- Selective C-C bonds formation, N-alkylation and benzo[d]imidazoles synthesis by a recyclable zinc composite
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Earth abundant metals are much less expensive, promising, valuable metals and could be served as catalysts for the borrowing hydrogen reaction, dehydrogenation and heterocycles synthesis, instead of noble metals. The uniformly dispersed zinc composites were designed, synthesized and carefully characterized by means of XPS, EDS, TEM and XRD. The resulting zinc composite showed good catalytic activity for the N-alkylation of amines with amines, ketones with alcohols in water under base-free conditions, while unsaturated carbonyl compounds could also be synthesized by tuning the reaction conditions. Importantly, it was the first time to realize the synthesis of 2-aryl-1H-benzo[d]imidazole derivatives by using this zinc composite under green conditions. Meanwhile, this zinc catalyst could be easily recovered and reused for at least five times.
- Zhu, Guanxin,Duan, Zheng-Chao,Zhu, Haiyan,Ye, Dongdong,Wang, Dawei
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supporting information
p. 266 - 270
(2021/08/06)
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- Annulative Morita-Baylis-Hillman reaction to synthesise chiral dibenzocycloheptanes
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We describe the first metal-free and organocatalytic strategy to access highly functionalised dibenzocycloheptanesviaa phosphine-promoted annulative Morita-Baylis-Hillman (MBH) reaction. The method is manipulated to access to chiral dibenzocycloheptanes as well. This work represents a rare entry for the construction of seven-membered carbocyclesviathe MBH route. The realisation of several bioactive molecules possessing the dibenzocycloheptane core makes this an attractive strategy.
- Mondal, Atanu,Ramasastry, S. S. V.,Shivangi,Tung, Pinku,Wagulde, Siddhant V.
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supporting information
p. 9260 - 9263
(2021/09/20)
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- Iridium and copper supported on silicon dioxide as chemoselective catalysts for dehydrogenation and borrowing hydrogen reactions
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High active ligand usually plays an important role during catalysis and synthesis chemistry. A new and efficient benzotriazole-pyridinyl-silane ligand (BPS) was designed, and the corresponding iridium and copper catalysts were synthesized and thoroughly characterized by means of EDS, TEM, and XPS. The resulting iridium composite revealed excellent catalytic activity for the reaction of tert-butanesulfinamide with benzyl alcohols, while copper catalyst could realize the synthesis of unsaturated carbonyl compounds through the reaction of benzyl alcohols with ketones. This provided an efficient method for selective synthesis of unsaturated carbonyl compounds from benzyl alcohols and ketones in high yields with good recovery performance.
- Zhu, Guanxin,Duan, Zheng-Chao,Zhu, Haiyan,Qi, Minghui,Wang, Dawei
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- Hydroxyl- and Halogen-containing Chalcones for the Inhibition of LPS-stimulated ROS Production in RAW 264.7 Macrophages: Design, Synthesis and Structure–Activity Relationship Study
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Oxidative stress due to overproduction of reactive oxygen species (ROS) plays a major role in inflammation, cancer, and neurodegenerative disorders. In this study, 60 chalcone derivatives with fluorine (F), trifluoromethyl (CF3), trifluoromethoxy (OCF3), chlorine (Cl), and bromine (Br) in ring A and with or without hydroxy (OH) in ring B were designed, synthesized, and screened for inhibitory activity against lipopolysaccharide (LPS)-stimulated ROS production in RAW 264.7 macrophages. Structure–activity relationship study revealed the importance of a hydroxyl moiety in ring B for enhancing inhibitory activity of ROS production. Furthermore, a hydroxyl group at the ortho-position is more essential for inhibition of ROS production followed by meta- and para-positions. Among all, compound 27 that contains para-chlorine moiety in ring A and ortho-hydroxy in ring B displayed the strongest inhibitory activity (IC50 = 3.42 μM) against LPS-stimulated ROS production in RAW264.7 macrophages.
- Shrestha, Aarajana,Shrestha, Aastha,Park, Pil-Hoon,Lee, Eung-Seok
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p. 729 - 734
(2019/07/19)
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- Palladium Nanoparticles-Catalyzed Synthesis of Indanone Derivatives via Intramolecular Reductive Heck Reaction
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An efficient protocol for the straightforward, single-step synthesis of 3-aryl-1-indanones from 2′-iodochalcone via reductive Heck reaction using phosphine free, stable and reusable binaphthyl stabilized palladium nanoparticle (Pd-BNP) as a catalyst has been described. An immense array of substrate scope with electron-rich and deficient 2′-iodochalcones have been synthesized. Further derivatization of product indanones have been achieved successfully. The heterogeneous nature of the Pd-BNP has been validated by centrifugation test and mercury poisoning experiment. Pd-BNP has been successfully recycled up to 5 cycles without any significant loss in reaction yield and particle size of nanoparticles, confirmed by TEM analysis. (Figure presented.).
- Parveen, Naziya,Sekar, Govindasamy
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p. 4581 - 4595
(2019/09/03)
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- Photoinduced Gold-Catalyzed Domino C(sp) Arylation/Oxyarylation of TMS-Terminated Alkynols with Arenediazonium Salts
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A selective and convenient synthesis of tri- and tetrasubstituted α,β-unsaturated ketones, as well as 2,3-diarylbenzofurans has been developed with the aid of light and taking advantage of a cooperative gold/photoredox-catalyzed 2-fold arylation reaction of TMS-terminated alkynols. The reaction of 3-(trimethylsilyl)prop-2-yn-1-ols was competent to generate diarylated α,β-unsaturated ketones; whereas the photoredox sequence involving 2-[(trimethylsilyl)ethynyl]phenol exclusively afforded 2,3-diarylbenzofurans. The reaction of terminal alkynes proceeded in poor yields while the use of bulkier silyl groups, such as TIPS, resulted unproductive. Apparently, the C(sp) arylation reaction is the first event on the domino bis-arylative sequence. These results could be explained through the intermediation of arylgold(III) species and several single electron transfer processes.
- Alcaide, Benito,Almendros, Pedro,Busto, Eduardo,Lázaro-Milla, Carlos
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p. 2177 - 2186
(2017/02/26)
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- Copper-catalyzed intramolecular tandem reaction of (2-halogenphenyl)(3- phenyloxiran-2-yl)methanones: Synthesis of (Z)-aurones
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A convenient and efficient method for the copper-catalyzed synthesis of (Z)-aurones via intramolecular tandem reaction of (2-halogenphenyl)(3- phenyloxiran-2-yl)methanones is reported. Moreover, a plausible mechanism for the formation of (Z)-aurones is proposed. This is the first report on the synthesis of (Z)-aurones through copper-catalyzed Ullmann coupling reaction employing epoxides as substrates.
- Weng, Yiyi,Chen, Qixu,Su, Weike
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p. 4218 - 4224
(2014/05/20)
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- Buchwald-Hartwig coupling/Michael addition reactions: One-pot synthesis of 1,2-disubstituted 4-quinolones from chalcones and primary amines
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The Buchwald-Hartwig coupling/Michael addition sequence has been successfully applied to the synthesis of functionalized 1,2-disubstituted 4-quinolones using Pd(OAc)2 as a catalyst and PPh3 as a ligand. Under these conditions, the intermediate products first formed from chalcones and primary amines underwent catalytic dehydrogenation to yield the 1,2-disubstituted 4-quinolones. Copyright
- Fei, Xiang-Dong,Zhou, Zhou,Li, Wen,Zhu, Yong-Ming,Shen, Jing-Kang
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experimental part
p. 3001 - 3008
(2012/07/13)
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- One-pot production of chiral α,β-epoxy ketones from benzaldehydes and acetophenones by recyclable poly(amino acid) catalysis
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An efficient one-pot, two-step process was disclosed for production of chiral α,β-epoxy ketones from benzaldehydes and acetophenones catalyzed by imidazolium-modified poly(l-leucine). Two effective reaction systems with complementary high enantioselectivities (up to 98% ee) or satisfactory yields (up to 89%) have been developed. Importantly, the poly(amino acid) catalyst can be easily recovered and recycled for ten times without losing its catalytic efficiency in terms of both enantioselectivity and yield.
- Luo, Wanrong,Yu, Zhichao,Qiu, Wenwei,Yang, Fan,Liu, Xiaofeng,Tang, Jie
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supporting information; experimental part
p. 5289 - 5292
(2011/08/04)
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- New aromatic substituted pyrazoles as selective inhibitors of human adipocyte fatty acid-binding protein
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a-FABP is indespensible in inflammation and may serve as a new potential drug target for inflammation related diseases. We have successfully designed and synthesized a series of aromatic substituted pyrazoles as new human a-FABP inhibitors. The compounds
- Liu, Xiujie,Huang, Xiaoli,Lin, Wanhua,Wang, Dongye,Diao, Yanyan,Li, Honglin,Hui, Xiaoyan,Wang, Yu,Xu, Aimin,Wu, Donghai,Ke, Ding
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supporting information; experimental part
p. 2949 - 2952
(2011/06/24)
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- Three-step synthesis of 2,4-diaryl-5,6,7,8-tetrahydroquinoline derivatives
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(Chemical Equation Presented) Addition of cylohexanone to chalcones, obtained from the appropriate acetophenone and benzaldehyde derivatives, under solvent-free conditions gave 1,5-diketones in good yields. Treatment of 1,5-diketones with ammonium acetate in acetic acid afforded directly 2,4-diaryl-5,6,7,8-tetrahydroquinoline derivatives (7a-u) in high yields. The structures of 7a-u were elucidated by 1H NMR, 13C NMR, IR, and elemental analysis.
- Gezegen, Hayreddin,Dingil, Alparslan,Ceylan, Mustafa
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experimental part
p. 1017 - 1024
(2010/10/21)
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- Kinesin spindle protein (KSP) inhibitors. Part 1: The discovery of 3,5-diaryl-4,5-dihydropyrazoles as potent and selective inhibitors of the mitotic kinesin KSP
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Optimization of high-throughput screening (HTS) hits resulted in the discovery of 3,5-diaryl-4,5-dihydropyrazoles as potent and selective inhibitors of KSP. Dihydropyrazole 15 is a potent, cell-active KSP inhibitor that induces apoptosis and generates aberrant mitotic spindles in human ovarian carcinoma cells at low nanomolar concentrations. X-ray crystallographic evidence is presented which demonstrates that these inhibitors bind in an allosteric pocket of KSP distant from the nucleotide and microtubule binding sites.
- Cox, Christopher D.,Breslin, Michael J.,Mariano, Brenda J.,Coleman, Paul J.,Buser, Carolyn A.,Walsh, Eileen S.,Hamilton, Kelly,Huber, Hans E.,Kohl, Nancy E.,Torrent, Maricel,Yan, Youwei,Kuo, Laurence C.,Hartman, George D.
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p. 2041 - 2045
(2007/10/03)
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