2007/10/02)