- An aryl thiol-vinyl azide coupling reaction and a thiol-vinyl azide coupling/cyclization cascade: efficient synthesis of β-ketosulfides and arene-fused 5-methylene-2-pyrrolidinone derivatives
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The addition reaction of thiol to vinyl azide has been extensively studied. Variously substituted aryl thiols are all viable for this coupling process. The scope of the other partner is successfully expanded from α-aryl vinyl azide to α-alkyl vinyl azide.
- Wang, Yong,Wang, Yu-Jiao,Liang, Xian-Chen,Shen, Mei-Hua,Xu, Hua-Dong,Xu, Defeng
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p. 5169 - 5176
(2021/06/21)
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- Iridium-Catalyzed Carbenoid Insertion of Sulfoxonium Ylides for Synthesis of Quinoxalines and β-Keto Thioethers in Water
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Sulfoxonium ylides as safe carbene precursors are described for iridium-catalyzed carbene insertions and annulation, providing a facile and green approach to access a variety of quinoxaline derivatives in water. This water-mediated method also allows the preparation of β-keto thioethers under mild condition.
- Xu, Yingying,Huang, Xin,Lv, Guanghui,Lai, Ruizhi,Lv, Songyang,Li, Jianglian,Hai, Li,Wu, Yong
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p. 4635 - 4638
(2020/07/04)
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- Substituted α-Sulfur Methyl Carbanions: Effective Homologating Agents for the Chemoselective Preparation of β-Oxo Thioethers from Weinreb Amides
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The proper generation of α-thiomethyllithium reagents via reductive lithiation or deprotonation followed by reaction with variously functionalized Weinreb amides represents an excellent method to access β-oxo thioethers. The procedure is adaptable to alky
- Senatore, Raffaele,Ielo, Laura,Urban, Ernst,Holzer, Wolfgang,Pace, Vittorio
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supporting information
p. 2466 - 2470
(2018/05/03)
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- KI/K 2 S 2 O 8 -Mediated α-C-H Sulfenylation of Carbonyl Compounds with (Hetero)Aryl Thiols
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A new and facile KI/K 2 S 2 O 8 -mediated α-C-H sulfenylation of carbonyl compounds with (hetero)aryl thiols was developed for the formation of C-S bond at room temperature. This method provided a simple process for the sy
- Yang, Zan,Li, Jiao,Hua, Jie,Yang, Tao,Yi, Jianmin,Zhou, Congshan
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supporting information
p. 2325 - 2329
(2017/10/06)
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- Catalyst-Free Insertion of Sulfoxonium Ylides into Aryl Thiols. A Direct Preparation of β-Keto Thioethers
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Insertion of sulfoxonium ylides into the S-H bond of aryl thiols without the need for a catalyst is demonstrated, furnishing β-keto thioethers in excellent yield in most cases. The method overcomes traditional syntheses that employ metal catalysts in combination with diazo compounds or toxic and hard-prepared haloketones. The experimental setup consists of mixing the reagents in acetonitrile at room temperature. Additional experimental as well as kinetic isotopic effect studies give some insight into the mechanism of this reaction.
- Dias, Rafael M. P.,Burtoloso, Antonio C. B.
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p. 3034 - 3037
(2016/07/06)
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- Catalyst-Free Difunctionalization of Activated Alkenes in Water: Efficient Synthesis of β-Keto Sulfides and Sulfones
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Difunctionalization of activated alkenes, a powerful strategy in chemical synthesis, has been accomplished for direct synthesis of a series of β-keto sulfides and β-keto sulfones. The transformation, mediated by O2, proceeds smoothly in water and without any catalyst. Prominent advantages of this method include mild reaction conditions, purification simplicity, and gram-scale synthesis, underlining the practical utility of this methodology.
- Wang, Huamin,Wang, Guangyu,Lu, Qingquan,Chiang, Chien-Wei,Peng, Pan,Zhou, Jiufu,Lei, Aiwen
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p. 14489 - 14493
(2016/10/03)
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- Copper-Catalyzed Synthesis of α-Thioaryl Carbonyl Compounds Through S-S and C-C Bond Cleavage
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A method to access α-thioaryl ketones and α-thioaryl esters employing copper acetate (hydrate) as catalyst and readily accessible diaryl disulfides and β-diketones (or β-keto esters) has been developed. Both alkyl- and aryl-substituted carbonyl compounds can be prepared. Copyright
- Zou, Liang-Hua,Priebbenow, Daniel L.,Wang, Long,Mottweiler, Jakob,Bolm, Carsten
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supporting information
p. 2558 - 2563
(2013/10/21)
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- ALLOSTERIC PROTEIN KINASE MODULATORS
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The invention provides specific small molecule compounds that allosterically regulate the activity or modulate protein-protein interactions of AGC protein kinases and the Aurora family of protein kinases, methods for their production, pharmaceutical compositions comprising same, and their use for preparing medicaments for the treatment and prevention of diseases related to abnormal activities of AGC protein kinases or of protein kinases of the Aurora family.
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Page/Page column 70
(2012/03/10)
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- Gold-catalyzed carbene transfer to alkynes: Access to 2,4-disubstituted furans
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Furans of gold: The first example of a gold-catalyzed intermolecular addition of carbon ylides to terminal alkynes is reported (see scheme; DCE=dichloroethane, Tf=trifluoromethanesulfonyl). Subsequent intramolecular trapping of the generated gold carbene completes a formal [3+2] cycloaddition, which represents a novel synthesis of 2,4-disubstituted furans. Copyright
- Kramer, Soren,Skrydstrup, Troels
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supporting information; experimental part
p. 4681 - 4684
(2012/06/30)
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- Selective one-pot multicomponent synthesis and anti-tubercular evaluation of 5-(aryl/cyclohexylsulfanyl)-2-alkoxy-4,6-diarylnicotinonitriles
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A new set of highly substituted pyridine derivatives has been synthesized by a product selective four component reaction of aryl aldehyde, malononitrile and 2-aryl/cyclohexylsulfanyl-1-aryl-1-ethanones in presence of sodium hydroxide in methyl/ethyl alcoh
- Manikannan, Ramaiyan,Muthusubramanian, Shanmugam,Yogeeswari, Perumal,Sriram, Dharmarajan
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supporting information; experimental part
p. 3352 - 3355
(2010/08/07)
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- Pyrazole derivatives from azines of substituted phenacyl aryl/cyclohexyl sulfides and their antimycobacterial activity
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Azines derived from substituted phenacyl aryl/cyclohexyl sulfide on treatment with excess phosphorous oxychloride in N,N-dimethylformamide have been found to yield two isomeric pyrazoles in each case. A plausible mechanism has been suggested for the forma
- Manikannan, Ramaiyan,Venkatesan, Ramaiyan,Muthusubramanian, Shanmugam,Yogeeswari, Perumal,Sriram, Dharmarajan
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supporting information; experimental part
p. 6920 - 6924
(2011/02/22)
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- 3,5-Diphenylpent-2-enoic acids as allosteric activators of the protein kinase PDK1: Structure-activity relationships and thermodynamic characterization of binding as paradigms for PIF-binding pocket-targeting compounds
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The modulation of protein kinase activities by low molecular weight compounds is a major goal of current pharmaceutical developments. In this line, important efforts are directed to the development of drugs targeting the conserved ATP binding site. Howeve
- Stroba, Adriana,Schaeffer, Francis,Hindie, Valerie,Lopez-Garcia, Laura,Adrian, Iris,Fr?hner, Wolfgang,Hartmann, Rolf W.,Biondi, Ricardo M.,Engel, Matthias
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supporting information; experimental part
p. 4683 - 4693
(2010/02/28)
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- Novel N,S-phenacyl protecting group and its application for peptide synthesis
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The phenacyl group can be introduced onto amino and thio groups by N,S-alkylation reactions. Conversely, these groups are removed rapidly by employing magnesium in acetic acid. This protecting group was successfully applied to a short peptide synthesis of Boc-L-Cys-Gly-OMe. Georg Thieme Verlag Stuttgart.
- Tang, Guo,Ji, Tao,Hu, An-Fu,Zhao, Yu-Fen
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experimental part
p. 1907 - 1909
(2009/04/11)
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- Structure-activity relationship of antileishmanials neolignan analogues
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Twenty-two synthetic analogues of neolignans comprising β-ketoethers and β-ketosulfides were obtained from condensation reactions among β-bromoketones and phenols or thiophenols, respectively, in basic solutions, and assayed in vitro for activity against
- Aveniente, Mario,Pinto, Eduardo F.,Santos, Lourivaldo S.,Rossi-Bergmann, Bartira,Barata, Lauro E.S.
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p. 7337 - 7343
(2008/04/05)
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- Sulfite-promoted one-pot synthesis of sulfides by reaction of aryl disulfides with alkyl halides
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A sodium dithionite, sodium thiosulfate and rongalite promoted one-pot synthesis of aryl alkyl sulfides at room temperature has been developed. The reactions of a range of disulfides with alkyl halides proceeded smoothly in the presence of rongalite. Possible reaction pathways are discussed and the effects of these sulfites on disulfides are investigated. The important features of this protocol are metal-free, strong-base-free, and mild reaction conditions, operational simplicity, short reaction times and high yields of products. Georg Thieme Verlag Stuttgart.
- Tang, Ri-Yuan,Zhong, Ping,Lin, Qiu-Lian
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- One-pot synthesis of sulfides by reaction of disulfides with alkyl halides in the presence of sodium dithionite
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Sodium dithionite-promoted synthesis of unsymmetrical diorganyl sulfides by a reaction of diaryl disulfides with alkyl halides at r.t. has been developed. The advantages offered by this method are operational simplicity, a faster reaction, neutral and mild reaction conditions, and moderate to good yields of products.
- Tang, Ri-Yuan,Zhong, Ping,Lin, Qiu-Lian
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p. 167 - 174
(2007/10/03)
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- Enolate Structures Contributing to the Transition State for Nucleophilic Substitution on α-Substituted Carbonyl Compounds
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The high SN2 reactivity of α-halocarbonyl compounds is explained by the lowering of the intrinsic barrier by a major contribution of enolate structure to the transition state.This theoretical conclusion is now shown experimentally.The evidence is as follows: (1) Change in structure of a leaving arenesulfonate ion does not change the rates of attack of benzenesulfonate ion by nearly as much as it changes the equilibrium constants.A charge on the transferring phenacyl group of -0.48 is deduced. (2) The ρ value (-3.9) for attack of substituted thiophenoxides on phenacyl bromide is much more negative than that for attack on methyl iodide (-1.8). (3) A related ρ value is found for reaction of 2,4,6-trimethylphenacyl bromide with thiophenoxides (-2.2), showing a lesser, but still large sensitivity to nucleophile structure where addition to the carbonyl is sterically forbidden.The enolate structure leaves the attacking or leaving nucleophiles with a single electron each instead of the unshared pairs.Thus, the enolate structure is emphesized if the leaving group and the nucleophile readily lose an electron.
- Yousaf, T. I.,Lewis, E. S.
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p. 6137 - 6142
(2007/10/02)
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- Kinetic Study on the Reaction of (Arylthio)trimethylsilanes with Phenacyl Bromide Giving Aryl Phenacyl Sulfides and Bromotrimethylsilane
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A kinetic study has been conducted on the reactions of (arylthio)trimethylsilanes with phenacyl bromide giving aryl phenacyl sulfides and bromotrimethylsilane.Remarkably large positive substituent effect (ρ=+2.2) and large negative entropy of activation were obsrved for the reaction.A mechanism involving 5-coordinated silicon intermediate prior to the rate-determining heterolysis of the Si-S bond has been suggested for the reaction based on the kinetic results.
- Kozuka, Seizi,Higashino, Tetsuji,Kitamura, Takuro
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p. 1420 - 1423
(2007/10/02)
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