- Scalable Photoelectrochemical Dehydrogenative Cross-Coupling of Heteroarenes with Aliphatic C?H Bonds
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Heteroarenes are structural motifs found in many bioactive compounds and functional materials. Dehydrogenative cross-coupling of heteroarenes with aliphatic C?H bonds provides straightforward access to functionalized heteroarenes from readily available materials. Established methods employ stoichiometric chemical oxidants under conditions of heating or light irradiation. By merging electrochemistry and photochemistry, we have achieved efficient photoelectrochemical dehydrogenative cross-coupling of heteroarenes and C(sp3)?H donors through H2 evolution, without the addition of metal catalysts or chemical oxidants. Mechanistically, the C(sp3)?H donor is converted to a nucleophilic carbon radical through H-atom transfer with chlorine atom, which is produced by light irradiation of anodically generated Cl2 from Cl?. The carbon radical then undergoes radical substitution to the heteroarene to afford alkylated heteroarene products.
- Chen, Peng-Yu,Xu, Hai-Chao,Xu, Pin
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supporting information
p. 14275 - 14280
(2020/07/13)
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- An efficient and direct synthesis of substituted 2-phenylquinoline-4-carboxamides from 3-substituted-3-hydroxyindolin-2-ones
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A simple and direct synthesis of substituted 2-phenylquinoline-4-carboxamides from 3-substituted-3-hydroxyindolines in presence of ammonium acetate is described. The developed protocol also allows synthesis of the carboxamide moeity directly from isatin a
- Tiwari, Keshri Nath,Choubey, Rinku,Shukla, Saumya,Gautam, Parul
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p. 165 - 173
(2018/07/05)
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- Cu-Catalyzed Coupling of O-Acyl Oximes with Isatins: Domino Rearrangement Strategy for Direct Access to Quinoline-4-Carboxamides by C–N Bond Cleavage
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A mild domino rearrangement strategy for the direct access to substituted quinoline-4-carboxamides has been developed. This copper-catalyzed coupling reaction of O-acyl oximes with isatins in the presence of molecular oxygen as the sole oxidizing agent proceeds through a ring expansion of the isatins through cleavage of the two C–N bonds.
- Ramaraju, Andhavaram,Chouhan, Neeraj Kumar,Ravi, Owk,Sridhar, Balasubramanian,Bathula, Surendar Reddy
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p. 2963 - 2971
(2018/06/27)
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- I2-Triggered Reductive Generation of N-Centered Iminyl Radicals: An Isatin-to-Quinoline Strategy for the Introduction of Primary Amides
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An efficient and alternative isatin-to-quinoline strategy illustrates the metal-like behavior of molecular iodine in the N?O reduction of ketoxime acetates. This process involves N?O/C?N bond cleavages and C?C/C?N bond formation to furnish pharmacologically significant quinoline-4-carboxamide derivatives. In this process, metal catalysts and extra oxidants are unnecessary. Mechanistic studies confirm the crucial role of molecular iodine in the iminyl radical generation process, in that molecular iodine can catalyze single-electron reduction coupling reactions in a manner similar to transition metals. (Figure presented.).
- Gao, Qinghe,Liu, Zhaomin,Wang, Yakun,Wu, Xia,Zhang, Jixia,Wu, Anxin
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supporting information
p. 1364 - 1369
(2018/02/12)
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- Synthetic method of quinoline-4-formamides compound
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The invention discloses a synthetic method of a quinoline-4-formamides compound, and belongs to the technical field of organic synthesis. The the invention is characterized in that the synthetic method of the quinoline-4-formamides compound comprises the following steps: dissolving an oxime ester acetate compound and isatin or a derivative of the oxime ester acetate compound and the isatin in a solvent; then adding a catalyst and alkali to carry out reaction at 100 to 130 DEG C in a sealing tube to prepare the quinoline-4-formamides compound. A synthetic process of the synthetic method disclosed by the invention is simple and high-efficient; through one-pot series connection reaction, the quinoline-4-formamides compound is directly prepared in one step, so that resource waste and environment pollution caused by the use of a plurality of reagents in multi-step reaction, purification treatment on intermediates obtained in all reaction steps and the like are avoided, raw materials are cheap and easy to get or the raw materials are easy to prepare; reaction conditions are mild, and a substrate has a wide application range.
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Paragraph 0015; 0016; 0017; 0018; 0019; 0020-0037
(2018/01/11)
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- QUINOLINES DERIVATIVES AS NOVEL ANTICANCER AGENTS
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The invention provides quinoline derivatives, their manufacture, pharmaceutical compositions containing them, and their use as medicaments. The active compounds of the present invention are useful for the treatment of proliferative neoplastic and nonneoplastic diseases.
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Page/Page column 115; 116
(2014/10/03)
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