- Modular Access to Spiro-dihydroquinolines via Scandium-Catalyzed Dearomative Annulation of Quinolines with Alkynes
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The catalytic enantioselective construction of three-dimensional molecular architectures from planar aromatics such as quinolines is of great interest and importance from the viewpoint of both organic synthesis and drug discovery, but there still exist many challenges. Here, we report the scandium-catalyzed asymmetric dearomative spiro-annulation of quinolines with alkynes. This protocol offers an efficient and selective route for the synthesis of spiro-dihydroquinoline derivatives containing a quaternary carbon stereocenter with an unprotected N-H group from readily accessible quinolines and diverse alkynes, featuring high yields, high enantioselectivity, 100% atom-efficiency, and broad substrate scope. Experimental and density functional theory studies revealed that the reaction proceeded through the C-H activation of the 2-aryl substituent in a quinoline substrate by a scandium alkyl (or amido) species followed by alkyne insertion into the Sc-aryl bond and the subsequent dearomative 1,2-addition of the resulting scandium alkenyl species to the C=N unit in the quinoline moiety. This work opens a new avenue for the dearomatization of quinolines, leading to efficient and selective construction of spiro molecular architectures that were previously difficult to access by other means.
- Lou, Shao-Jie,Luo, Gen,Yamaguchi, Shigeru,An, Kun,Nishiura, Masayoshi,Hou, Zhaomin
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supporting information
p. 20462 - 20471
(2021/12/03)
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- Visible-Light-Mediated Oxidative Cyclization of 2-Aminobenzyl Alcohols and Secondary Alcohols Enabled by an Organic Photocatalyst
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This paper describes a visible-light-mediated oxidative cyclization of 2-aminobenzyl alcohols and secondary alcohols to produce quinolines at room temperature. This photocatalytic method employed anthraquinone as an organic small-molecule catalyst and DMSO as an oxidant. According to this present procedure, a series of quinolines were prepared in satisfactory yields.
- Xu, Jing-Xiu,Pan, Nan-Lian,Chen, Jia-Xi,Zhao, Jin-Wu
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p. 10747 - 10754
(2021/08/16)
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- Iron Single Atom Catalyzed Quinoline Synthesis
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The production of high-value chemicals by single-atom catalysis is an attractive proposition for industry owing to its remarkable selectivity. Successful demonstrations to date are mostly based on gas-phase reactions, and reports on liquid-phase catalysis are relatively sparse owing to the insufficient activation of reactants by single-atom catalysts (SACs), as well as, their instability in solution. Here, mechanically strong, hierarchically porous carbon plates are developed for the immobilization of SACs to enhance catalytic activity and stability. The carbon-based SACs exhibit excellent activity and selectivity (≈68%) for the synthesis of substituted quinolines by a three-component oxidative cyclization, affording a wide assortment of quinolines (23 examples) from anilines and acetophenones feedstock in an efficient, atom-economical manner. Particularly, a Cavosonstat derivative can be synthesized through a one-step, Fe1-catalyzed cyclization instead of traditional Suzuki coupling. The strategy is also applicable to the deuteration of quinolines at the fourth position, which is challenging by conventional methods. The synthetic utility of the carbon-based SAC, together with its reusability and scalability, renders it promising for industrial scale catalysis.
- Chen, Zhongxin,Song, Jingting,Peng, Xinwen,Xi, Shibo,Liu, Jia,Zhou, Wenhui,Li, Runlai,Ge, Rile,Liu, Cuibo,Xu, Haisen,Zhao, Xiaoxu,Li, Haohan,Zhou, Xin,Wang, Lu,Li, Xing,Zhong, Linxin,Rykov, Alexandre I.,Wang, Junhu,Koh, Ming Joo,Loh, Kian Ping
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- Ruthenium-catalyzed acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones to quinolines in the presence of carbonate salt
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A ruthenium complex bearing a functional 2,2′-bibenzimidazole ligand [(p-cymene)Ru(BiBzImH2)Cl][Cl] was designed, synthesized and found to be a general and highly efficient catalyst for the synthesis of quinolines via acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones in the presence of carbonate salt. It was confirmed that NH units in the ligand are crucial for catalytic activity. The application of this catalytic system for the scale-gram synthesis of biologically active molecular was also undertaken. Notably, this research exhibits new potential of metal–ligand bifuctional catalysts for acceptorless dehydrogenative reactions.
- Xu, Xiangchao,Ai, Yao,Wang, Rongzhou,Liu, Liping,Yang, Jiazhi,Li, Feng
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p. 340 - 349
(2021/02/27)
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- A cobalt-catalyzed method for synthesizing quinoline and quinazoline compounds
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The present invention discloses a cobalt-catalyzed synthesis of quinoline and quinazoline compounds, by a benzene compound with amino and hydroxyl groups or benzonitrile compounds as raw materials, in the presence of a catalyst and a base by a receptor-fr
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Paragraph 0011; 0051
(2022/01/10)
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- Efficient access to quinolines and quinazolines by ruthenium complexes catalyzed acceptorless dehydrogenative coupling of 2-aminoarylmethanols with ketones and nitriles
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Treatment of N,N,O-tridentate pyrazolyl-pyridinyl-alcohol ligands, 2-(CR1R2OH)-6-[3,5-(R3)2C3HN2]C5H3N (R1 = R2 = Me, R3 = H (L1H); R1 = Me, R2 = Ph, R3 = H (L2H); R1 = R2 = Ph, R3 = H (L3H); R1 = R2 = R3 = Me (L4H)) with RuCl3?xH2O in refluxing EtOH afforded the corresponding Ru(III) complexes L2RuCl (1a-1d), which were well characterized by IR, HR-MS and X-ray single crystal structural determination. These Ru complexes showed similarly high catalytic performance for both dehydrogenative couplings of 2-aminoarylmethanols with ketones and nitriles, giving the quinolines and quinazolines in good to excellent yields. This protocol provides an atom-economical and sustainable route to access various structurally important quinoline and quinazoline derivatives by using phosphine-free ligand based Ru catalysts.
- Feng, Qi,Han, Zhangang,Hao, Zhiqiang,Huo, Shuaicong,Kong, Siqi,Lin, Jin,Lu, Guo-Liang,Zeng, Guang
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- Rhodium-Catalyzed Dehydrogenative Annulation of N-Arylmethanimines with Vinylene Carbonate for Synthesizing Quinolines
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Here we report a novel Rh-catalyzed C-H/C-H alkenylation of N-arylmethanimines with vinylene carbonate acting as a vinylene unit. Forty examples of C3,C4-nonsubstituted quinolines were achieved from commercially available starting materials. This identified process features an exceedingly simple system, a lower loading of catalyst, and the capacity for postfunctionalization with bioactive molecules.
- Hu, Yan,Nan, Jiang,Yin, Jiacheng,Huang, Guanjie,Ren, Xin,Ma, Yangmin
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p. 8527 - 8532
(2021/11/13)
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- Enantioselective Synthesis of Tetrahydroquinolines via One-Pot Cascade Biomimetic Reduction?
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A novel and efficient protocol for the synthesis of chiral tetrahydroquinoline derivatives with excellent enantioselectivities and high yields has been developed through one-pot cascade biomimetic reduction. The detailed reaction pathway includes the acid-catalyzed and ruthenium-catalyzed formation of aromatic quinoline intermediates and biomimetic asymmetric reduction.
- Zhao, Zi-Biao,Li, Xiang,Chen, Mu-Wang,Wu, Bo,Zhou, Yong-Gui
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p. 1691 - 1695
(2020/11/03)
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- Sustainable synthesis of quinolines (pyridines) catalyzed by a cheap metal Mn(I)-NN complex catalyst
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This study represents the first example of a bidentate phosphine-free manganese(I)-NN complex catalyst for the synthesis of quinolines (pyridines) through acceptorless dehydrogenative condensation of various secondary alcohols with amino alcohols. The coupling reactions occurred at 3 mol% catalyst loading and 110°C, and tolerated diverse functional groups. Moderate to excellent yields ranging from 45% to 89% were achieved after 12 hr of reaction. The present protocol provides a concise and environmentally friendly method for the construction of heterocyclic compounds.
- Chai, Huining,Tan, Weiqiang,Lu, Yuanyuan,Zhang, Guangyao,Ma, Jiping
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- The synthesis of quinolines: via denitrogenative palladium-catalyzed cascade reaction of o -aminocinnamonitriles with arylhydrazines
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The first example of the palladium-catalyzed cascade reaction of o-aminocinnamonitriles with arylhydrazines has been achieved, providing an efficient synthetic pathway to access quinolines with moderate to good yields. Preliminary mechanistic experiments
- Chen, Jiuxi,Huang, Hang,Li, Renhao,Xie, Jing,Xu, Tong,Ye, Xueting
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p. 8586 - 8593
(2020/03/13)
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- Pd-Catalyzed Tandem Reaction of 2-Aminostyryl Nitriles with Arylboronic Acids: Synthesis of 2-Arylquinolines
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A novel palladium-catalyzed protocol for the synthesis of 2-arylquinolines via tandem reaction of 2-aminostyryl nitriles with arylboronic acids has been developed with good functional group tolerance. The presented approach offers a new synthetic pathway toward the core structures of 2-arylquinolines compared to classical condensation reaction of (E)-2-aminostyryl aryl ketones. Moreover, the present synthetic route could be readily scaled up to gram quantity without difficulty. Preliminary mechanistic experiments showed that this transformation involves a nucleophilic addition of aryl palladium species to the nitrile to generate an aryl ketone intermediate followed by an intramolecular cyclization and dehydration to quinoline ring.
- Xu, Tong,Shao, Yinlin,Dai, Ling,Yu, Shulin,Cheng, Tianxing,Chen, Jiuxi
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p. 13604 - 13614
(2019/10/16)
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- Facile synthesis of substituted quinolines by iron(iii)-catalyzed cascade reaction between anilines, aldehydes and nitroalkanes
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A library of substituted quinolines has been synthesized by the reaction of aldehydes, anilines and nitroalkanes using a catalytic amount of Fe(iii) chloride. The reaction is a simple, efficient, one-pot, three-component domino strategy in ambient air which afforded the products in high yields. A probable pathway of the reaction is a sequential aza-Henry reaction/cyclization/denitration. The use of commercially available chemicals as starting materials, an inexpensive metal catalyst, aerobic reaction conditions, tolerance of a wide range of functional groups, and operational simplicity are the notable advantages of this present protocol.
- Mahato, Sachinta,Mukherjee, Anindita,Santra, Sougata,Zyryanov, Grigory V.,Majee, Adinath
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p. 7907 - 7917
(2019/09/06)
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- N-Heterocyclic carbene copper catalyzed quinoline synthesis from 2-aminobenzyl alcohols and ketones using DMSO as an oxidant at room temperature
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A facile and practical process for the synthesis of quinolines through an N-heterocyclic carbene copper catalyzed indirect Friedl?nder reaction from 2-aminobenzyl alcohol and aryl ketones using DMSO as an oxidant at room temperature is reported. A series of quinolines were synthesized in acceptable yields.
- Xu, Jingxiu,Chen, Qingmao,Luo, Zhigao,Tang, Xiaodong,Zhao, Jinwu
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p. 28764 - 28767
(2019/09/30)
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- Copper-Catalyzed Aerobic Oxidative Cyclization of Anilines, Aryl Methyl Ketones and DMSO: Efficient Assembly of 2-Arylquinolines
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A Cu-catalyzed C?H cyclization of simple anilines with ketones and DMSO as a one-carbon source has been developed. Using an aerobic oxidative protocol, a number of ketones and anilines could be easily converted to 2-arylquinolines, rather than 4-arylquinolines, thus providing a highly atom-economical and simple approach to biologically significant 2-arylquinolines. Based on the preliminary experiments, a plausible mechanism is proposed. (Figure presented.).
- Liu, Yufeng,Hu, Yuqun,Cao, Zhongzhong,Zhan, Xi,Luo, Weiping,Liu, Qiang,Guo, Cancheng
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supporting information
p. 2691 - 2695
(2018/06/04)
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- Synthesis of 2-Substituted Quinolines from 2-Aminostyryl Ketones Using Iodide as a Catalyst
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A new protocol for the synthesis of 2-substituted quinolines from 2-aminostyryl ketones has been developed using iodide as a nucleophilic catalyst. Conjugate addition of iodide to 2-aminostyryl ketones yielded the corresponding β-iodoketones, which could have a conformation where the amino and carbonyl groups are proximal through free rotation about the Cα-Cβ single bond. Subsequent condensation between the amino and carbonyl groups followed by elimination of hydrogen iodide provided the corresponding quinolines, with regeneration of the iodide catalyst.
- Lee, So Young,Jeon, Jiye,Cheon, Cheol-Hong
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p. 5177 - 5186
(2018/05/15)
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- On-Water Synthesis of 2-Substituted Quinolines from 2-Aminochalcones Using Benzylamine as the Nucleophilic Catalyst
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On-water synthesis of 2-substituted quinolines from 2-aminochalcone derivatives was developed using benzylamine as the nucleophilic catalyst. Various 2-aminochalcones could be applied to this protocol, and the desired 2-substituted quinoline products were isolated in excellent yields by simple filtration. Furthermore, we elucidated the role of benzylamine in this transformation and provided the detailed reaction mechanism. This protocol has several additional advantages, such as simple operation, broad substrate scope, good functional group tolerance, easy product isolation, recycling of the catalyst, and gram-scale synthesis.
- Lee, So Young,Cheon, Cheol-Hong
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p. 13036 - 13044
(2018/11/20)
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- Enantioselective Synthesis of Tetrahydroquinolines from 2-Aminochalcones via a Consecutive One-Pot Reaction Catalyzed by Chiral Phosphoric Acid
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A new asymmetric protocol for the synthesis of chiral tetrahydroquinolines from 2-aminochalcones via a two-step one-pot consecutive process (cyclization/asymmetric reduction) has been developed using chiral phosphoric acid as the sole catalyst. 2-Aminochalcones were converted into the corresponding quinolines through chiral phosphoric acid-catalyzed dehydrative cyclization, and the resultant quinolines were subsequently reduced to the chiral tetrahydroquinolines via chiral phosphoric acid-catalyzed asymmetric reduction with Hantzsch ester. Various 2-aminochalcones could be applicable to this protocol, and the desired tetrahydroquinolines were obtained in excellent yields and with excellent enantioselectivities. Furthermore, the utility of this protocol has been successfully demonstrated in the highly efficient synthesis of estrogen receptor modulator.
- Park, Do Young,Lee, So Young,Jeon, Jiye,Cheon, Cheol-Hong
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p. 12486 - 12495
(2018/10/24)
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- Palladium-catalyzed synthesis of quinolines from allyl alcohols and anilines
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A process for quinoline synthesis through palladium-catalyzed oxidative cyclization of aryl allyl alcohols and anilines is described. This process works in the absence of acid, base and any other additive and has a broad substrate scope, tolerating electron-withdrawing groups such as nitryl, trifluoromethyl and so on. A series of quinolines are prepared in satisfactory yields.
- Xu, Jingxiu,Sun, Jing,Zhao, Jinwu,Huang, Bin,Li, Xiaohan,Sun, Yulun
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p. 36242 - 36245
(2017/08/02)
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- Method for synthesizing quinoline derivative
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The invention discloses a method for synthesizing a quinoline derivative. The method comprises the specific steps of in a reaction container, adding ketone, aminobenzylmethanol, an iridium complex catalyst, alkaline and a solvent (water), carrying out reflux reaction on reaction mixture in air, and cooling to room temperature after reaction is ended; extracting by using ethyl acetate, carrying out rotary evaporation to remove a solvent, and then carrying out column separation to obtain a target compound. According to the method disclosed by the invention, a hydrogen binding agent or oxygen does not need to be used, the environment-friendly water is used as the reaction solvent and reflux is carried out for 12 hours in air. The reaction conforms to the requirement of green chemistry, so that the application prospect is wide.
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Paragraph 0126; 0127; 0128
(2017/12/27)
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- Coupling N-H Deprotonation, C-H Activation, and Oxidation: Metal-Free C(sp3)-H Aminations with Unprotected Anilines
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An intramolecular oxidative C(sp3)-H amination from unprotected anilines and C(sp3)-H bonds readily occurs under mild conditions using t-BuOK, molecular oxygen and N,N-dimethylformamide (DMF). Success of this process, which requires mildly acidic N-H bonds and an activated C(sp3)-H bond (BDE 85 kcal/mol), stems from synergy between basic, radical, and oxidizing species working together to promote a coordinated sequence of deprotonation: H atom transfer and oxidation that forges a new C-N bond. This process is applicable for the synthesis of a wide variety of N-heterocycles, ranging from small molecules to extended aromatics without the need for transition metals or strong oxidants. Computational results reveal the mechanistic details and energy landscape for the sequence of individual steps that comprise this reaction cascade. The importance of base in this process stems from the much greater acidity of transition state and product for the 2c,3e C-N bond formation relative to the reactant. In this scenario, selective deprotonation provides the driving force for the process.
- Evoniuk, Christopher J.,Gomes, Gabriel Dos Passos,Hill, Sean P.,Fujita, Satoshi,Hanson, Kenneth,Alabugin, Igor V.
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supporting information
p. 16210 - 16221
(2017/11/22)
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- Coupling Radical Homoallylic Expansions with C-C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals
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Selective addition of radicals to isonitriles can be harnessed for initiating reaction cascades designed to overcome the stereoelectronic restrictions on homoallylic ring expansion in alkyne reactions and to develop a new general route for the preparation of N-heteroaromatics. This method utilizes alkenes as synthetic equivalents of alkynes by coupling homoallylic ring expansion to yield the formal "6-endo" products with aromatization via stereoelectronically assisted C-C bond scission. Computational analysis of the homoallyic expansion potential energy surface reveals that the indirect 5-exo/3-exo/retro-3-exo path is faster than the direct 6-endo-trig closure, revealing the general exo-preference for the cyclization processes.
- Evoniuk, Christopher J.,Gomes, Gabriel Dos Passos,Ly, Michelle,White, Frankie D.,Alabugin, Igor V.
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p. 4265 - 4278
(2017/04/27)
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- Synthesis of quinolines through copper-catalyzed intermolecular cyclization reaction from anilines and terminal acetylene esters
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A simple and convenient copper-catalyzed intermolecular cyclization reaction for the synthesis of quinolines from anilines and terminal acetylene esters has been developed. This methodology constructs the C-N and C-C bonds successively via a cascade process, and provides the desired products in moderate to good yields.
- Zheng, Zhilei,Deng, Guobo,Liang, Yun
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p. 103478 - 103481
(2016/11/13)
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- Palladium-Catalyzed Allylic C-H Oxidative Annulation for Assembly of Functionalized 2-Substituted Quinoline Derivatives
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An efficient and practical palladium-catalyzed aerobic oxidative approach to afford functionalized 2-substituted quinolines in moderate to good yields from readily available allylbenzenes with aniline is developed. The present annulation process has high functional-group tolerance and high atom economy, making it a valuable and practical method in synthetic and medicinal chemistry. Moreover, this transformation is supposed to proceed through oxidation of allylic C-H functionalization to form C-C and C-N bonds in one pot.
- Li, Chunsheng,Li, Jianxiao,An, Yanni,Peng, Jianwen,Wu, Wanqing,Jiang, Huanfeng
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p. 12189 - 12196
(2016/12/23)
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- Acceptorless Dehydrogenative Cyclization of o-Aminobenzyl Alcohols with Ketones to Quinolines in Water Catalyzed by Water-Soluble Metal-Ligand Bifunctional Catalyst [Cp?(6,6′-(OH)2bpy)(H2O)][OTf]2
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The strategy for acceptorless dehydrogenative cyclization of o-aminobenzyl alcohols with ketones to quinolines in water has been accomplished. In the presence of [Cp?Ir(6,6′-(OH)2bpy)(H2O)][OTf]2, a series of desirable products were obtained in high yields. Notably, this research exhibits the potential for the construction of heterocycles via acceptorless dehydrogenative reactions in water catalyzed by water-soluble metal-ligand bifunctional catalysts.
- Wang, Rongzhou,Fan, Hongjun,Zhao, Wei,Li, Feng
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supporting information
p. 3558 - 3561
(2016/08/16)
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- Double C-H amination by consecutive SET oxidations
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A new method for intramolecular C-H oxidative amination is based on a FeCl3-mediated oxidative reaction of anilines with activated sp3 C-H bonds. The amino group plays multiple roles in the reaction cascade: (1) as the activating group in single-electron-transfer (SET) oxidation process, (2) as a directing group in benzylic/allylic C-H activation at a remote position, and (3) internal nucleophile trapping reactive intermediates formed from the C-H activation steps. These multielectron oxidation reactions proceed with catalytic amounts of Fe(iii) and inexpensive reagents.
- Evoniuk, Christopher J.,Hill, Sean P.,Hanson, Kenneth,Alabugin, Igor V.
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supporting information
p. 7138 - 7141
(2016/06/09)
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- Coupling cyclizations with fragmentations for the preparation of heteroaromatics: Quinolines from o-alkenyl arylisocyanides and boronic acids
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Stereoelectronic restrictions on homoallylic ring expansion in alkyne cascades can be overcome by using alkenes as synthetic equivalents of alkynes in reaction cascades that are terminated by C-C bond fragmentation. Implementation of this approach using Mn(iii)-mediated reaction of o-alkenyl isocyanides and boronic acids leads to efficient synthesis of substituted quinolines.
- Evoniuk, Christopher J.,Ly, Michelle,Alabugin, Igor V.
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supporting information
p. 12831 - 12834
(2015/08/06)
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- Synthesis of 2-substituted quinolines from alcohols
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A facile and economic method for the construction of 2-substituted quinolines by AgOTf-catalyzed 2-aminobenzyl alcohol and alkyne/ketone or 2-aminophenethyl alcohol and aldehyde has been developed. The electronic properties of the substituents on the alkyne, ketone, and aldehyde were investigated. It was found that molecules with both electron-donating and -withdrawing substituents were perfectly suitable substrates for this transformation, and the expected products were obtained in moderate to excellent yields. Moreover, the use of inexpensive starting materials and environmentally benign oxidants makes this atom efficient method particularly attractive.
- Xu, Xuefeng,Zhang, Xu,Liu, Wenming,Zhao, Qiang,Wang, Zhiqiang,Yu, Lintao,Shi, Fu
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supporting information
p. 3790 - 3792
(2015/06/08)
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- Synthesis of substituted quinoline via copper-catalyzed one-pot cascade reactions of 2-bromobenzaldehydes with aryl methyl ketones and aqueous ammonia
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In this Letter, a new version of the Friedl?nder synthesis of quinoline derivatives starting from 2-bromobenzaldehydes, aryl methyl ketones, and aqueous ammonia with copper-catalyzed amination as a key step is presented. Remarkable advantages of this new quinoline synthesis include commercially available and economical starting materials, simple operational process, and excellent efficiency.
- Li, Bin,Guo, Chenhao,Fan, Xuesen,Zhang, Ju,Zhang, Xinying
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supporting information
p. 5944 - 5948
(2015/01/08)
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- Synthetic utility of propylphosphonic anhydridedmso media: An efficient one-pot three-component synthesis of 2-arylquinolines
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Propylphosphonic anhydride (T3P?)DMSO-mediated onepot three-component synthesis which provides 2-arylquinolines in a single step from benzyl alcohols, anilines, and ethyl vinyl ether by the modified Povarov reaction has been demonstrated. T3P?DMSO is a mild and low-toxic peptide coupling agent and an easy to handle reagent for bulk reactions at room temperature.
- Narasimhamurthy, Kereyagalahally H.,Chandrappa, Siddappa,Kumar, Kothanahally S. Sharath,Swaroop, Toreshettahally R.,Rangappa, Kanchugarakoppal S.
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supporting information
p. 1073 - 1075
(2013/09/24)
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- Simple C-2-substituted quinolines and their anticancer activity
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Sixteen C-2-substituted quinolines were tested in both human cancer cell lines (MCF-7, H-460 and SF-268) and normal cell lines (Vero and THP-1). Preliminary results indicate that 2-α-furyl- and 2-γ-pyridinyl quinoline derivatives 1, 13 and 14 are active against three human cancer cell lines and, at the same time, were devoid of cytotoxic effect on normal cells. Biological activity and SAR results were compared with different molecular descriptors determined in silico using online available software, in an attempt to show a relationship with the possible mode of action of these quinoline derivatives.
- Kouznetsov, Vladimir V.,Rojas Ruiz, Fernando A.,Vargas Mendez, Leonor Y.,Gupta, Mahabir P.
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p. 680 - 686
(2012/09/22)
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- Synthesis of quinolines by a solid acid-catalyzed microwave-assisted domino cyclization-aromatization approach
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A microwave-assisted solid acid-catalyzed synthesis of quinolines from anilines and cinnamaldehydes is described. Use of montmorillonite K-10 results in a one-pot process; the cyclization and oxidation steps readily take place in a domino approach. Reactions were completed in a matter of minutes and provided excellent yields. The efficient and ecofriendly catalyst and the convenience of the product isolation make this process an attractive alternative for the synthesis of these important heterocycles.
- De Paolis, Omar,Teixeira, Liliana,T?r?k, Béla
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experimental part
p. 2939 - 2942
(2009/07/26)
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- In vitro antifungal activity of polyfunctionalized 2-(hetero)arylquinolines prepared through imino Diels-Alder reactions
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Diverse polyfunctionalized quinolines, easily prepared using Lewis acid-catalyzed imino Diels-Alder reactions between corresponding aldimines, were tested for antifungal properties against standardized as well as clinical isolates of clinically important fungi. Among them, 4-pyridyl derivatives displayed the best activities mainly against dermatophytes. The activity appears not to be related neither to the lipophilicity nor to the basicity of compounds.
- Melendez Gomez, Carlos M.,Kouznetsov, Vladimir V.,Sortino, Maximiliano A.,Alvarez, Sandra L.,Zacchino, Susana A.
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experimental part
p. 7908 - 7920
(2009/04/11)
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- A Novel Approach to 2-Arylated Quinolines: Electrocyclization of Alkynyl Imines via Vinylidene Complexes
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(Matrix presented) Alkynyl imines underwent [4 + 2] electrocyclization in the presence of 20 mol % W(CO)5(THF) to give 2-arylated quinolines in good yields. A deuterium labeling study suggests that the reaction proceeds via a tungsten vinylidene complex.
- Sangu, Kenichiro,Fuchibe, Kohei,Akiyama, Takahiko
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p. 353 - 355
(2007/10/03)
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