- B2cat2-Mediated Reduction of Sulfoxides to Sulfides
-
An efficient and operationally simple method for the reduction of sulfoxides to sulfides has been developed using bis(catecholato)diboron (B2cat2) as a reducing agent. The present method accommodates various functional groups which are generally prone to reduction: halides, alkynes, carbonyls, nitriles, and heterocycles are totally intact, and only sulfoxide moieties undergo reduction chemoselectively. Moreover, the remaining diboron and the resulting boron-containing wastes are readily removable, the practicality of this protocol being thus demonstrated.
- Takahashi, Fumiya,Nogi, Keisuke,Yorimitsu, Hideki
-
supporting information
p. 3009 - 3012
(2020/03/25)
-
- Increasing Complexity: A Practical Synthetic Approach to Three-Dimensional, Cyclic Sulfoximines and First Insights into Their in Vitro Properties
-
A short synthetic approach with broad scope to access five- to seven-membered cyclic sulfoximines in only two to three steps from readily available thiophenols is reported. Thus, simple building blocks were converted to complex molecular structures by a s
- Boulard, Emilie,Ganzer, Ursula,Lücking, Ulrich,Lienau, Philip,Oertel, Luisa,Sch?fer, Martina,Zibulski, Vivien
-
-
- Synthesis of α-Cyano and α-Sulfonyl Cyclic Ethers via Intramolecular Reactions of Peroxides with Sulfone- And Nitrile-Stabilized Carbanions
-
The intramolecular reaction of carbon nucleophiles with oxygen-centered electrophiles has been little explored outside of nucleophilic epoxidation. We now report the synthesis of sulfonyl- and cyano-substituted oxacycles via intramolecular reaction of sul
- Horn, Alissa,Dussault, Patrick H.
-
p. 14611 - 14626
(2019/11/13)
-
- Synergetic Effect of Monomer Functional Group Coordination in Catalytic Insertion Polymerization
-
PhS- and PhNH-functionalized dienes are copolymerized efficiently with butadiene to stereoregular copolymers by [(mesitylene)Ni(allyl)][BArF4] (Ni-1). Overall polymerization rates and comonomer incorporations depend strongly on the l
- Leicht, Hannes,G?ttker-Schnetmann, Inigo,Mecking, Stefan
-
supporting information
p. 6823 - 6826
(2017/05/31)
-
- NR2B SELECTIVE NMDA-RECEPTOR ANTAGONISTS FOR TREATMENT OF IMMUNE-MEDIATED INFLAMMATORY DISEASES
-
The present invention provides novel means and methods for treatment auf immunemediated inflammatory diseases.
- -
-
Paragraph 161
(2017/03/21)
-
- Palladium-catalyzed Mizoroki-Heck-type reactions of [Ph2SRfn][OTf] with alkenes at room temperature
-
The first Pd-catalyzed Mizoroki-Heck-type reaction of [Ph2SRfn][OTf] with alkenes is described. The reaction of [Ph2SRfn][OTf] (Rfn = CF3, CH2CF3) with alkenes in the presence of 10 mol% Pd[P(t-Bu)3]2 and TsOH at room temperature provided the corresponding phenylation products in good to high yields. The bases that benefit the traditional Mizoroki-Heck reactions severely inhibited the transformation with [Ph2SRfn][OTf], whereas acids significantly improved the reaction. This protocol supplies a new class of cross-coupling partners for Mizoroki-Heck-type reactions and gains important insights into the reactivity of phenylsulfonium salts either with or without fluorine-containing alkyl groups as the promising phenylation reagents in organic synthesis.
- Wang, Shi-Meng,Song, Hai-Xia,Wang, Xiao-Yan,Liu, Nan,Qin, Hua-Li,Zhang, Cheng-Pan
-
supporting information
p. 11893 - 11896
(2016/10/09)
-
- Pd-catalyzed Suzuki–Miyaura cross-coupling of [Ph2SR][OTf] with arylboronic acids
-
The Pd-catalyzed Suzuki–Miyaura cross-coupling of alkyl- and fluoroalkyl(diphenyl)sulfonium triflates with arylboronic acids was compared. The fluorine substitution on the alkyl groups of [Ph2SR][OTf] had a big influence on the reaction. Perfluoroalkyl(diphenyl)sulfonium triflates (2b–d) were unsuccessful participants in the Pd-catalyzed phenylation of arylboronic acid under the standard conditions because of the strong electronegativity of the long-chain perfluoroalkyl groups, which underwent S[sbnd]Rfnbond cleavage instead. Polyfluoroalkyl(diphenyl)sulfonium triflates (2f–h) reacted with arylboronic acid to afford the phenylation product in very low yields due to the tendency of deprotonation and β-F elimination of the sulfonium salts. Eventually, (2,2,2-trifluoroethyl)diphenylsulfonium triflate (2e), methyl- or ethyl(diphenyl)sulfonium triflate (2i or 2j), and triphenylsulfonium triflate (2m) were found to be more effective reagents than other tested phenylsulfounium salts for Pd-catalyzed phenylation, which provided much higher yields of the desired products under mild conditions.
- Wang, Xiao-Yan,Song, Hai-Xia,Wang, Shi-Meng,Yang, Jing,Qin, Hua-Li,Jiang, Xin,Zhang, Cheng-Pan
-
p. 7606 - 7612
(2016/11/11)
-
- Base-free palladium-catalyzed cross-coupling of arylsulfonium salts with sodium tetraarylborates
-
Palladium-catalyzed cross-coupling reactions of arylsulfonium salts with sodium tetraarylborates were found to proceed smoothly without recourse to an additional base, providing a new, reliable route to biaryls from organosulfur compounds.
- Osuka, Atsuhiro,Vasu, Dhananjayan,Yorimitsu, Hideki
-
p. 3286 - 3291
(2020/10/20)
-
- SUBSTITUTED BENZOXAZOLONE DERIVATIVES AS ACID CERAMIDASE INHIBITORS, AND THEIR USE AS MEDICAMENTS
-
The present invention relates to substituted benzoxazolone derivatives as acid ceramidase inhibitors, pharmaceutical compositions containing these inhibitors and methods of inhibiting acid ceramidase for the treatment of disorders in which modulation of the levels of ceramide is clinically relevant. The invention also provides substituted benzoxazolone derivatives for use in the treatment of cancer, inflammation, pain, inflammatory pain or pulmonary diseases.
- -
-
Page/Page column 21; 39; 40; 48
(2015/12/31)
-
- NR2B-SELECTIVE NMDA-RECEPTOR ANTAGONISTS
-
The present invention relates to compounds according to general formula (I) and pharmaceutical compositions comprising compounds according to general formula (I).
- -
-
Page/Page column 47
(2010/11/05)
-
- Three component reaction of arynes with cyclic ethers and active methines: Synthesis of ω-trichloroalkyl phenyl ethers
-
Synthesis of ω-chlorinated alkyl phenyl ethers by tandem reaction of arynes with cyclic ethers and active methines was achieved. Reaction of benzenediazonium 2-carboxylate with tetrahydropyran or tetrahydrofuran in refluxing chloroform afforded 6,6,6-trichlorohexyl phenyl ether or 5,5,5-trichloropentyl phenyl ether in 40% and 61% yields, respectively. When dichloroacetonitrile was used as a reactant, 5,5-dichloro-5-cyanopentyl phenyl ether was obtained in 61% yield. While benzenediazonium carboxylate did not react with epoxides, reaction of benzyne derived from 2-(trimethylsilyl)phenyl triflate with epoxides afforded 3,3,3-trichloropropyl phenyl ethers in good yields as isomeric mixtures. The reaction of oxetanes with benzyne was also reported.
- Okuma, Kentaro,Fukuzaki, Yuta,Nojima, Akiko,Sou, Ayumi,Hino, Haruna,Matsunaga, Nahoko,Nagahora, Noriyoshi,Shioji, Kosei,Yokomori, Yoshinobu
-
experimental part
p. 1238 - 1247
(2010/12/20)
-
- Synthesis and pharmacological evaluation of benzamide derivatives as selective 5-HT4 receptor agonists
-
It is thought that selective 5-HT4 receptor agonists-such as 4-amino-5-chloro-2-methoxy-N-[1-(6-oxo-6-phenylhexyl)piperidin-4-ylmethyl] benzamide (2)-have the ability to enhance both upper and lower gastrointestinal motility without any significant adverse effects. Modification of 2 was performed. Variation of the piperidin-4-ylmethyl moiety of 2 led to a decrease in the binding affinity for the 5-HT4 receptor. Following conversion of the carbonyl group on the benzoyl part to a hydroxyl or sulfoxide group, the binding affinity for the 5-HT4 receptor was retained although the effect on defecation was reduced. Many of the 4-amino-5-chloro-2-methoxy-N- (piperidin-4-ylmethyl)benzamides that had a ether or sulfide moiety in the side-chain part at the 1-position of the piperidine exhibited high affinity for the 5-HT4 receptor. Among these, phenylthio 41c and benzylthio derivative 44 were selective 5-HT4 receptor agonists, and had a similar effect on defecation to compound 2.
- Sonda, Shuji,Kawahara, Toshio,Katayama, Kenichi,Sato, Noriko,Asano, Kiyoshi
-
p. 3295 - 3308
(2007/10/03)
-
- Synthesis and pharmacological properties of benzamide derivatives as selective serotonin 4 receptor agonists
-
A series of 4-amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamides with a polar substituent group at the 1-position of the piperidine ring was synthesized and evaluated for its effect on gastrointestinal motility. The benzoyl, phenylsulfonyl, and benzylsulfonyl derivatives accelerated gastric emptying and increased the frequency of defecation. One of them, 4-amino-N-[1-[3-(benzylsulfonyl)propyl]piperidin-4-ylmethyl]-5-chloro-2- methoxybenzamide (13a, Y-36912), was a selective 5-HT4 receptor agonist offering potential as a novel prokinetic with reduced side effects derived from 5-HT3- and dopamine D2 receptor-binding affinity. In the oral route of administration, this compound enhanced gastric emptying and defecation in mice, and has a possibility as a prokinetic agent, which is effective on both the upper and the lower gastrointestinal tract.
- Sonda, Shuji,Katayama, Kenichi,Kawahara, Toshio,Sato, Noriko,Asano, Kiyoshi
-
p. 2737 - 2747
(2007/10/03)
-
- Design and synthesis of orally active benzamide derivatives as potent serotonin 4 receptor agonist
-
A series of 4-amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide derivatives bearing an aralkylamino, alkylamino, benzoyl or phenylsulfonyl group at its side chain part at the 1-position on the piperidine ring was synthesized. They were evaluated
- Sonda, Shuji,Kawahara, Toshio,Murozono, Takahiro,Sato, Noriko,Asano, Kiyoshi,Haga, Keiichiro
-
p. 4225 - 4234
(2007/10/03)
-
- Hexitol derivatives having vasodilative activity
-
Disclosed is a hexitol derivative represented by the formula (I): STR1 wherein Q represents a formula selected from the group consisting of STR2 wherein a represents NH, O or S; each of b, c and d independently represents CH or N; each of R1, R2, R3 and R4 independently represents hydrogen, lower alkyl, trifluoromethyl, aryl, lower alkanoyloxy, amino, lower alkylamino, lower alkanoylamino, lower alkanoyl, aroyl, halogen, nitro, (CH2)m OR 7, (CH2)m SR7, (CH2)m CO2 R7 where R7 represents hydrogen or lower alkyl and m represents an integer of 0 to 3; each of R5 and R6 independently represents hydrogen or lower alkyl; U represents >N-- or STR3 W represents a single bond, --O-- or --S--; X represents STR4 wherein each of Y1 and Y2 independently represents hydrogen, lower alkyl, hydroxyl, lower alkanoyloxy, nitrile or phenyl; or Y1 and Y2 are combined together to form oxygen; each of Y3 and Y4 independently represents hydrogen or lower alkyl; and l is an integer of 0 to 6, and where l is an integer of 2 to 6, each STR5 may be the same or different; Z represents hydrogen or nitro; and, n is 2 or 3 or a pharmaceutically acceptable salt thereof. The compounds show prominent coronary vasodilative activities, and are useful in treating angina pectoris and myocardial infarction.
- -
-
-
- THE COMPATIBILITY OF THE CYANO AND ALKYL CHLORIDE FUNCTIONS IN PHENYLTHIOALKYLATION REACTIONS OF O-SILYLATED ENOLATES
-
The compatibility of the cyano group and of chlorides with the conditions of phenylthioalkylation of O-silylated enolates has been demonstrated.
- Lee, Thomas V.,Visani, Naina
-
p. 5559 - 5560
(2007/10/02)
-