- Synthesis derivatives of 2-amino-4-quinolones from 1,2,3,4- tetrahydroquinoline-8-carboxylic acids
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A simple and efficient method is developed. Novel 2-amino-4-quinolone derivatives are synthesized. The products that have several functional groups for possible future modifications are described.
- Listunov, Dimitriy,Popov, Kirill,Tkachuk, Tetyana,Volovenko, Yulian
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- Method for preparing 8-quinoline carboxylic acid and derivatives of 8-quinoline carboxylic acid
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The invention discloses a method for preparing 8-quinoline carboxylic acid and derivatives thereof, which comprises the following steps: by using a compound I as a raw material, reacting with an oxidant at the temperature of 50-150 DEG C under normal pressure in a solvent under the action of a Cu-Co-X ternary composite catalyst to obtain a compound II; according to the method, the efficient Cu-Co-X ternary composite catalyst is adopted, the reaction is carried out at the temperature of 50-150 DEG C under normal pressure, the reaction condition is mild, the oxidation yield is remarkably increased, near-zero emission of three wastes is realized, the pollution problem is effectively solved, and the production cost is greatly reduced.
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Paragraph 0018-0019
(2021/01/15)
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- Redox couple involving NOx in aerobic Pd-catalyzed oxidation of sp3-C-H bonds: Direct Evidence for Pd-NO3-/NO2- interactions involved in oxidation and reductive elimination
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NaNO3 is used in oxidative Pd-catalyzed processes as a complementary co-catalyst to common oxidants, e.g., CuII salts, in C-H bond activation and Wacker oxidation processes. NaNO3 and NaNO2 (with air or O2
- Wenzel, Margot N.,Owens, Philippa K.,Bray, Joshua T.W.,Lynam, Jason M.,Aguiar, Pedro M.,Reed, Christopher,Lee, James D.,Hamilton, Jacqueline F.,Whitwood, Adrian C.,Fairlamb, Ian J.S.
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p. 1177 - 1190
(2017/05/16)
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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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- Insertion of an Alkene into an ester: Intramolecular oxyacylation reaction of alkenes through acyl C-O bond activation
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Atom economy and esters: compatible now! The first catalytic insertion of a C-C bond into an acyl C-O bond was achieved using rhodium catalysts (see scheme). The products are β-alkoxy ketones with a fully substituted carbon center. Quinoline chelating groups were employed to stabilize the Rh-alkoxide intermediate.
- Hoang, Giang T.,Reddy, Venkata Jaganmohan,Nguyen, Huy H. K.,Douglas, Christopher J.
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supporting information; experimental part
p. 1882 - 1884
(2011/04/16)
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- Remarkable effect of nitrogen dioxide for N-hydroxyphthalimide-catalyzed aerobic oxidation of methylquinolines
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Aerobic oxidation of methylquinolines was successfully achieved by the use of N-hydroxyphthalimide/Co(OAc)2/Mn(OAc)2 as catalyst in the presence of a small amount of nitrogen dioxide as an initiator.
- Sakaguchi, Satoshi,Shibamoto, Akihiro,Ishii, Yasutaka
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p. 180 - 181
(2007/10/03)
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- Biocatalytic oxidation of 2-methylquinoxaline to 2-quinoxalinecarboxylic acid
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A microbial process using the fungus Absidia repens ATCC 14849 is described for the oxidation of 2-methylquinoxaline to 2-quinoxalinecarboxylic acid. A campaign consisting of three 14000-L runs produced 20.5 kg of the acid with a 28% overall yield. The bioconversion gave a lower yield compared with a three step chemical synthesis (35%), but was carried out in one pot, and avoided safety issues with a di-N-oxide intermediate. Although successfully scaled to produce kilograms of 2-quinoxalinecarboxylic acid for synthesis of a drug candidate, the A. repens bioconversion is unsuitable for further scale-up due to low product concentration (~1 g/L). A second microbial process using Pseudomonas putida ATCC 33015 is also described for the oxidation of 2-methylquinoxaline. The P. putida bioconversion gave an 86% in situ yield at 8-L scale and yielded a product concentration approximately 10-fold greater than that of the A. repens bioconversion.
- Wong, John W.,Watson Jr., Harry A.,Bouressa, James F.,Burns, Michael P.,Cawley, James J.,Doro, Albert E.,Guzek, Donald B.,Hintz, Michael A.,McCormick, Ellen L.,Scully, Douglas A.,Siderewicz, Joseph M.,Taylor, William J.,Truesdell, Susan J.,Wax, Richard G.
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p. 477 - 481
(2013/09/06)
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- ALKALOIDS OF Nitraria komarovii. IV. TOTAL SYNTHESIS OF KOMAROVINE AND KOMAROVIDINE
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Two alkaloids of a new type - komarovine and komarovidine - have been isolated from the epigeal part of the Nitraria komarovii.Their structures - 3-(quinolin-8'-yl)-β-carboline and 3-(quinolin-8'-yl)-5,6-dihydro-β-carboline, respectively - have been established by synthesis.
- Tulyaganov, T. S.,Ibragimov, A. A.,Yunusov, S. Yu.
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p. 149 - 152
(2007/10/02)
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