- Electrochemical and spectroscopic behaviors of a novel ruthenium(II) Complex with a Six-Membered Chelate Structure
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A novel polypyridyl ruthenium(II) complex with a six-membered chelate ring ([Ru(dmb)2(8pyq)]2+) was designed and synthesized. The oxidation potential was shifted to the negative potential direction, and relatively intense metal-to-ligand charge transfer absorption in the longer-wavelength region was observed for [Ru(dmb)2(8pyq)]2+ compared with the reference complexes without any six-membered chelate rings. The electrochemical and spectroscopic properties of [Ru(dmb)2(8pyq)]2+ were discussed in terms of the chelate structure and coordination geometry with utilization of theoretical calculations.
- Ito, Akitaka,Matsui, Yushi
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- Kinetic Resolution of Axially Chiral 5- or 8-Substituted Quinolines via Asymmetric Transfer Hydrogenation
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An efficient kinetic resolution of axially chiral 5- or 8-substituted quinoline derivatives was developed through asymmetric transfer hydrogenation of heteroaromatic moiety, simultaneously obtaining two kinds of axially chiral skeletons with up to 209 of selectivity factor. This represents the first successful application of asymmetric transfer hydrogenation of heteroaromatics in kinetic resolution of axially chiral biaryls.
- Wang, Jie,Chen, Mu-Wang,Ji, Yue,Hu, Shu-Bo,Zhou, Yong-Gui
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- Optical p Ka Control in a Bifunctional Iridium Complex
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There are few ways to switch a catalyst's reactivity on or off, or change its selectivity, with external radiation; many of these involve photochemical activation of a catalyst. In the case of homogeneous late-transition-metal catalysts, the metal complex itself is frequently the chromophore involved in such reactivity switching. We show here a base-pendant ligand-metal bifunctional scaffold wherein a photobase, a compound that becomes more basic in the excited state (pKa a?), is used to switch the proton acceptor ability on an active site of the complex. The system differs from those with metal-centered chromophores, because the photobase operates independently of the metal. While excellent progress has been made in photoacid chemistry, neither a photoacid nor a photobase has been designed into the structure of a transition-metal catalyst where the metal is not part of the chromophore. We find that quinoline is an efficient photobase that preserves its unique properties in the close proximity of an iridium center: the efficacy of the photobase (9.3 a? a control in a transition-metal complex.
- Demianets, Ivan,Hunt, Jonathan R.,Dawlaty, Jahan M.,Williams, Travis J.
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- Synthesis of functionalized porphyrins as oxygen ligand receptors
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Oxophilic synthetic receptors were designed and synthesized using a porphyrin scaffold, with the aim of constructing a preorganized complementary binding site for phenols and carbohydrates. We pursued three strategies for phenol recognition: (1) Lewis aci
- Wada, Kenji,Mizutani, Tadashi,Kitagawa, Susumu
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- Pd-Catalyzed C-H Halogenation of Indolines and Tetrahydroquinolines with Removable Directing Group
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Pd-catalyzed directing-group-assisted regioselective halogenations to C7 of indolines and C8 of tetrahydroquinolines were achieved in good to excellent yields. The practicality and utility of the developed method have been illustrated by various functiona
- Ahmad, Ashfaq,Dutta, Himangsu Sekhar,Kumar, Mohit,Khan, Afsar Ali,Raziullah,Koley, Dipankar
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- Direct bromodeboronation of arylboronic acids with CuBr2 in water
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An efficient and practical method has been developed for the preparation of aryl bromides via the direct bromodeboronation of arylboronic acids with CuBr2 in water. This strategy provides several advantages, such as being ligand-free, base-free, high yielding, and functional group tolerant.
- Tang, Yan-Ling,Xia, Xian-Song,Gao, Jin-Chun,Li, Min-Xin,Mao, Ze-Wei
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supporting information
(2021/01/05)
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- Structure-activity relationships, biological evaluation and structural studies of novel pyrrolonaphthoxazepines as antitumor agents
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Microtubule-targeting agents (MTAs) are a class of clinically successful anti-cancer drugs. The emergence of multidrug resistance to MTAs imposes the need for developing new MTAs endowed with diverse mechanistic properties. Benzoxazepines were recently identified as a novel class of MTAs. These anticancer agents were thoroughly characterized for their antitumor activity, although, their exact mechanism of action remained elusive. Combining chemical, biochemical, cellular, bioinformatics and structural efforts we developed improved pyrrolonaphthoxazepines antitumor agents and their mode of action at the molecular level was elucidated. Compound 6j, one of the most potent analogues, was confirmed by X-ray as a colchicine-site MTA. A comprehensive structural investigation was performed for a complete elucidation of the structure-activity relationships. Selected pyrrolonaphthoxazepines were evaluated for their effects on cell cycle, apoptosis and differentiation in a variety of cancer cells, including multidrug resistant cell lines. Our results define compound 6j as a potentially useful optimized hit for the development of effective compounds for treating drug-resistant tumors.
- Brindisi, Margherita,Ulivieri, Cristina,Alfano, Gloria,Gemma, Sandra,de Asís Balaguer, Francisco,Khan, Tuhina,Grillo, Alessandro,Chemi, Giulia,Menchon, Grégory,Prota, Andrea E.,Olieric, Natacha,Lucena-Agell, Daniel,Barasoain, Isabel,Diaz, J. Fernando,Nebbioso, Angela,Conte, Mariarosaria,Lopresti, Ludovica,Magnano, Stefania,Amet, Rebecca,Kinsella, Paula,Zisterer, Daniela M.,Ibrahim, Ola,O'Sullivan, Jeff,Morbidelli, Lucia,Spaccapelo, Roberta,Baldari, Cosima,Butini, Stefania,Novellino, Ettore,Campiani, Giuseppe,Altucci, Lucia,Steinmetz, Michel O.,Brogi, Simone
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p. 290 - 320
(2018/11/24)
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- Rh(III)-Catalyzed C(8)-H Activation of Quinoline N-Oxides: Regioselective C-Br and C-N Bond Formation
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A highly efficient and regioselective Rh(III)-catalyzed protocol for C8-bromination and amidation of quinoline N-oxide was developed. The transformation was found to be successful up to gram scale with excellent functional group tolerance and wide substrate scope. The mechanistic study revealed five-membered rhodacycle with quinoline N-oxide as a key intermediate for regioselective C8-functionalization. In addition, NFSI (N-fluorobis(phenylsulfonyl)-imide) was explored as an amidating reagent for C8-amidation of quinoline N-oxide for the first time.
- Dhiman, Ankit Kumar,Gupta, Shiv Shankar,Sharma, Ritika,Kumar, Rakesh,Sharma, Upendra
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p. 12871 - 12880
(2019/11/02)
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- Induction of Axial Chirality in 8-Arylquinolines through Halogenation Reactions Using Bifunctional Organocatalysts
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The enantioselective syntheses of axially chiral heterobiaryls were accomplished through the aromatic electrophilic halogenation of 3-(quinolin-8-yl)phenols with bifunctional organocatalysts that control the molecular conformations during successive halogenations. Axially chiral quinoline derivatives, which have rarely been synthesized in an enantioselective catalytic manner, were afforded in moderate-to-good enantioselectivities through bromination, and an analogous protocol also enabled enantioselective iodination. In addition, this catalytic reaction, which allows enantioselective control through the use of mono-ortho-substituted substrates, allowed the asymmetric synthesis of 8-arylquinoline derivatives bearing two different halogen groups in high enantioselectivities.
- Miyaji, Ryota,Asano, Keisuke,Matsubara, Seijiro
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supporting information
p. 9996 - 10000
(2017/08/01)
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- Development and Mechanistic Study of Quinoline-Directed Acyl C-O Bond Activation and Alkene Oxyacylation Reactions
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The intramolecular addition of both an alkoxy and acyl substituent across an alkene, oxyacylation of alkenes, using rhodium catalyzed C-O bond activation of an 8-quinolinyl ester is described. Our unsuccessful attempts at intramolecular carboacylation of ketones via C-C bond activation ultimately informed our choice to pursue and develop the intramolecular oxyacylation of alkenes via quinoline-directed C-O bond activation. We provide a full account of our catalyst discovery, substrate scope, and mechanistic experiments for quinoline-directed alkene oxyacylation.
- Hoang, Giang T.,Walsh, Dylan J.,McGarry, Kathryn A.,Anderson, Constance B.,Douglas, Christopher J.
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p. 2972 - 2983
(2017/03/23)
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- Method for catalyzing nitrogen heterocyclic ring compound for oxidative dehydrogenation with hydrotalcite-like material
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The invention relates to a method for catalyzing a nitrogen heterocyclic ring compound for oxidative dehydrogenation with a hydrotalcite-like material, and belongs to the application aspect of a hydrotalcite-like component. The hydrotalcite-like component can be expressed as: A-MxM-LDHs (A=OH or CO3; M=Ni, Co, Cu, Mg or Zn; M=Fe, Mn, Al; M/M=(2 to 4)). Under existence of the catalyst and without adding any additives, oxidative dehydrogenation reaction is performed on the heterocyclic ring compound under a mild condition to prepare a corresponding aromatic compound. According to the method provided by the invention, the hydrotalcite-like material is based on non-noble metal, can be synthesized largely, and can be recycled; the method has the advantages of being high in catalytic reaction efficiency, mild in reaction condition, low in cost, easy to industrialize and the like.
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Paragraph 0048; 0049; 0050; 0051; 0053
(2017/10/27)
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- Quinoline synthesis by improved Skraup-Doebner-Von Miller reactions utilizing acrolein diethyl acetal
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A robust synthetic method has been developed as an improvement to the venerable Skraup-Doebner-Von Miller reaction providing access to various quinoline products. The straightforward procedure utilizes acrolein diethyl acetal as a three-carbon annulation partner with aniline substrates in a monophasic, organic solvent-free reaction medium. Differentially substituted aniline precursors were found to be compatible with the reaction conditions and the corresponding quinoline products are isolated in moderate to good yields.
- Ramann, Ginelle A.,Cowen, Bryan J.
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supporting information
p. 6436 - 6439
(2015/11/16)
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- Highly efficient dye-sensitized solar cells based on panchromatic ruthenium sensitizers with quinolinylbipyridine anchors
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Panchromatic RuII sensitizers TF-30-TF-33 bearing a new class of 6-quinolin-8-yl-2,2′-bipyridine anchor were synthesized and tested under AM1.5 G simulated solar irradiation. Their increased π conjugation relative to that of the traditional 2,2
- Chou, Chun-Cheng,Hu, Fa-Chun,Yeh, Hsiu-Hsuan,Wu, Hsin-Pei,Chi, Yun,Clifford, John N.,Palomares, Emilio,Liu, Shih-Hung,Chou, Pi-Tai,Lee, Gene-Hsiang
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supporting information
p. 178 - 183
(2014/01/17)
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- Alkyl(quinolin-8-yl)phosphine oxides as hemilabile preligands for palladium-catalyzed reactions
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Preligands of quinolyl-substituted secondary phosphine oxides (SPOs, 2a-d) were prepared and characterized. The unique palladium complex 3, having a distorted-square-pyramidal structure, was obtained from the reaction of 2 equiv of 2c with Pd(COD)Cl2 or [Pd(μ2-Cl)(η3- allyl)]2. In the crystal structure of 3, an apical chloride ligand and a supramolecular tetradentate ligand composed of a deprotonated 2c' and a neutral 2c' were resolved (2c': PA form of 2c). Intriguingly, the gas-phase optimized geometry of 3 converged to a distorted-square-planar structure, which was predicted by density functional calculations. The solid-state distorted-square-pyramidal structure of 3 can only be explained with the consideration of environmental effects (i.e., the electrostatic interactions between the surrounding molecules). As also evidenced by 31P NMR experiments performed in different deuterated solvents, the crystal structure of 3 is retained in solution. In the crystal structure of 3, a long Pd-Cl bond was analyzed by energy decomposition analysis, showing that the bond is dominated by electrostatic character. Furthermore, application of these SPOs using the Heck reaction shows good reactivity toward common aryl bromides. The hemilabile preligand 2c also tautomerizes to the competent ligand 2c' for palladium-catalyzed three-component reactions.
- Chang, Yu-Chang,Chang, Wei-Chan,Hu, Chan-Yu,Hong, Fung-E
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p. 3523 - 3534
(2014/08/05)
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- One-pot synthesis of N-aryl propargylamine from aromatic boronic acid, aqueous ammonia, and propargyl bromide under microwave-assisted conditions
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A facile, one-pot synthesis of N-aryl propargylamine from aromatic boronic acid, aqueous ammonia, and propargyl bromide has been achieved under microwave-assisted conditions. The reactions can be smoothly completed within a total 10 min through a two-step procedure, including copper-catalyzed coupling of aromatic boronic acids with aqueous ammonia and following propargylation by propargyl bromide.
- Jiang, Yu-Bo,Zhang, Wen-Sheng,Cheng, Hui-Ling,Liu, Yu-Qi,Yang, Rui
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p. 779 - 782
(2014/06/09)
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- BROMINATION OF QUINOLINE DERIVATIVES WITH N-BROMOSUCCINIMIDE. ISOMERIC COMPOSITION OF THE BROMINATION PRODUCTS BY PMR AND GLC
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The bromination of quinoline and substituted quinolines with N-bromosuccinimide in concentrated H2SO4 takes place exclusively in the homocyclic part.Bromo-substituted quinolines can be obtained by this method.The bromination products were identified by PMR spectroscopy.The differences among the mono-, di-, and trisubstituted (in the benzene ring) compounds were established on the basis of the type of spectrum of the protons of the homocyclic part of the molecule.The compositions of the reaction mixtures were studied by GLC.
- Tochilkin, A. I.,Kovel'man, I. R.,Prokof'ev, E. P.,Gracheva, I. N.,Levinskii, M. V.
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p. 892 - 897
(2007/10/02)
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