- Single-Step Sulfur Insertions into Iron Carbide Carbonyl Clusters: Unlocking the Synthetic Door to FeMoco Analogues
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The one-step syntheses, X-ray structures, and spectroscopic characterization of synthetic iron clusters, bearing either inorganic sulfides or thiolate with interstitial carbide motifs, are reported. Treatment of iron carbide carbonyl clusters [Fen/s
- Joseph, Chris,Cobb, Caitlyn R.,Rose, Michael J.
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- Intramolecular Chalcogenylation of Isooxazolines Mediated by PhICl 2and Diorganyl Disulfides or Diselenides
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Reactive organosulfenyl chlorides (ArSCl) or selenenyl chlorides (ArSeCl), generated in situ from the reaction of PhICl 2with diorganyl disulfides or diselenides, enable the intramolecular oxidative cyclization/chalcogenylation of β,γ-unsaturated oximes, leading to the formation of a series of chalcogenylated isooxazolines in good to excellent yield.
- Zhang, Dongke,Zhang, Jingran,Li, Xiaoxian,Yu, Zhenyang,Li, Yadong,Sun, Fengxia,Du, Yunfei
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p. 411 - 420
(2021/10/05)
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- Synthesis of 4-chalcogenyl pyrazoles via electrophilic chalcogenation/cyclization of α,β-alkynic hydrazones
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A facile method for the synthesis of 4-chalcogenylated pyrazoles has been developed via electrophilic chalcogenation/cyclization of α,β-alkynic hydrazones. The cyclization of α,β-alkynic aldehyde hydrazones could be induced by using either sulfenyl chloride or the S-electrophiles generated in situ from the reaction of NCS and arythiol. The developed method was successfully applied to the synthesis of the sulfenyl analogue of celecoxib.
- Cheng, Yu-Fei,Gao, Wen-Chao,Niu, Yulan,Shang, Yu-Zhu,Tian, Jun,Yu, Xinzhang
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p. 1806 - 1811
(2020/03/17)
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- Development of disulfide-derived fructose-1,6-bisphosphatase (FBPase) covalent inhibitors for the treatment of type 2 diabetes
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Fructose-1,6-bisphosphatase (FBPase), as a key rate-limiting enzyme in the gluconeogenesis (GNG) pathway, represents a practical therapeutic strategy for type 2 diabetes (T2D). Our previous work first identified cysteine residue 128 (C128) was an important allosteric site in the structure of FBPase, while pharmacologically targeting C128 attenuated the catalytic ability of FBPase. Herein, ten approved cysteine covalent drugs were selected for exploring FBPase inhibitory activities, and the alcohol deterrent disulfiram displayed superior inhibitory efficacy among those drugs. Based on the structure of lead compound disulfiram, 58 disulfide-derived compounds were designed and synthesized for investigating FBPase inhibitory activities. Optimal compound 3a exhibited significant FBPase inhibition and glucose-lowering efficacy in vitro and in vivo. Furthermore, 3a covalently modified the C128 site, and then regulated the N125–S124–S123 allosteric pathway of FBPase in mechanism. In summary, 3a has the potential to be a novel FBPase inhibitor for T2D therapy.
- Xu, Yi-xiang,Huang, Yun-yuan,Song, Rong-rong,Ren, Yan-liang,Chen, Xin,Zhang, Chao,Mao, Fei,Li, Xiao-kang,Zhu, Jin,Ni, Shuai-shuai,Wan, Jian,Li, Jian
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- Trichloroisocyanuric acid-promoted thiolation of phosphites by thiols
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A simple and convenient method for the synthesis of thiophosphates by coupling of phosphites with thiols under mild conditions has been developed. The reactions were promoted by trichloroisocyanuric acid (TCCA) and were carried out at room temperature in
- Chen, Yingying,Li, Meichao,Gong, Zhangshui,Shen, Zhenlu
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- Synergistic Dual Role of [hmim]Br-ArSO2Cl in Cascade Sulfenylation-Halogenation of Indole: Mechanistic Insight into Regioselective C-S and C-S/C-X (X = Cl and Br) Bond Formation in One Pot
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Bifunctionalized indoles are an important class of biologically active heterocyclic compounds and potential drug candidates. Because of the lack of efficient synthetic methods, one pot cascade synthesis of these compounds is rare and remains a challenge.
- Equbal, Danish,Singh, Richa,Saima,Lavekar, Aditya G.,Sinha, Arun K.
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supporting information
p. 2660 - 2675
(2019/03/14)
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- Synthetic method of aryl sulfur chlorine or aryl selenium chlorine
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The invention discloses a synthetic method of aryl sulfur chlorine or aryl selenium chlorine. The synthetic method comprises the following steps that diaryl disulfide or diaryl diselenide II is dissolved in a solvent and reacts under the action of dichloro-iodobenzene III to obtain aryl sulfur chlorine or aryl selenium chlorine I. In the formula shown in the description, R refers to hydrogen, methyl or halogen, and Y refers to sulfur or selenium. The method has the advantages that the operation is simple, the raw materials are cheap and easy to obtain, the yield is relatively ideal and the cost is low.
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Paragraph 0025-0028
(2019/06/27)
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- In Situ Formation of RSCl/ArSeCl and Their Application to the Synthesis of 4-Chalcogenylisocumarins/Pyrones from o-(1-Alkynyl)benzoates and (Z)-2-Alken-4-ynoates
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The reaction of diorganyl disulfides or diselenides with PhICl2 in acetonitrile was found for the first time to lead to the in situ formation of organosulfenyl chloride or selenenyl chloride, which enables the regioselective intramolecular chalcogenylacyloxylation of alkynes resulting in the formation of 4-chalcogenylisocumarins/pyrones in good to excellent yields under metal-free conditions.
- Xing, Linlin,Zhang, Yong,Li, Bing,Du, Yunfei
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supporting information
p. 3620 - 3624
(2019/05/24)
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- In Situ Activation of Disulfides for Multicomponent Reactions with Isocyanides and a Broad Range of Nucleophiles
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Activation of disulfides with N-halogen succinimide in the presence of TEMPO allows insertion reaction by an isocyanide, the product of which can further accept a wide range of nucleophiles for the generation of isothioureas and related molecular moieties. This new procedure overcomes previous methods that accept essentially only aryl amines as the third nucleophilic component. The diverse nucleophiles usable in our new protocol make this approach a general method for de novo synthesis of many S-containing heterocycles.
- Lei, Xiaofang,Wang, Yuanyuan,Fan, Erkang,Sun, Zhihua
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supporting information
p. 1484 - 1487
(2019/02/26)
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- Unsymmetrical difunctionalization of cyclooctadiene under continuous flow conditions: Expanding the scope of ring opening metathesis polymerization
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Functionalized cyclooctenes (FCOEs) are important monomers in ring-opening metathesis polymerization (ROMP). Herein, a new library of disubstituted FCOEs bearing adjacent heteroatoms were synthesized and applied in ROMP. To address the issues associated w
- Shen, Xianwang,Gong, Honghong,Zhou, Yang,Zhao, Yucheng,Lin, Jun,Chen, Mao
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p. 1846 - 1853
(2018/02/23)
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- Sulfides and Disulfides of s-Triazine: Potential Thermal Thiyl Radical Generators
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A series of aliphatic and aromatic thioethers and dithioethers of s-triazine were synthesised to study their thermal properties, in particular the thermally induced thiyl radical generation ability. Four symmetric s-triazine sulfides of the type (RS)3C3N3, namely 2,4,6-tris(phenylthio)- (1), 2,4,6-tris(para-tolylthio)- (3), 2,4,6-tris(ethylthio)- (5) and 2,4,6-tris(tert-butylthio)-1,3,5-triazine (7), as well as four symmetric s-triazine disulfides of the type (RSS)3C3N3, namely 2,4,6-tris(phenyldithio)- (2), 2,4,6-tris(para-tolyldithio)- (4), 2,4,6-tris(ethyldithio)- (6) and 2,4,6-tris(tert-butyldithio)-1,3,5-triazine (8) were synthesised. All compounds were comprehensively characterised by 1H and 13C NMR, infrared and Raman spectroscopy as well as elemental analyses. Single-crystal X-ray diffraction analyses of 1, 2 and 5 are discussed. The thermal behaviour was studied by thermogravimetric analyses coupled with mass spectrometry (TGA-MS) and quantum chemical calculations. Limiting oxygen index (LOI) flammability tests showed that the disulfides are the most promising radical generators, and are most likely suitable flame retardants for selected polymers.
- H?hne, Carl-Christoph,Posern, Christian,B?hme, Uwe,Kroke, Edwin
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p. 13596 - 13606
(2018/09/19)
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- Generation of 1,2-oxathiolium ions from (arysulfonyl)- and (arylsulfinyl)allenes in Br?nsted acids. NMR and DFT study of these cations and their reactions
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In strong Br?nsted acids (CF3SO3H, FSO3H, D2SO4), (arysulfonyl)allenes (ArSO2-CR1=C=CR2R3) and (arylsulfinyl)allenes (ArSO-CR1=C=CR2R3) undergo cyclization into the corresponding stable 1,2-oxathiolium ions, which were studied by means of NMR and DFT calculations. Quenching of solutions of these cations with low nucleophilic media, aqueous HCl, leads to their deprotonation with a stereoselective formation of (arysulfonyl)butadienes (for instance, ArSO2-CR1=C-C(Me)=CH2, for R2 = R3 = Me, yields of 87-98%). Reactions of (arysulfonyl)allenes in the system TfOH (0.1 equiv)-HFIP (hexafluoropropan-2-ol) followed by hydrolysis give rise to allyl alcohols (ArSO2-CR1=CH-C(OH)R2R3, yields of 78-99%). Reflux of solutions of (arysulfonyl)allenes in the presence of TfOH (1 equiv) in 1,2-dichlorobenzene leads to the cyclization into thiochromene 1,1-diox-ides in high yields. Under the action of TfOH or AlX3 (X = Cl, Br) followed by hydrolysis of reaction mixtures, (arylsulfinyl)allenes give allyl alcohols (ArSO2-CR1=CH-C(OH)R2R3). Plausible reaction mechanisms have been proposed for all studied reactions.
- Lozovskiy, Stanislav V.,Ivanov, Alexander Yu.,Khoroshilova, Olesya V.,Vasilyev, Aleksander V.
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p. 2897 - 2906
(2018/12/13)
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- Generation of Oxazolidine-2,4-diones Bearing Sulfur-Substituted Quaternary Carbon Atoms by Oxothiolation/Cyclization of Ynamides
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A novel method for metal-free oxothiolation of ynamides to construct oxazolidine-2,4-diones bearing sulfur-substituted quaternary carbon atoms has been developed. It represents a rare C-O bond cleavage of ynamides, as well as a facile and tandem approach for the formation of C-O, C-S, and C-Cl bonds. This redox-neutral protocol can be applied to the synthesis of multisubstituted oxazolidine-2,4-diones with good chemoselectivity and good yields of isolated products under mild conditions.
- Huang, Hai,Fan, Junzhen,He, Guangke,Yang, Zhimin,Jin, Xiaodong,Liu, Qi,Zhu, Hongjun
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supporting information
p. 2532 - 2538
(2016/02/12)
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- Formation of α-chalcogenyl acrylamides through unprecedented chalcogen-mediated metal-free oxyfunctionalization of ynamides with DMSO as an oxidant
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A novel chalcogen-mediated oxyfunctionalization mode of ynamides for the synthesis of α-chalcogenyl acrylamides has been developed. Independent of metal catalysts, external oxidants and additives, this mild process afforded a range of structurally diverse
- Huang, Hai,Tang, Luning,Liu, Qi,Xi, Yang,He, Guangke,Zhu, Hongjun
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supporting information
p. 5605 - 5608
(2016/05/09)
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- Synthesis of disaccharide nucleosides by the O-glycosylation of natural nucleosides with thioglycoside donors
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Disaccharide nucleosides constitute an important group of naturally-occurring sugar derivatives. In this study, we report on the synthesis of disaccharide nucleosides by the direct O-glycosylation of nucleoside acceptors, such as adenosine, guanosine, thy
- Aoki, Shin,Fukumoto, Taketo,Itoh, Taiki,Kurihara, Masayuki,Saito, Shigeto,Komabiki, Shin-Ya
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p. 740 - 751
(2015/06/02)
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- Rhodium(I)-catalyzed cycloisomerization of allene-allenylcyclopropanes
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The RhI-catalyzed intramolecular [5+2-2]-type cycloisomerization of allene-allenylcyclopropanes was developed. In this reaction, ethylene was liberated from the cyclopropane ring to afford the 1,5,6,7-tetrahydroazulene skeletons.
- Kawamura, Takamasa,Kawaguchi, Yasuaki,Sugikubo, Katsuya,Inagaki, Fuyuhiko,Mukai, Chisato
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supporting information
p. 719 - 722
(2015/01/30)
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- A metal free chlorothiolation strategy for synthesis of vinyl sulfides from internal alkynoates
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A metal free chlorothiolation approach has been developed for conversion of internal alkynoates to vinyl sulfides and also utilized mild PIDA mediated oxidation to yield the corresponding sulfoxides.
- Surineni, Naresh,Buragohain, Pori,Saikia, Bishwajit,Barua, Nabin C.,Baruah, Rajani K.
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supporting information
p. 6965 - 6969
(2015/11/27)
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- Palladium-catalyzed regio- and stereoselective chlorothiolation of terminal alkynes with sulfenyl chlorides
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Chlorothiolation of terminal alkynes with sulfenyl chlorides yields anti-adducts without transition-metal catalysts. In sharp contrast, transition-metal-catalyzed chlorothiolation has not been developed to date, possibly because organosulfur compounds can poison catalyst. Herein, the regio- and stereoselective palladium-catalyzed chlorothiolation of terminal alkynes with sulfenyl chlorides is described. syn-Chlorothiolation offers a complementary synthetic route to chloroalkenyl sulfides. 2-Chloroalkenyl sulfides can easily be transformed into various sulfur-containing products, most of which are often found in natural products and pharmaceuticals. Copyright
- Iwasaki, Masayuki,Fujii, Tomoya,Yamamoto, Arisa,Nakajima, Kiyohiko,Nishihara, Yasushi
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supporting information
p. 58 - 62
(2014/01/06)
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- Iron-Induced regio- and stereoselective addition of sulfenyl chlorides to alkynes by a radical pathway
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The radical addition of the ClS s-bond in sulfenyl chlorides to various C~C triple bonds has been achieved with excellent regio- and stereoselectivity in the presence of a catalytic amount of a common iron salt. The reaction is compatible with a variety of functional groups and can be scaled up to the gram-scale with no loss in yield. As well as terminal alkynes, internal alkynes underwent stereodefined chlorothiolation to provide tetrasubstituted alkynes. Preliminary mechanistic investigations revealed a plausible radical process involving a sulfur-centered radical intermediate via iron-mediated homolysis of the ClS bond. The resulting chlorothiolation adducts can be readily transformed to the structurally complex alkenyl sulfides by cross-coupling reactions. The present reaction can also be applied to the complementary synthesis of the potentially useful bis-sulfoxide ligands for transition-metal-catalyzed reactions.
- Iwasaki, Masayuki,Fujii, Tomoya,Nakajima, Kiyohiko,Nishihara, Yasushi
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supporting information
p. 13880 - 13884
(2015/01/16)
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- Synthesis and evaluation of novel sulfenamides as novel anti Methicillin-resistant Staphylococcus aureus agents
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A total of 29 novel sulfenamide compounds were synthesized, spectroscopically characterized and evaluated in vitro for antimicrobial activity against various infectious pathogens. Compounds 1b and 2c exhibited potent inhibition against clinical Methicillin-resistant Staphylococcus aureus (MRSA) strains with minimum inhibitory concentration (MIC) values of 1.56 μg/mL.
- Shang, Jian-Li,Guo, Hui,Li, Zai-Shun,Ren, Biao,Li, Zheng-Ming,Dai, Huan-Qin,Zhang, Li-Xin,Wang, Jian-Guo
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supporting information
p. 724 - 727
(2013/02/25)
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- Synthesis and biological evaluation of nonsymmetrical aromatic disulfides as novel inhibitors of acetohydroxyacid synthase
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46 Novel nonsymmetrical aromatic disulfides containing [1,3,4]thiadiazole or [1,3,4]oxadiazole groups were synthesized and their biological activities were evaluated as inhibitors of acetohydroxyacid synthase (AHAS, EC 2.2.1.6). Besides their strong in vitro inhibition against plant AHAS, compounds 3e and 3f also display 80-100% post-emergence herbicidal activities in greenhouse bioassay at 1500 g/ha dosage. The assay of exogenous branched-chain amino acids supplementation on rape root growth of 3e suggests that the herbicidal activity has relationship with AHAS inhibition.
- Li, Zai-Shun,Wang, Wei-Min,Lu, Wei,Niu, Cong-Wei,Li, Yong-Hong,Li, Zheng-Ming,Wang, Jian-Guo
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supporting information
p. 3723 - 3727
(2013/07/25)
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- Sulfur-bridged BODIPY DYEmers
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Reactions of BODIPY monomers with sulfur nucleophiles and electrophiles result in the formation of new BODIPY dimers. Mono- and disulfur bridges are established, and the new dyestuff molecules were studied with respect to their structural, optical, and el
- Ahrens, Johannes,Boeker, Birte,Brandhorst, Kai,Funk, Markus,Broering, Martin
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p. 11382 - 11395
(2013/09/02)
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- Catalytic thia-Sommelet-Hauser rearrangement: Application to the synthesis of oxindoles
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A series of 3-arylthio-1,3-disubstituted-oxindoles were prepared in good yields by the reaction of α-diazocarbonyl compounds and sulfenamides. The reaction involves a Rh-catalyzed thia-Sommelet-Hauser-type rearrangement.(Figure Presented)
- Li, Yuye,Shi, Yi,Huang, Zhongxing,Wu, Xinhu,Xu, Pengfei,Wang, Jianbo,Zhang, Yan
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supporting information; experimental part
p. 1210 - 1213
(2011/04/27)
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- CYSTEINE AND CYSTINE PRODRUGS TO TREAT SCHIZOPHRENIA AND REDUCE DRUG CRAVINGS
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The present invention provides cysteine and cystine prodrugs for the treatment of schizophrenia and drug addiction. The invention further encompasses pharmaceutical compositions containing prodrugs and methods of using the prodrugs and compositions for treatment of schizophrenia and drug addiction.
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Page/Page column 26-27
(2009/10/09)
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- Reactions of phosphate and phosphorothiolate diesters with nucleophiles: Comparison of transition state structures
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A series of methyl aryl phosphorothiolate esters (SP) were synthesized and their reactions with pyridine derivatives were compared to those for methyl aryl phosphate esters (OP). Results show that SP esters react with pyridine nucleophiles via a concerted SN2(P) mechanism. Bronsted analysis suggests that reactions of both SP and OP esters proceed via transition states with dissociative character. The overall similarity of the transition state structures supports the use of phosphorothiolates as substrate analogues to probe mechanisms of enzyme-catalyzed phosphoryl transfer reactions. This journal is The Royal Society of Chemistry.
- Ye, Jing-Dong,Barth, Christofer D.,Anjaneyulu, Potluri S. R.,Tuschl, Thomas,Piccirilli, Joseph A.
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p. 2491 - 2497
(2008/02/14)
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- Iterative one-pot synthesis of oligosaccharides
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Straight to the point! Preactivation of a p-tolyl thioglycoside donor, followed by sequential addition of p-tolyl thioglycosyl acceptors in one reaction flask allowed rapid syntheses of oligosaccharides independent of anomeric reactivities of donors and a
- Huang, Xuefei,Huang, Lijun,Wang, Haisheng,Ye, Xin-Shan
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p. 5221 - 5224
(2007/10/03)
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- Mechanism of the second sulfenylation of indole
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Sulfenylation of indole using a sulfenyl chloride occurs initially at the 3-position of the ring, leading to a 3-indolyl sulfide. When an excess of sulfenyl chloride is used, a second sulfide group is introduced at the 2-position, and an indolyl 2,3-bis-sulfide results. We have demonstrated that this second sulfenylation occurs not by direct introduction of the second sulfide at the 2-position but via initial formation of an indolenium 3,3-bis-sulfide intermediate, followed by migration of one of the sulfide groups to the 2-position. This was achieved by the isolation of two examples of 3H-indole 3,3-bis-sulfides and by subsequent demonstration that they rearrange to the indolyl 2,3-bis-sulfides by treatment with sulfenyl halides.
- Hamel, Pierre
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p. 2854 - 2858
(2007/10/03)
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- Synthesis of sulfides of the azulene series by reaction of chamazulene with sulfenyl chlorides
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Sulfides of the azulene series were synthesized in high yield by reactions of chamazulene (7-ethyl-1,4-dimethylazulene) with aliphatic, aromatic, and heterocyclic sulfenyl chlorides. According to the 1H NMR and X-ray diffraction data, electrophilic substitution by RS+ cation occurs exclusively at the C3 atom of the azulene system.
- Palei,Plemenkov,Lodochnikova,Kataeva,Litvinov
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p. 1717 - 1721
(2007/10/03)
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- The use of tert-Butyl vinyl ether in stepwise electrophllic addition reactions
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tert-Butyl vinyl ether (1) reacts with p-TolSCl to give 2-tert-butoxy-2-chloroethyl p-tolyl sulfide (2). In the presence of SnCl4, 2 reacts with silyl enol ethers, allyltrimethylsilane, and vinyl ethers to form a C-C bond. In the case of vinyl ethers, the reaction proceeds through the formation of the 5-membered sulfonium salt intermediate which in turn can react with H2O, TMSCN, allyltrimethylsilane, and Grignard reagents.
- Koikov, Leonid N.,Han, Mingming,Wellman, Dawn M.,Kelly, Jim A.,Smoliakova, Irina P.
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p. 3451 - 3464
(2007/10/03)
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- The kinetics and mechanism of the reaction of tricoordinate phosphorus compounds with sulfenate esters
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The kinetics and mechanism of the reaction of tricoordinate phosphorus compounds, ArnP(OCH2CF3)3-n with arylsulfenate esters, ArSOCH2CF3, are reported. Product analysis, kinetic order, activation parameters, Hammett data and solvent effects are the criteria used to elucidate the two step mechanism involving arylthiophosphoranes as intermediates.
- Hall, C. Dennis,Tweedy, Bruce R.,Lowther, Nicholas
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p. 341 - 358
(2007/10/03)
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- Tandem sequence of ArSCl initiated AdE reactions resulting in formation of two C-C bonds
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A one-pot procedure for the sequence of reactions between arylsulfanyl chloride, vinyl ether-I, vinyl ether-II and organomagnesium reagents has been developed for assembling polyfunctional compounds from simple precursors. 2,3-Dihydropyran and various vin
- Smoliakova, Irina P.,Caple, Ron,Magnuson, Vincent R.,Polyakov, Valery R.,Smit, William A.,et al.
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p. 1065 - 1070
(2007/10/02)
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- Convenient One-Pot Synthesis of Sulfonyl Chlorides from Thiols Using Sulfuryl Chloride and Metal Nitrate
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Various sulfonyl chlorides were obtained in excellent yields by the reaction of alkyl and aryl thiols with sulfuryl chloride in the presence of metal nitrate under mild condition in aprotic solvents such as acetonitrile and N,N-dimethylformamide.
- Park, Young Jun,Shin, Hyun Ho,Kim, Yong Hae
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p. 1483 - 1486
(2007/10/02)
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- Structural Effects on -Sigmatropic Hydrogen Shifts of Vinylallenes
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This study was directed toward developing a more quantitative understanding of ring size and sulfoxide anti-directing effects on the reactivity profile and/or stereochemical course of -sigmatropic hydrogen shifts of vinylallenes.Regarding ring size effects, vinylallenes 13a-c were synthesized and subjected to kinetic studies.The results were not in simple agreement with an earlier prediction from this laboratory that the ring size which influences the migrating hydrogen trajectory distance is the primary determinant in the rate of vinylallene isomerization to hexatrienes.It is apparent that additional factors such as ring strain have to be taken into account.Regarding substituent effects on the ?-facial stereochemical course of -shifts, vinylallenes with various terminal allenic substituents were studied and it is concluded that the anti-directing effect imparted by a sulfoxide group and enhancement of this effect by a geminal alkyl substituent are general.Of all the substituents studied previously and in this investigation (alkyl, sulfide, sulfoxide, sulfone, phosphine oxide, phosphonate, and carbonyl), the sulfoxide remains the only substituent which imparts significant ?-facial selectivity.
- Wu, Kuo-Ming,Midland, M. Mark,Okamura, William H.
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p. 4381 - 4392
(2007/10/02)
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- Cyclofunctionalization of 2-Allyl-phenols with Sulfur Chlorides. III. 2-Arylthiomethyl-2,3-dihydrofuroquinolins from 7-Allyl- and 7-Methallyl-8-hydroxyquinoline, respectively, and Arylsulfenyl Chlorides
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Reactions of 7-allyl- (3) and 7-methallyl-8-hydroxyquinoline (4) with selected arylsulfenyl chlorides (5a-d) yield the products of cyclofunctionalization corresponding 2-arylthiomethyl-2,3-dihydrofuroquinolins (6 and 7).The products are identified by 1H-n.m.r.-spectroscopy, mass spectrometry and microanalysis.
- Meinhold, H.,Muehlstaedt, M.,Muslih, R. M.
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p. 136 - 140
(2007/10/02)
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- Fluorinated Tertiary Thio- and Selenoethers from the Reaction of Sulfenyl or Selenenyl Chloride with Perfluoropropene Dimers in the Presence of Alkali Fluoride
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Perfluoro(1,1-dimethylbutanide) anion generated from hexafluoropropene dimers and alkali fluorides in dry N,N-dimethylformamide, reacts with arenesulfenyl or areneselenenyl chloride to give the corresponding aryl perfluoro(1,1-dimethylbutyl) sulfides or selenides in low to good yields.
- Suzuki, Hitomi,Satake, Hiroshi,Uno, Hidemitsu,Shimizu, Hiroaki
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p. 4471 - 4473
(2007/10/02)
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- The Reaction of 9-(2',3'-Dideoxy-β-D-glycero-pent-2-Enofuranosyl)-adenine Derivatives with Arene- and Alkenesulfenyl Chlorides. An Unusual Ring Opening Reaction of Thiiranium Ions
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A series of arenesulfenyl chlorides and methanesulfenyl chloride were reacted in pyridine solution with 6-N-dibenzoyl-9-(2',3'-dideoxy-β-D-glycero-pent-2-enofuranosyl)adenine (1b).In each case, the relative abundance of isomeric β-chloroarene/alkene sulfides was estimated and used to assess the relative thermodynamic stabilities of the lyxo and ribo thiiranium ion intermediates and their steric susceptibilities to attack by nucleophile (Cl-).Subsequently, the β-chloroarene/alkene sulfides 8a-d to 13 a-d, upon alkaline treatment, underwent an unprecedented ylide-mediated β elimination of the intermediary lyxo and ribo thiiranium ions, to give only 2'-ene-thiol ethers 14-19.
- Welch, C. J.,Bazin, H.,Chattopadhyaya, J.
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p. 343 - 357
(2007/10/02)
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- Antidiabetic pyrrolecarboxylic acids
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Certain pyrrolecarboxylic and pyrroleacetic acid derivatives substituted on the pyrrole ring with thioether groups, acyl groups, phenyl, substituted phenyl, phenoxy, substituted phenoxy, benzyl or halo and optionally substituted on the pyrrole nitrogen with alkyl, and the pharmaceutically acceptable salts thereof, are useful in lowering the blood glucose levels of hyperglycemic animals.
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- Antidiabetic furancarboxylic and thiphenecarboxylic acids
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Compounds of the structure STR1 wherein Z is oxygen or sulfur; R is (C1 -C2)alkoxy; phenoxy; benzyl; phenylthiomethyl; phenylthio; phenylthio monosubstituted in the 2-, 3- or 4-position with (C1 -C3)alkyl, pheny
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- SULFENYL CHLORIDES, XIV; THE REACTION OF ARYLTHIOSULFONATES WITH ARYLSULFENYL HALIDES
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Utilizing partial results published earlier , the sulfenylation reaction of aromatic thiolsulfonates was investigated.Aromatic thiolsulfonates rapidly react with sulfenyl bromide in acetonitrile solution, whereas with sulfenyl chloride the splitting of the thiolsulfonate bond proceeds only in dimethylformamide and under forceful conditions.
- Lazar, J.,Vinkler, E.
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p. 171 - 174
(2007/10/02)
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- Silicon in Synthesis. 8. Vinyltrimethylsilane, a Convenient Ethylene Equivalent for the Synthesis of Vinyl Aryl Sulfides, Vinyl Aryl Sulfoxides, Thiosilylketene Acetals, and Fused Cyclopentenones
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Vinyltrimethylsilane reacts with a variety of arylsulfenyl chlorides to give 2-chloro-1-(trimethylsilyl)ethyl aryl sulfide adducts 9-13.These adducts can be converted into vinyl aryl sulfides and vinyl aryl sulfoxides, and for the case of 2-chloro-1-(trimethylsilyl)ethyl phenyl sulfide (11), treatment with 1,5-diazabicyclonon-5-ene (DBN) gave 1-(trimethylsilyl)-1-(phenylthio)ethylene (24). α,β-Unsaturated acid chlorides react with vinyltrimethylsilane in the presence of stannic tetrachloride to give fused cyclopentenones.In all of the reaction described, vinyltrimethylsilane serves as a convenient ethylene equivalent.
- Cooke, Frank,Moerck, Rudi,Schwindeman, James,Magnus, Phillip
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p. 1046 - 1053
(2007/10/02)
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- Electrophilic additions to allenes. VI. The role of steric versus electronic effects in the reactions of arenesulphenyl halides with allenes
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The role of steric and electronic effects during the rate and product determining steps for the addition of arenesulphenyl chlorides to 1,3-disubstituted allenes has been briefly examined.Both effects appear to be generally of minimal importance during the rate determinig step.The available rate data indicate the presence of little, if any, build up of positive charge on sulphur.These results are interpreted in terms of an SN2 attack on bivalent sulphur leading to an alkylidenethiiranium ion intermediate.Steric effects are of greater importance in the product determinig step, particularly when the sulphenyl chlorides possess two bulky ortho substituents, as in the case of 2,4,6-triisopropylbenzenesulphenyl chloride.
- Garratt, Dennis G.,Beaulieu, Pierre L.
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p. 2738 - 2744
(2007/10/02)
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- Reaction of Phosphinyl and Phosphinothioyl Disulfides with Diazomethane
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Four kinds of 4-substituted phenyl diethoxyphosphinyl disulfide (substituents: H, CH3, C2H5, Cl) and phenyl diethoxyphosphinothioyl disulfide reacted readily with diazomethane.The phosphinyl disulfides produced diethyl (4-substituted phenylthio)methyl phosphorothionate and the isomer, diethyl S-(4-substituted phenylthio)methyl phosphorothiolate, as the main products, whereas the phosphinothioyl disulfide produced only diethyl S-(phenylthio)methyl phosphorodithioate.The possible mechanism involved is as follows: the S-S bond in (EtO)2P(X)-S-S-C6H4R (X=O or S) is cleaved by nucleophilic attack of diazomethane at the sulfur atom bonded to the phenyl group to produce and (+)N2CH2-S-C6H4R; the latter reacts with the former with loss of nitrogen; therefore, when X is O, two compounds, (EtO)2P(S)-O-CH2-S-C6H4R and (EtO)2P(O)-S-CH2-S-C6H4R, are produced, when X is S, only (EtO)2P(S)-S-CH2-S-C6H4R is obtained.
- Miyamoto, Toru,Yamamoto, Izuru
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p. 2581 - 2586
(2007/10/02)
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