- Unusual product distribution from Friedlaender reaction of Di-and triacetylbenzenes with 3-aminonaphthalene-2-carbaldehyde and properties of new benzo[g]quinoline-derived Aza-aromatics
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The Friedlaender reactions of acetylbenzenes and 2-acetylpyridine with 3-aminonaphthalene-2-carbaldehyde afforded the corresponding 2-phenylbenzo[g]quinoline and 2-(pyrid-2-yl)benzo[g]quinoline, respectively. The same reactions of 3-aminonaphthalene-2-carbaldehyde with 1,2-, 1,3-, 1,4-di- and 1,3,5-triacetylbenzenes, however, afforded a series of corresponding (benzo[g]quinolin-2-yl)benzenes as new N,C-bidentate and unexpected benzo[g]quinoline. Crystallinity, thermal properties, absorption and emission spectral properties of the products were studied.
- Karim, Moinul,Jahng, Yurngdong
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- Near-infrared-emitting iridium(III) complexes as phosphorescent dyes for live cell imaging
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The three near-infrared-emitting cationic iridium(III) complexes [Ir(pbq-g)2(NaN)]+PF 6- (pbq-g = phenylbenzo[g]quinoline; N aN = bipyridine (1), 1,10-phenanthroline (2), 4,7-diphenyl-1,10-phenanthroline (3)) have been demonstrated as phosphorescent dyes in live cell imaging. These complexes with different ancillary ligands show similar near-infrared (NIR) emission with λmax,peak at 698 nm and λmax,shoulder at 760 nm in CH2Cl2 solutions, with a moderate quantum yield of around 3%. However, these complexes behave quite differently as NIR dyes for live cell imaging. Complexes 1 and 2 exhibit exclusive staining in the cytoplasm with good cell membrane permeability under excitation at 488 nm, while 3 gives almost no cell uptake, as further determined by flow cytometry. Although the lipophilicities of these complexes follow the order 1 a key role in the design of NIR-emitting iridium(III) complexes for practical applications in bioimaging.
- Zhang, Guoliang,Zhang, Huiyuan,Gao, Yuan,Tao, Ran,Xin, Lijun,Yi, Junyang,Li, Fuyou,Liu, Wanli,Qiao, Juan
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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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- 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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- Near-infrared emission electrostimulation response type iridium (III) complex as well as preparation method and application thereof
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The invention discloses a near-infrared emission electrostimulation response type iridium (III) complex and a preparation method and application thereof, wherein the iridium (III) complex is formed by combining a cyclometalC ^ ^ N ligand with a large conj
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Paragraph 0017-0018
(2021/10/20)
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- Dehydrogenative Synthesis of Quinolines, 2-Aminoquinolines, and Quinazolines Using Singlet Diradical Ni(II)-Catalysts
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Simple, straightforward, and atom economic methods for the synthesis of quinolines, 2-aminoquinolines, and quinazolines via biomimetic dehydrogenative condensation/coupling reactions, catalyzed by well-defined inexpensive and easy to prepare singlet diradical Ni(II)-catalysts featuring two antiferromagnetically coupled singlet diradical diamine type ligands are described. Various polysubstituted quinolines, 2-aminoquinolines, and quinazolines were synthesized in moderate to good yields from different low-cost and readily accessible starting materials. Several control experiments were carried out to get insight into the reaction mechanism which shows that the nickel and the coordinated diamine ligands participate in a synergistic way during the dehydrogenation of alcohols.
- Chakraborty, Gargi,Sikari, Rina,Das, Siuli,Mondal, Rakesh,Sinha, Suman,Banerjee, Seemika,Paul, Nanda D.
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p. 2626 - 2641
(2019/02/26)
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- A nickel catalyzed acceptorless dehydrogenative approach to quinolines
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A general, efficient and environmentally benign, one-step synthesis of substituted quinoline derivatives was achieved by acceptorless dehydrogenative coupling of o-aminobenzylalcohols with ketones and secondary alcohols catalyzed by a cheap, earth abundant and easy to prepare nickel catalyst [Ni(MeTAA)], featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)). A wide variety of substituted quinolines were synthesized in high yields starting from readily available o-aminobenzylalcohols and ketones or secondary alcohols. A few controlled reactions were carried out to establish the acceptorless dehydrogenative nature of the reactions.
- Parua, Seuli,Sikari, Rina,Sinha, Suman,Das, Siuli,Chakraborty, Gargi,Paul, Nanda D.
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p. 274 - 284
(2018/01/12)
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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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- 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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- A aryl heterocyclic compound and its preparation method and a kind of organic electroluminescent device (by machine translation)
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This invention has offered a kind of aromatic heterocyclic compound, the structure shown in formula (I). This invention is in the benzo [g] quinoxaline, benzo [g] quinoline and benzo [g] isoquinoline, and the like to introduce the structure R 1, R 2, R 3, electron density can be improved, to improve compound performance skills and upward, thus the formula (I) shown in a very good Arylheterocycle compound can be used as the electron transport material is applied, to its preparation of the organic electroluminescent light-emitting device with higher brightness, good heat resistance, long life and high luminous efficiency, and the like. (by machine translation)
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Paragraph 0201; 0202; 0205; 0206; 0207; 0209
(2016/10/08)
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- A method for the synthesis of substituted quinolines via electrophilic cyclization of 1-azido-2-(2-propynyl)benzene
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(Chemical Equation Presented) A new and efficient strategy for the synthesis of substituted quinolines via electrophilic cyclization is developed. The intramolecular cyclization of 1-azido-2-(2-propynyl)benzene 1 proceeds smoothly in the presence of electrophilic reagents (I2, Br 2 , ICl, NBS, NIS, and HNTf2) in CH3NO 2 at room temperature or in the presence of catalytic amounts of AuCl3/AgNTf2 in THF at 100 °C to afford the corresponding quinolines 2 in good to high yields. In the case of the electrophilic reagents, E of 2 is either I, Br, orH, depending on the reagent type, while E of 2 is H in the case of the electrophilic catalyst. 2010 American Chemical Society.
- Huo, Zhibao,Gridnev, Ilya D.,Yamamoto, Yoshinori
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supporting information; experimental part
p. 1266 - 1270
(2010/04/29)
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- Novel organic electroluminescent compounds and organic electroluminescent device using the same
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The present invention relates to novel organic electroluminescent compounds exhibiting high luminous efficiency, and organic electroluminescent devices comprising the same. The organic electroluminescent compounds according to the invention are characteri
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Page/Page column 53
(2009/09/26)
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- Novel aromatic N-oxyl radical based on the benzo[g]quinoline skeleton: Synthesis and intermolecular ferromagnetic interaction
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A novel stable organic radical, 2,2-diphenyl-1,2-dihydrobenzo[g]quinoline- N-oxyl (2), has been synthesized and structurally characterized in order to examine the ring extension effect on the known derivative, 2,2-diphenyl-1,2- dihydroquinoline-N-oxyl (1). Based on SQUID measurement, 2 exhibited a ferromagnetic interaction obeying the Bleaney-Bowers equation with 2J = +4.6 cm-1. The X-ray analysis revealed an intermolecular edge-edge association of the aryl ring and N-oxyl moiety in the crystal of 2. The bifurcated edge-edge contacts between the α-spin site (nitroxyl O atom) and the β-spin site (aryl-H atoms) are responsible for the ferromagnetic interaction of 2.
- Yao, Masaru,Inoue, Hidenari,Yoshioka, Naoki
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