- Copper-catalyzed aerobic oxidative cross-coupling reactions of vinylarenes with sulfinate salts: A direct approach to β-ketosulfones
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A copper-catalyzed aerobic oxidative cross-coupling reactions for the synthesis of β-ketosulfones via formation of a C[sbnd]S bond has been demonstrated. Promoted by the crucial copper catalyst, perfect selectivity and good to excellent yields could be achieved. This method, including inexpensive copper catalyst, wide functional group tolerance, and open air conditions, make it very attractive and practical. More importantly, it also provides a versatile tool for the construction of β-ketosulfones from basic starting materials under mild conditions.
- Chen, Yu,Xu, Lei,Wang, Biyu,Jiang, Jingjing,Sun, Yixiang,Li, Longchun
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- Visible-light-promoted aerobic oxidative synthesis of β-ketosulfones under photocatalyst-free conditions
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A simple and convenient visible-light-mediated method has been developed for the construction of β-ketosulfones via aerobic oxidative difunctionalization of alkynes with arylazo sulfones and dioxygen in air under photocatalyst-free conditions. The present photochemical methodology provides a facile and attractive protocol to construct a series of β-ketosulfones in moderate to good yields.
- Lv, Yufen,Liu, Qishun,Liu, Fei,Yue, Huilan,Li, Jiang-Sheng,Wei, Wei
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supporting information
(2019/11/26)
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- Synthesis of β-ketosulfone derivatives as new non-cytotoxic urease inhibitors in vitro
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Background: Peptic ulcer and urolithiasis are largely due to infection caused by urease-producing bacteria. Therefore, the discovery of urease inhibitors is an important area of medicinal chemistry research. Objective: The main aim of the work was to identify novel urease inhibitors with no cytotoxicity. Method: During the current study, a series of β-ketosulfones 1-26 was synthesized in two steps and evaluated for their in vitro urease inhibition potential. Results: Out of twenty-six compounds, seventeen have shown good to significant urease inhibitory activity with IC50 values ranging between 49.93-351.46 μM, in comparison to standard thiourea (IC50 = 21 ± 0.11 μM). Moreover, all compounds found to be non-cytotoxic against normal 3T3 cell line. Conclusion: This study has identified β-ketosulfones as novel and non-cytotoxic urease inhibitors.
- Iqbal Choudhary, M.,Iqbal, Sarosh,Khan, Ajmal,Khan, Khalid Mohammed,Kiran, Shumaila,Nazir, Rashid,Perveen, Shahnaz
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p. 244 - 255
(2020/03/10)
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- Preparation method of beta-carbonyl sulfone compound promoted by visible light
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The invention discloses a preparation method of a beta-carbonyl sulfone compound promoted by visible light. The preparation method includes the following steps that olefin and aryl-sulphonazo are mixed with an organic solvent and water, and then a reaction is conducted for 16-24 hours at room temperature under visible illumination; and after the reaction, ethyl acetate is used for extracting reaction liquid, and the beta-carbonyl sulfone compound is obtained after concentration and column chromatography isolation of an extract. According to the method, clean light energy is used as reaction energy, oxygen in air is used as an oxidant and an oxygen source, the beta-carbonyl sulfone compound is effectively synthesized at the room temperature, the method does not require any photocatalyst orequivalent inorganic oxidant, and has the advantages of easy and convenient operation, low energy consumption, high reaction safety, environmental friendliness and the like.
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Paragraph 0056-0059
(2019/11/13)
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- Photocatalyst-Free Visible Light-Induced Synthesis of β-Oxo Sulfones via Oxysulfonylation of Alkenes with Arylazo Sulfones and Dioxygen in Air
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A catalyst-free strategy has been established for the synthesis of β-oxo sulfones via visible light-induced oxysulfonylation of alkenes with arylazo sulfones with dioxygen in air. The present photoinduced transformation proceeds smoothly at room temperature in the absence of an external photosensitizer, which not only provides a mild and efficient approach to various β-oxo sulfones, but also opens a different reaction mode for the photochemical reaction of arylazo sulfones.
- Liu, Qishun,Liu, Fei,Yue, Huilan,Zhao, Xiaohui,Li, Jiangsheng,Wei, Wei
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supporting information
p. 5277 - 5282
(2019/11/16)
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- Efficient synthesis of chiral β-hydroxy sulfones: Via iridium-catalyzed hydrogenation
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A highly efficient Ir/f-Amphol-catalyzed asymmetric hydrogenation of prochiral β-keto sulfones was successfully developed to prepare a series of chiral β-hydroxy sulfones with good to excellent results (62%->99% conversions, 35%-99% yields and 86%->99% ee). Our Ir/f-Amphol L4 catalytic system exhibited very high activity; the gram-scale asymmetric hydrogenation was performed well with just 0.005 mol% catalyst loading (S/C = 20,000) to afford the desired product 2a with >99% conversion, 99% yield and 93% ee.
- Tao, Lin,Yin, Congcong,Dong, Xiu-Qin,Zhang, Xumu
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supporting information
p. 785 - 788
(2019/01/30)
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- Facile Synthesis of β-Keto Sulfones Employing Fenton's Reagent in DMSO
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A new facile method for the synthesis of β-keto sulfones employing xanthates, DMSO, and Fenton's reagent is described. The reaction proceeds under very mild conditions providing a cost-effective straightforward approach to various β-keto sulfones in high yields.
- Chalikidi, Petrakis N.,Uchuskin, Maxim G.,Trushkov, Igor V.,Abaev, Vladimir T.,Serdyuk, Olga V.
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supporting information
p. 571 - 575
(2018/01/11)
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- Nickel-Catalyzed Highly Enantioselective Hydrogenation of β-Acetylamino Vinylsulfones: Access to Chiral β-Amido Sulfones
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The nickel/(S)-Binapine complex was found to be an efficient catalyst for asymmetric hydrogenation of β-acetylamino vinylsulfones to afford chiral β-Amido sulfones with excellent yields and enantioselectivities (up to 95% yields and >99% ee). This protocol has good compatibility with a series of substituted (Z)-β-acetylamino vinylsulfones or Z/E isomeric mixtures. A gram-scale reaction has also been achieved in the presence of a 0.2 mol % catalyst loading.
- Long, Jiao,Gao, Wenchao,Guan, Yuqing,Lv, Hui,Zhang, Xumu
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supporting information
p. 5914 - 5917
(2018/09/25)
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- CO/O2 assisted oxidative carbon-carbon and carbon-heteroatom bond cleavage for the synthesis of oxosulfonates from DMSO and olefins
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Selective carbon-carbon and carbon-heteroatom bond cleavage was achieved in a one reaction system. With this strategy a novel Pd/Cu-catalyzed aerobic oxidative oxosulfonation of olefins with DMSO has been developed. Preliminary mechanistic investigations indicated that CO/O2 assisted the bond cleavage and the leaving groups from the starting materials were trapped by O2 and underwent a hydroxylation process.
- Shao, Ailong,Gao, Meng,Chen, Songtao,Wang, Tao,Lei, Aiwen
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p. 2175 - 2178
(2017/03/09)
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- Iron(III)-catalyzed aerobic oxidation and cleavage/formation of a C-S bond
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A new iron(III)-catalyzed synthesis of β-oxo sulfones is described that employs vinylarenes and readily available dimethyl sulfoxide (DMSO) with hydrazine and oxygen as the oxidant. The reaction tolerates various functional group substituents on the vinylarene substrates to afford β-oxo sulfones in moderate to good yields. The cleavage and formation of the C-S bond are the key steps of this transformation.
- Shi, Xiaokang,Ren, Xiaoyu,Ren, Zhiyong,Li, Jian,Wang, Yuling,Yang, Sizhuo,Gu, Jixiang,Gao, Qiang,Huang, Guosheng
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supporting information
p. 5083 - 5088
(2014/08/18)
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- Catalytic and direct methyl sulfonylation of alkenes and alkynes using a methyl sulfonyl radical generated from a DMSO, dioxygen and copper system
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This paper describes an efficient method to β-keto methyl sulfones and (E)-vinyl methyl sulfones using DMSO as the substrate. The methyl sulfonyl radical generated from DMSO in the presence of catalytic Cu(i) under O2 atmosphere is believed to be involved in this reaction. Isotopic labeling and 18O2 experiments were performed to investigate the reaction mechanism.
- Jiang, Yaojia,Loh, Teck-Peng
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p. 4939 - 4943
(2015/01/09)
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- L-proline-catalyzed three-component domino [3+2+1] annulation for the regio- and diastereoselective synthesis of highly substituted thienothiopyrans containing three or four stereocenters
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(Chemical Equation Presented) L-Proline-catalyzed three-component reactions of ethyl 2-[(2-oxo-2-arylethyl)sulfonyl]acetate or ethyl 2-[(2-ethoxy-2- oxoethyl)sulfonyl]acetate, aromatic aldehydes, and 5-aryltetrahydro-3- thiophenone furnished a variety of highly substituted thieno[3,2-c]thiopyran derivatives. This facile transformation presumably occurs via a one-pot domino sequence of enamine formation/aldol condensation/Michael addition/6-exo-trig cyclization/elimination and involves the creation in a single operation of three C-C bonds and the generation of three new stereocenters with complete diastereoselectivity in all cases and a fourth one in ca. 7:3 diastereomeric ratio when starting from a 5-substituted tetrahydro-3-thiophenone derivative.
- Indumathi, Sethuraman,Perumal, Subbu,Menendez, J. Carlos
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scheme or table
p. 472 - 475
(2010/03/25)
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- Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)- 3(trifluoromethyl)-1h-pyrazol-1-yl]benzenesulfonamide (sc-58635, celecoxib)
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A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC- 236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of 1i (4-[5-(4-methylphenyl)-3- (trifluoromethyl)-1H-pyrazol-1-y1]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.
- Penning, Thomas D.,Talley, John J.,Bertenshaw, Stephen R.,Carter, Jeffery S.,Collins, Paul W.,Docter, Stephen,Graneto, Matthew J.,Lee, Len F.,Malecha, James W.,Miyashiro, Julie M.,Rogers, Roland S.,Rogier,Yu, Stella S.,Anderson, Gary D.,Burton, Earl G.,Cogburn, J. Nita,Gregory, Susan A.,Koboldt, Carol M.,Perkins, William E.,Seibert, Karen,Veenhuizen, Amy W.,Zhang, Yan Y.,Isakson, Peter C.
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p. 1347 - 1365
(2007/10/03)
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- Reactions of sulfonyl chlorides with silyl enol ethers catalysed by a ruthenium(II) phosphine complex: Convenient synthesis of β-keto sulfones
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The reactions of alkane- and arene-sulfonyl chlorides with silyl enol ethers in the presence of a ruthenium(II) phosphine complex are found to give β-keto sulfones in good to high yields.
- Kamigata, Nobumasa,Udodaira, Kumiko,Shimizu, Toshio
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p. 783 - 786
(2007/10/03)
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