- Highly efficient and spectrally stable white organic light-emitting diodes using new red heteroleptic Iridium(III) complexes
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Highly efficient red phosphorescent iridium(III) complexes, (MPQ)2Ir(Pppy) and (MPQ)2Ir(TMSppy) based on 4-methyl-2-phenylquinoline (MPQ) as a cyclometalated main ligand and 2-[(1,1′-biphenyl)4-yl]pyridine (Pppy) or 2-[4-(trimethylsi
- Kim, Hee Un,Jang, Jae-Ho,Park, Hea Jung,Jung, Byung Jun,Song, Wook,Lee, Jun Yeob,Hwang, Do-Hoon
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Read Online
- Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines
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Visible-light-excited 9,10-phenanthrenequinone (PQ*) was used as a photocatalyst for the synthesis of polysubstituted quinolines via the electrocyclization of 2-vinylarylimines. Up to quantitative yields of 2,4-disubstituted quinolines were received after 1 h of excitation with blue LEDs at room temperature when MgCO3 was used as an additive in DCM. On the basis of experimental and DFT studies, we propose that PQ? induces one-electron oxidation of the imine substrate that triggers the electrocyclization mechanism.
- Talvitie, Juulia,Alanko, Iida,Bulatov, Evgeny,Koivula, Juho,P?ll?nen, Topias,Helaja, Juho
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p. 274 - 278
(2022/01/04)
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- Cobalt-catalyzed cross-coupling of nitrogen-containing heterocyclic phosphonium salts with arylmagnesium reagents
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Cobalt-catalyzed cross-couplings of nitrogen-containing heterocyclic phosphonium salts with arylmagnesium halides proceeded efficiently with the aid of cobalt(II) catalyst and copper(I) salt in tetrahydrofuran at ambient temperature, producing the desired
- Cui, Yan-Ying,Na, Jin-He,Guo, Meng-Meng,Huang, Jie-Ying,Chu, Xue-Qiang,Rao, Weidong,Shen, Zhi-Liang
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supporting information
(2022/02/16)
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- Carbocatalytic Cascade Synthesis of Polysubstituted Quinolines from Aldehydes and 2-Vinyl Anilines
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Oxidized active carbon (oAC) catalyses the formation of polysubstituted quinolines from o-vinyl anilines and aldehydes. The reaction proceeds in a cascade manner through condensation, electrocyclization and dehydrogenation, and gives access to a wide range of quinolines with alkyl and/or aryl substituents as demonstrated with 40 examples. The metal-free catalytic procedure allows a heterogeneous protocol for the synthesis of various polysubstituted quinolines. The mechanistic studies imply that both the acid and quinoidic groups in oAC are integral for the catalytic manifold. (Figure presented.).
- Bulatov, Evgeny,Helaja, Juho,Hu, Tao,Lenarda, Anna,M?kel?, Mikko K.,Malinen, Kiia,Melchionna, Michele,Nieger, Martin,Talvitie, Juulia,Wirtanen, Tom
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p. 3775 - 3782
(2021/07/20)
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- Magnetite (Fe3O4) nanoparticles-supported dodecylbenzenesulfonic acid as a highly efficient and green heterogeneous catalyst for the synthesis of substituted quinolines and 1-amidoalkyl-2-naphthol derivatives
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Abstract: Magnetically retrievable, magnetite (Fe3O4) nanoparticles-supported dodecylbenzenesulfonic acid (DDBSA@MNP) was synthesized and characterized through different analytical techniques such as TEM, XRD, FTIR, TGA, SEM, EDX and
- Katheriya, Deepak,Patel, Nipun,Dadhania, Harsh,Dadhania, Abhishek
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p. 805 - 816
(2020/10/02)
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- Novel anti-solvent quenching near-infrared two-zone dye and preparation method thereof Preparation method and application thereof
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The invention provides a novel anti-solvent quenching near-infrared two-zone dye and a preparation method and application thereof, and relates to a novel anti-solvent quenching NIR-II dye containing a nitrogen heterocyclic ring. Experiments show that the
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Paragraph 0031-0037
(2021/11/26)
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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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- 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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- [(PPh3)2NiCl2]-Catalyzed C-N bond formation reaction via borrowing hydrogen strategy: Access to diverse secondary amines and quinolines
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Commercially available [(PPh3)2NiCl2] was found to be an efficient catalyst for the mono-N-alkylation of (hetero)- A romatic amines, employing alcohols to deliver diverse secondary amines, including the drug intermediates chloropyramine (5b) and mepyramine (5c), in excellent yields (up to 97%) via the borrowing hydrogen strategy. This method shows a superior activity (TON up to 10000) with a broad substrate scope at a low catalyst loading of 1 mol % and a short reaction time. Further, this strategy is also successful in accessing various quinoline derivatives following the acceptorless dehydrogenation pathway.
- Donthireddy,Pandey, Vipin K.,Rit, Arnab
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p. 6994 - 7001
(2021/06/09)
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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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- Visible-Light Photoredox Alkylation of Heteroaromatic Bases Using Ethyl Acetate as Alkylating Agent
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An efficient room-temperature visible-light photoredox α-acyloxyalkylation reaction of N-heteroarenes is reported, which relies on the use of ethyl acetate as a cheap and non-conventional radical source. The direct C(sp2)-C(sp3) coupling was extended to a diverse set of mono-, bi-, and tricyclic of N-heteroaromatics, and the optimized photoredox protocol was successfully performed on a multigram scale. The scope of the alkylating agent was also explored and a plausible mechanism was proposed, involving photoinduced single-electron transfer and hydrogen-atom transfer processes.
- Gy?rfi, Nándor,Kotschy, András,Gyuris, Márió
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supporting information
p. 6447 - 6454
(2020/10/22)
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- Preparation of 2-Arylquinolines from 2-Arylethyl Bromides and Aromatic Nitriles with Magnesium and N -Iodosuccinimide
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Treatment of 2-arylethylmagnesium bromides, prepared from 2-arylethyl bromides and magnesium, with aromatic nitriles, followed by reaction with water and then with N -iodosuccinimide under irradiation with a tungsten lamp, gave the corresponding 2-arylquinolines in good to moderate yields under transition-metal-free conditions. 2-Alkylquinolines could be also obtained in moderate yields by the same procedure with 2-arylethyl bromides, magnesium, aliphatic nitriles bearing a secondary alkyl group, and N -iodosuccinimide.
- Naruto, Hiroki,Togo, Hideo
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p. 1122 - 1130
(2020/04/01)
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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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- Mn(III)-Mediated Regioselective 6-endo-trig Radical Cyclization of o-Vinylaryl Isocyanides to Access 2-Functionalized Quinolines
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A Mn(III)-mediated radical cyclization reaction of o-vinylaryl isocyanides and arylboronic acids or diphenylphosphine oxides to access various 2-functionalized quinolines under mild conditions was developed. With the introduction of radical stabilizing substituents (e. g. aryl and methyl group) on vinyl group, this reaction provides a regiospecific 6-endo-trig radical cyclization of o-vinylaryl isocyanides, giving a number of structurally unique and biologically potential 2-functionalized quinoline derivatives.
- Liu, Yan,Li, Shi-Jun,Chen, Xiao-Lan,Fan, Lu-Lu,Li, Xiao-Yun,Zhu, Shan-Shan,Qu, Ling-Bo,Yu, Bing
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p. 688 - 694
(2020/01/02)
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- Quinoline compound and synthesis method thereof
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The invention discloses a synthesis method of a quinoline compound. The synthesis method comprises the following steps: adding a diazocarbonyl compound and a 2-vinylaniline compound into a solvent, carrying out a reaction under the protection of an inert
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Paragraph 0094-0099
(2020/02/14)
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- Regiodivergent C-H Alkylation of Quinolines with Alkenes by Half-Sandwich Rare-Earth Catalysts
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The regiodivergent catalysis of C-H alkylation with alkenes is of great interest and importance but has remained hardly explored to date. We report herein the first regiodivergent C-H alkylation of quinolines with alkenes by half-sandwich rare-earth catal
- Lou, Shao-Jie,Zhang, Liang,Luo, Yong,Nishiura, Masayoshi,Luo, Gen,Luo, Yi,Hou, Zhaomin
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supporting information
p. 18128 - 18137
(2020/12/02)
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- Superbase-Mediated Indirect Friedl?nder Reaction: A Transition Metal-Free Oxidative Annulation toward Functionalized Quinolines
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A superbase mediated indirect Friedl?nder reaction towards functionalized quinolines has been realized. The reaction was performed with o-aminobenzyl alcohol and ketones having an active methylene moiety in the presence of KOH and in DMSO. The reaction proceeds predominantly via initial formation of an imine intermediate and subsequent oxidation of the benzyl alcohol functionality and condensation to afford substituted quinolines. We could also demonstrate that a minor fraction of the reaction proceeds via a chalcone intermediate. The transition metal-free oxidative annulation was found to be general affording 2-substituted, 2,3-disubstituted/fused or multi-substituted quinolines. The reaction was extended towards the functionalization of natural products and the applicability of the reaction for gram-scale synthesis of quinolines was also demonstrated.
- Rahul,Nitha,Omanakuttan, Vishnu K.,Babu, Sheba Ann,Sasikumar,Praveen, Vakayil K.,Hopf, Henning,John, Jubi
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p. 3081 - 3089
(2020/05/08)
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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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- Arylquinoline derivative synthesis method
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The invention belongs to the technical field of organic synthesis, and specifically relates to an arylquinoline derivative synthesis method, wherein the synthesis of arylquinoline derivatives with diversified structures is achieved through palladium-catalyzed continuous carbon-carbon/carbon-nitrogen bond construction, and specifically a 2-arylquinoline derivative is prepared by using a compound (E)-3-(2-aniline)acrylonitrile and arylboronic acid as raw materials under a palladium catalyst system. According to the present invention, the method has characteristics of wide raw material source oreasy preparation, simple operation, controllable selectivity, high yield, mild conditions and wide applicability.
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Paragraph 0057-0060
(2019/11/29)
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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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- Rh(iii)-catalyzed alkynylation: Synthesis of functionalized quinolines from aminohydrazones
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Rhodium-catalyzed, chemo- and regioselective synthesis of functionalized quinolines using 2-aminohydrazones and terminal alkynes has been described. The reaction is oxidant/base-free and tolerates a wide variety of functional groups and has been successfu
- Kumar, Pradeep,Garg, Vineeta,Kumar, Manoj,Verma, Akhilesh K.
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supporting information
p. 12168 - 12171
(2019/10/22)
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- Introduction of Heteroaromatic Bases onto Cycloalkanes with BPO
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Heteroaromatic bases, such as lepidine, phenanthridine, isoquinoline, etc., were treated with cycloalkanes, such as cyclopentane, cyclohexane, cycloheptane, cyclooctane, etc., under warming conditions with benzoyl peroxide (BPO) to form heteroaromatic bases bearing cycloalkyl groups in good yields. Here, the inert C(sp3)-H bond of cycloalkanes could be functionalized to C(sp3)-heteroaromatic bases via an oxidative radical reaction pathway under transition-metal-free conditions.
- Zhou, Luan,Togo, Hideo
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p. 1627 - 1634
(2019/02/19)
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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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- Synthesis of Quinolines Through Acceptorless Dehydrogenative Coupling Catalyzed by Rhenium PN(H)P Complexes
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A practical and sustainable synthesis of substituted quinolines was achieved through the annulation of 2-aminobenzyl alcohol with various secondary alcohols, ketones, aldehydes, or nitriles, under hydrogen-borrowing conditions. Under the catalysis of well-defined rhenium complexes bearing tridentate diphosphinoamino ligands, the reaction proceeded efficiently (31 examples were isolated with yields up to 96 %) affording a variety of quinoline derivatives.
- Wei, Duo,Dorcet, Vincent,Darcel, Christophe,Sortais, Jean-Baptiste
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p. 3078 - 3082
(2019/01/24)
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- Ligand-controlled phosphine-free Co(II)-catalysed cross-coupling of secondary and primary alcohols
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Cobalt(II) complexes (5 mol% Co) bearing phosphine-free N?N?N pincer ligands efficiently catalyze C–C coupling of secondary and primary alcohols to selectively form α-alkylated ketones with a good functional group compatibility using NaOH (20 mol%) as a base at 120 °C. The NH group on the N?N?N–Co(II) precatalyst controls the activity and selectivity. This simple catalytic system is involved in the synthesis of quinolones via the dehydrogenative annulation of 2-aminobenzyl alcohols with secondary alcohols.
- Zhang, Shi-Qi,Guo, Bin,Xu, Ze,Li, Hong-Xi,Li, Hai-Yan,Lang, Jian-Ping
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- Phosphine Ligand-Free Ruthenium Complexes as Efficient Catalysts for the Synthesis of Quinolines and Pyridines by Acceptorless Dehydrogenative Coupling Reactions
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A series of phosphine-free Ru(III)/Ru(II) complexes of NH functionalized N?N?N pincer ligands exhibit excellent activity for acceptorless dehydrogenative coupling (ADC) of secondary alcohols with 2-aminobenzyl or γ-amino alcohols to quinolines and pyridines. Ru(III) complexes [LRuCl3] (L=6-(3-R1,5-R2-1H-pyrazol-1-yl)-N-(pyridin-2-yl)pyridin-2-amine; 1 a: R1=R2=H (L1); 1 b: R1=R2=Me (L2); 1 c: R1=H, R2=CF3 (L3); 1 d: R1=H, R2=Ph (L4); 1bMe: L=6-(3,5-dimethyl-1H-pyrazol-1-yl)-N-methyl-N-(pyridin-2-yl)pyridin-2-amine (L2Me)) were obtained by refluxing RuCl3 ? xH2O with the corresponding ligand in EtOH. Five Ru(II) complexes [LRu(DMSO-κS)Cl2] (2 a: L=L1; 2 b: L=L2; 2 c: L=L3; 2 d: L=L4; 2bMe: L=L2Me) were formed by reducing the corresponding Ru(III) complex in refluxing EtOH. The latter complexes could also be prepared directly by refluxing Ru(DMSO)4Cl2 with the corresponding ligand in EtOH. These Ru(III) and Ru(II) complexes, especially 1 b/2 b, exhibited high catalytic efficiency and broad functional group tolerance in ADC reactions of secondary alcohols with 2-aminobenzyl or γ-amino alcohols to quinolines and pyridines. A detail mechanistic study indicated the Ru(III) complex was reduced into the Ru(II) species, which is the active catalytic center for ADC via a Ru?H/N?H bifunctional outer-sphere mechanism. This protocol provides a reliable, atom-economical and environmentally benign procedure for C?N and C?C bond formation.
- Guo, Bin,Yu, Tian-Qi,Li, Hong-Xi,Zhang, Shi-Qi,Braunstein, Pierre,Young, David J.,Li, Hai-Yan,Lang, Jian-Ping
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p. 2500 - 2510
(2019/05/10)
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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 multi-functionalized quinolines and 1,2-dihydroquinolines through FeCl3-mediated reactions of carbonyl compounds with 2-vinylanilines
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A facile and efficient approach toward the synthesis of functionalized quinolines and 1,2-dihydroquinolines from carbonyl compounds and 2-vinylanilines is described. The protocol utilizes the nonhazardous and less expensive FeCl3 as catalyst wi
- Liu, Sha,Li, Gaoqiang,Xu, Feng
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p. 888 - 892
(2018/07/25)
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- Decarbonylative Methylation of Aromatic Esters by a Nickel Catalyst
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A Ni-catalyzed decarbonylative methylation of aromatic esters was achieved using methylaluminums as methylating agents. Dimethylaluminum chlorides uniquely worked as the methyl source. Because of the Lewis acidity of aluminum reagents, less reactive alkyl esters could also undergo the present methylation. By controlling the Lewis acidity of aluminum reagents, a chemoselective decarbonylative cross-coupling between alkyl esters and phenyl esters was successful.
- Okita, Toshimasa,Muto, Kei,Yamaguchi, Junichiro
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p. 3132 - 3135
(2018/05/28)
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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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- Quantitative structure activity relationship and biological activity studies of 4-methyl-2-(4-substituted phenyl)quinoline derivatives
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Quantitative structure activity relationship (QSAR) studies of some 4-methyl-2-(4-substituted phenyl)quinoline derivatives were carried out to determine their predicted biological activities. Numbers of descriptors were tested to adjudge a quantitative correlation between activity and structural features using training set and test set. Significant correlation was observed between activities and descriptors. The results were interpreted on the basis of linear regression analysis. Experimental antibacterial activities of the test set compounds were determined. The predicted biological activities generated by QSAR model were compared with the experimental antibacterial activities. The concurrence between the predicted and experimental biological activities validates the QSAR model. Thus, it can be concluded that the model under the present investigation can be applied for predicting the unknown biological activities of structurally similar molecules.
- Rahangdale,Inam,Chourasia
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p. 479 - 482
(2018/02/09)
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- Direct arylation for the synthesis of 2-arylquinolines from N-methoxyquinoline-1-ium tetrafluoroborate salts and arylboronic acids
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A rapid and direct arylation reaction of N-methoxyquinoline-1-ium tetrafluoroborate derivatives and arylboronic acids with high regioselectivety at room temperature was discovered. The reaction shows exceptional functional group tolerance and broad substrate scope regarding both the quinoline derivatives and the arylboronic acids.
- Ren, Xiaoxiao,Han, Shuaijun,Gao, Xianying,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
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p. 1065 - 1068
(2018/02/19)
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- Ionic liquid as an efficient medium for the synthesis of quinoline derivatives via α-chymotrypsin-catalyzed friedl?nder condensation
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An efficient, convenient, and eco-friendly biocatalytic approach was developed for the synthesis of quinoline derivatives via the α-chymotrypsin-catalyzed Friedl?nder reaction. Interestingly, α-chymotrypsin exhibited higher catalytic activity in an ionic
- Le, Zhang-Gao,Liang, Meng,Chen, Zhong-Sheng,Zhang, Sui-Hong,Xie, Zong-Bo
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supporting information
(2017/06/08)
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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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p. 16210 - 16221
(2017/11/22)
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- Palladium-Catalyzed [5+1] Annulation of 2-(1-Arylvinyl) Anilines and α-Diazocarbonyl Compounds toward Multi-functionalized Quinolines
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A palladium-catalyzed [5+1] annulation of 2-(1-arylvinyl) anilines and α-diazocarbonyl compounds has been developed, affording a series of multi-functionalized quinolines in moderate to good yields. This procedure proceeded with the sequential insertion o
- Zhu, Jiawei,Hu, Weiming,Sun, Song,Yu, Jin-Tao,Cheng, Jiang
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p. 3725 - 3728
(2017/09/25)
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- A method for the synthesis of quinoline derivatives
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The invention belongs to the technical field of organic synthesis and particularly relates to a synthesis method of quinoline derivatives. The synthesis method comprises the steps of sequentially adding aromatic amine, aldehyde and alcohol into a reaction
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Paragraph 0079-0081
(2017/08/23)
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- The photochemical alkylation and reduction of heteroarenes
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The functionalization of heteroarenes has been integral to the structural diversification of medicinally active molecules such as quinolines, pyridines, and phenanthridines. Electron-deficient heteroarenes are electronically compatible to react with relatively nucleophilic free radicals such as hydroxyalkyl. However, the radical functionalization of such heteroarenes has been marked by the use of transition-metal catalyzed processes that require initiators and stoichiometric oxidants. Herein, we describe the photochemical alkylation of quinolines, pyridines and phenanthridines, where through direct excitation of the protonated heterocycle, alcohols and ethers, such as methanol and THF, can serve as alkylating agents. We also report the discovery of a photochemical reduction of these heteroarenes using only iPrOH and HCl. Mechanistic studies to elucidate the underlying mechanism of these transformations, and preliminary results on catalytic methylations are also reported.
- McCallum,Pitre,Morin,Scaiano,Barriault
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p. 7412 - 7418
(2017/10/31)
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- Simple and Clean Photo-induced Methylation of Heteroarenes with MeOH
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Heteroarene methylation utilizing a cheap and safe methylation source without involving transition metals represents an important yet challenging objective. Here, a simple and clean catalyst-free protocol for the methylation of various heteroarenes (including six- and five-membered types) is described under light irradiation. This protocol employs cheap, readily available, and abundant MeOH as both the solvent and the methylation source. It was found that adding dichloromethane (DCM) as a co-solvent could significantly increase the yield of the methylation products. Heteroarenes bearing various functional groups could be methylated and tri-deuteromethylated successfully. Deuterium labeling studies suggested that the newly generated methyl group in the products consisted of two hydrogens from the methyl group and one hydrogen from the OH group in MeOH.
- Liu, Wenbo,Yang, Xiaobo,Zhou, Zhong-Zhen,Li, Chao-Jun
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supporting information
p. 688 - 702
(2017/05/15)
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- A method for utilizing the aromatic amine, aromatic aldehyde, synthesized of quinoline derivatives
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The invention provides a method for synthesizing a quinoline derivative by utilizing arylamine, aromatic aldehyde and ketone, and belongs to the technical field of the synthesis of the quinoline derivative. According to the method for synthesizing a quinoline derivative by utilizing arylamine, aromatic aldehyde and ketone, in the existence of silver trifluoromethanesulfonate and trifluoromethanesulfonic acid, the quinoline derivative is synthesized by virtue of the reaction of an arylamine compound, an aromatic aldehyde compound and ketone compound. A reaction general formula is as shown in the specification. Compared with the prior art, the method is not only applicable to a great amount of functional groups, but also is simple in operation, high in yield, single in product structure, convenient to separate and purify, safe, low in price and small in pollution.
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Paragraph 0042; 0043
(2018/01/11)
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- Ag-Catalyzed Intramolecular Sequential Vicinal Diamination of Alkynes with Isocyanates: Synthesis of Fused Indole-Cyclic Urea Derivatives
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A formal intramolecular vicinal 1,2-diamination of alkynes is achieved for the synthesis of indole-cyclic urea fused derivatives through a double cyclization process from readily available aminophenyl propargyl alcohols. This sequential triple C-N bond co
- Rajesh, Manda,Puri, Surendra,Kant, Ruchir,Sridhar Reddy, Maddi
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p. 5169 - 5177
(2017/05/24)
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- For catalytic synthesis of quinoline derivatives
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The invention discloses a quinoline derivative efficient catalytic synthesis method belonging to the technical field of organic synthesis. The molar ratio of an active alpha-methyl or methylene carbonyl compound and 2-amino acetophenone is 1: 1, the molar
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Paragraph 0035; 0036
(2017/02/24)
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- Silver-catalyzed three-component approach to quinolines starting from anilines, aldehydes, and alcohols
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A silver-catalyzed sequential formation of two C-C bonds for the construction of a series of polysubstituted quinolines from anilines, aldehydes, and alcohols under mild conditions has been developed. The transformation is effective for a broad range of substrates, including aliphatic alcohols, arylalkanols, cycloalkanols, and ethylene glycol, thereby permitting the expansion of the constituent architectures of the heterocyclic framework.
- Zhang, Xu,Liu, Wenmin,Sun, Ruixue,Xu, Xuefeng,Wang, Zhiqiang,Yan, Yanlei
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p. 1563 - 1568
(2016/06/14)
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- Iron-Catalyzed Cyclization of Nitrones with Geminal-Substituted Vinyl Acetates: A Direct [4 + 2] Assembly Strategy Leading to 2,4-Disubstituted Quinolines
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An iron-catalyzed intermolecular [4 + 2] cyclization of arylnitrones with geminal-substituted vinyl acetates was developed for the synthesis of 2,4-disubstituted quinolines in moderate to good yields with good functional group compatibilities. Preliminary mechanistic studies suggest a plausible iron-catalyzed C-H activation process under external-oxidant-free conditions.
- Zhong, Mingbing,Sun, Song,Cheng, Jiang,Shao, Ying
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p. 10825 - 10831
(2016/11/29)
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- Method for preparing 2-aryl-4-methyl quinoline compound
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The invention discloses a method for preparing a 2-aryl-4-methyl quinoline compound. The method comprises the following steps of: adding fluoride and an alkynyl imine compound into an organic solvent, and heating to react completely, wherein the structural formula of the alkynyl imine compound is as shown in the specification, and the structural formula of the 2-aryl-4-methyl quinoline compound is a shown in the specification, in the formulas, R1 is hydrogen, halogen, methyl, methoxyl, thiophene or cyanogen radical; R2 is hydrogen, methyl or methoxyl. Compared with the prior art, the 2-aryl-4-methyl quinoline compound can be prepared from one organism of the alkynyl imine compound under the action of the fluoride at one stime. The method disclosed by the invention is easy to operate and simple and convenient in aftertreatmnet, and the designability of substrates is good.
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Paragraph 0027; 0028; 0044; 0045; 0046; 0047
(2017/03/14)
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- Preparation method and application of pyridyl benzimidazole phenyl quinoline iridium (III) complex based on long carbon chain modification
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The invention relates to the technical field of organic photovoltaic materials, and specifically relates to a preparation method an application of a pyridyl benzimidazole phenyl quinoline iridium (III) complex based on long carbon chain modification, represented by the following general structural formula. The type of complex is composed of piperidine or morpholine cyclometal C^N bidentate ligand connected and substituted by methylene, central metal iridium ion and N-Cn (n=16-32) alkyl-2-(2-pyridyl)benzimidazole. The general structural formula is as the following. According to the invention, the methylene-substituted phenyl quinolone derivative C^N bidentate ligand is subjected to a reaction with iridium trichloride trihydrate, such that an iridium chloro-bridge dimer of the corresponding ligand is obtained; the dimer is further subjected to a reaction with N-Cn (n=16-32) alkyl-2-(2-pyridyl)benzimidazole; and iron exchange is carried out, such that the complex is prepared. The target iridium complex provided by the invention assists in effectively marking cell membranes. After protonation, complex water solubility is enhanced, such that the complex has a good application prospect in the fields of cell membrane pH value detection, imaging and marking.
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Paragraph 0024; 0025; 0026; 0027; 0028
(2016/10/08)
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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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- Metal free carboamination of internal alkynes - An easy access to polysubstituted quinolines
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A metal free carboamination of unactivated alkynes towards highly substituted quinolines was realized in the presence of a synergistic Br?nsted acid catalyst system. Supported by mechanistic probes, the reaction proceeds via a highly reactive vinyl cation in a C-C bond formation - Schmidt reaction sequence. The irreversible extrusion of N2, as a powerful driving force, allows for a general conversion of poorly nucleophilic aliphatic alkynes.
- Stopka,Niggemann
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supporting information
p. 5761 - 5764
(2016/05/19)
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- Revisiting the Gold-Catalyzed Dimerization of 2-Ethynylanilines: A Room-Temperature and Silver-Free Protocol for the Synthesis of Multifunctional Quinolines
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A room temperature and silver-free protocol for the formation of quinolines from 2-ethynylanilines through a dimerization event was achieved using a dinuclear gold catalyst, Au2(BIPHEP)(NTf2)2. The reaction is inherently modular, allowing for the incorporation of peripheral substituents at any site of the quinoline product. The reaction is readily applied to other heterocyles also as exemplified by the preparation of naphthyridines. Competition reactions to determine the reactivity of dissimilar alkynes demonstrated that the product ratio of dimerization vs intermolecular addition is rather dependent on the electronic nature of aryl substituent on the alkynes. However, control experiments with substrates possessing internal alkynes resulted in cycloisomerization instead of expected dimerization, which is indicative of possible steric influence of the alkyne terminus in the reaction outcome.
- Praveen, Chandrasekar,Perumal
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p. 855 - 864
(2016/03/15)
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