- Synthesis of Quinolines via Iron-Catalyzed Redox Condensation of Alcohols with 2-Nitrobenzyl Methyl Ether/2-Nitrobenzyl Alcohols
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An iron-catalyzed redox condensation of 2-nitrobenzyl alcohols, formic acid, and alcohols has been developed, which affords substituted quinolines with carbon dioxide and water as the only side products. With the use of formic acid as a redox moderator to fill the electron gap of the global redox condensation process, the reaction goes smoothly with a smaller amount of alcohol in comparison to previous reports (i.e. 1.2 equiv versus 3.3-4 equiv). The reaction goes equally well when 2-nitrobenzyl methyl ether was used instead of 2-nitrobenzyl alcohol under otherwise identical conditions, shedding a new light on the study of this quinoline synthetic method.
- Wang, Qi,Wang, Meirong,Li, Hui-Jing,Zhu, Shuai,Liu, Ying,Wu, Yan-Chao
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- NiH-Catalyzed Hydroamination/Cyclization Cascade: Rapid Access to Quinolines
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Despite the significant success of metal-H-catalyzed hydroamination methodologies, considerable limitations still exist in the selective hydroamination of alkynes, especially for terminal alkynes. Herein, we develop a highly efficient NiH catalytic system that activates readily available alkynes for a cascade hydroamination/cyclization reaction with anthranils. This mild, operationally simple protocol is amenable to a wide array of alkynes including terminal and internal, aryl and alkyl, electron-deficient and electron-rich ones, delivering structurally diverse quinolines in useful to excellent yields (>80 examples, up to 93% yield). The utility of this procedure is exhibited in the late-stage functionalization of several natural products and in the concise synthesis of an antitumor molecule graveolinine and a triplex DNA intercalator. Preliminary mechanistic experiments suggest an alkenylnickel-mediated alkyne hydroamination and an intramolecular cyclization/aromatization of putative enamine intermediates.
- Chen, Qian,Gao, Yang,Hu, Xiao-Qiang,Huo, Yanping,Li, Xianwei,Yang, Simin
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p. 7772 - 7779
(2021/06/30)
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- Quinoline derivative as well as preparation method and application thereof
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The invention belongs to the technical field of chemical drug synthesis, and particularly relates to a quinoline derivative as well as a preparation method and application thereof. In a reaction system, firstly, a metal catalyst, a ligand and a silicon hydrogen reagent interact to generate metal hydride, the metal hydride and an alkyne compound are subjected to addition, the metal hydride and an anthranil compound are subjected to an electrophilic amination reaction, and then the polysubstituted quinoline derivative is obtained through intramolecular cyclization. According to the invention, the starting raw materials such as the alkyne and the anthranil compound of the reaction are cheap and easily available, a variety of different polysubstituted quinoline derivatives can be constructed by using the one-step method, and can be rapidly converted into other compounds through the oxidation, the reduction, the coupling and other approaches of the target molecule so as to provide the good application prospect in the fields of drug development and material preparation; and the method is mild in condition, green, efficient, simple to operate and very suitable for large-scale industrial production.
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Paragraph 0161-0168
(2021/07/17)
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- Mild and efficient copper-catalyzed oxidative cyclization of oximes with 2-aminobenzyl alcohols at room temperature: synthesis of polysubstituted quinolines
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A simple and efficient ligand-free Cu-catalyzed protocol for the synthesis of polysubstituted quinolinesviaoxidative cyclization of oxime acetates with 2-aminobenzyl alcohols at room temperature has been developed. The presented approach provides a new synthetic pathway leading to polysubstituted quinolines with good functional group tolerance under mild conditions. Moreover, this transformation can be applied for the preparation of quinolines on a gram scale. Oxime acetates serve as the internal oxidants in the reactions, thus making this method very attractive.
- Liu, Yan-Yun,Wei, Yang,Huang, Zhi-Hui,Liu, Yilin
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supporting information
p. 659 - 666
(2021/02/06)
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- Molybdenum-Catalyzed Sustainable Friedl?nder Synthesis of Quinolines
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Polysubstituted quinolines have been efficiently synthesized from nitroarenes and glycols, as reducing agents, under dioxomolybdenum(VI)-catalysis. Interestingly, the waste reduction byproduct is incorporated into the final heterocycle. This method repres
- Rubio-Presa, Rubén,Suárez-Pantiga, Samuel,Pedrosa, María R.,Sanz, Roberto
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supporting information
p. 2216 - 2220
(2018/06/14)
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- Synthesis of Polysubstituted Quinolines from α-2-Aminoaryl Alcohols Via Nickel-Catalyzed Dehydrogenative Coupling
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This study reports a nickel-catalyzed sustainable synthesis of polysubstituted quinolines from α-2-aminoaryl alcohols by a sequential dehydrogenation and condensation process that offers the advantages of a low catalyst loading and wide substrate scope. In contrast to earlier reported methods, this strategy allows the use of both primary as well as secondary α-2-aminoaryl alcohols in combination with either ketones or secondary alcohols for desired product formation. Using this methodology, 30 substituted quinoline derivatives were synthesized with up to 93% isolated yields.
- Das, Sanju,Maiti, Debabrata,De Sarkar, Suman
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p. 2309 - 2316
(2018/02/23)
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- Iridium-catalyzed synthesis of quinolines from 2-aminobenzyl alcohols with secondary alcohols
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The quinoline derivatives were synthesized from 2-aminobenzyl alcohols and secondary alcohols by the direct one-step synthesis using the iridium complexes as catalyst. This efficient and easy method is suitable for all kinds of substituted quinolines.
- Yu,Yao,Hu,Wang
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p. 376 - 379
(2016/04/20)
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- Convenient synthesis of quinolines from α-2-nitroaryl alcohols and alcohols via a ruthenium-catalyzed hydrogen transfer strategy
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A new and straightforward method for convenient synthesis of quinolines via a ruthenium-catalyzed hydrogen-transfer strategy has been demonstrated. By employing a commercially available ruthenium catalyst system, different α-2-nitroaryl alcohols were efficiently converted in combination with a variety of alcohols into various substituted products in reasonable to good yields upon isolation. The synthetic protocol is operationally simple with a broad substrate scope, and there is no need for the use of specialized reducing agents, making it a practical approach for versatile preparation of various quinoline derivatives.
- Xie, Feng,Zhang, Min,Chen, Mengmeng,Lv, Wan,Jiang, Huanfeng
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p. 349 - 353
(2015/03/05)
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- Construction of a quinoline ring via a 3-component reaction in water: Crystal structure analysis and H-bonding patterns of a 2-aryl quinoline
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Montmorillonite K-10 mediated green and one-pot synthesis of 2-substituted quinolines has been accomplished via a 3-component reaction of aniline, aldehydes and ethyl 3,3-diethoxypropionate in the presence of air oxygen in water. The crystal structure analysis and H-bonding patterns of one compound prepared are presented. The Royal Society of Chemistry 2012.
- Reddy, T. Ram,Reddy, L. Srinivasula,Reddy, G. Rajeshwar,Yarbagi, Kaviraj,Lingappa,Rambabu,Krishna, G. Rama,Reddy, C. Malla,Kumar, K. Shiva,Pal, Manojit
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supporting information; experimental part
p. 1870 - 1872
(2012/07/17)
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- A FACILE AND ALTERNATIVE SYNTHESIS OF QUINOLINE NUCLEUS USING THERMAL CYCLIZATION OF 2-AZAHEXATRIENE SYSTEM GENERATED FROM 2-ALKENYL ACYLANILINE WITH POCl3
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The thermal cyclization of 2-alkenyl acylanilines with POCl3 in toluene or xylene gave quinoline derivatives in good yield via 2-azahexatriene system in situ.
- Hibino, Satoshi,Sugino, Eiichi
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p. 1883 - 1889
(2007/10/02)
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