- Nickel-catalyzed α-alkylation of ketones with benzyl alcohols
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We reported an efficient method for α-alkylation of ketones with benzyl alcohols using the pyridine-bridged pincer-type N-heterocyclic carbenes nickel complexes as catalysts. A wide range of ketones and benzyl alcohols were efficiently converted into various alkylated products in moderate to high yields. In addition, these nickel complexes were also successfully applied for the synthesis of a wide range of quinoline derivatives.
- Wu, Di,Wang, Yubin,Li, Min,Shi, Lei,Liu, Jichang,Liu, Ning
-
-
- Direct C-H Arylation and Alkylation of Electron-Deficient Heteroaromatic Compounds with Organozinc Reagents
-
A direct and convenient method for the C-H arylation and alkylation of electron-deficient N-heteroarenes with readily available organozinc reagents has been developed. This transformation could be readily performed in the absence of a transition-metal catalyst and external oxidants, affording a wide range of substituted heteroarenes with good functional group tolerance in good to excellent yields. The developed simple protocol is scalable to the gram level and suitable for late-stage modification of bioactive molecules and drugs.
- Peng, Zhihua,Yu, Chuanman,Wang, Yilei,Wei, Dongyue,Jiang, Cuiyu
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p. 3678 - 3688
(2021/11/16)
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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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- The preparation of a Co@C3N4catalyst and applications in the synthesis of quinolines from 2-aminobenzyl alcohols with ketones
-
An unsymmetrical diphenylphosphino-pyridinyl-triazole ligand was synthesized and characterized through IR, NMR and MS and the corresponding earth-abundant metal complex (cobalt) was prepared. Considering energy consumption and environmental friendliness, it is necessary to turn this diphenylphosphino-pyridinyl-triazole cobalt complex into a recyclable catalyst, which could easily be reused. Therefore, a heterogeneous catalyst was synthesized through Co-doping of C3N4, and the Co-nanoparticles on C3N4revealed high catalytic activity for the synthesis of quinolines with good recovery performance.
- Cao, Fei,Mao, Anruo,Yang, Bobin,Ge, Chenyang,Wang, Dawei
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supporting information
p. 6768 - 6772
(2021/04/22)
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- Organometal-Free Arylation and Arylation/Trifluoroacetylation of Quinolines by Their Reaction with CF3-ynones and Base-Induced Rearrangement
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The reaction of quinolines with CF3-ynones resulted in the formation of 1,3-oxazinoquinolines. Subsequent treatment of the reaction mixture with a base initiated deep structural transformation of primary products. Both steps proceed in very high yield. As a result, unusual rearrangement of 1,3-oxazinoquinolines to form either 2-arylquinolines or 2-aryl-3-trifluoroacetylquinolines was discovered. The decisive role of the base in the reaction direction was shown. Using these reactions, highly efficient pathways to 2-arylquinolines and 2-aryl-3-trifluoroacetylquinolines were elaborated to provide the corresponding compounds in high yields using a simple one-pot procedure. The possible mechanism of rearrangement is discussed.
- Muzalevskiy, Vasiliy M.,Belyaeva, Kseniya V.,Trofimov, Boris A.,Nenajdenko, Valentine G.
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p. 9993 - 10006
(2020/09/09)
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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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- Phosphine Ligand-Free Ruthenium Complexes as Efficient Catalysts for the Synthesis of Quinolines and Pyridines by Acceptorless Dehydrogenative Coupling Reactions
-
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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- Synthesis of 2-Arylisoindoline Derivatives Catalyzed by Reusable 1,2,4-Triazole Iridium on Mesoporous Silica through a Cascade Borrowing Hydrogen Strategy
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Covalent attachment of a 1,2,4-triazole iridium complex to mesoporous MCM-41 generated a heterogeneous catalyst that was found to be effective in the synthesis of 2-aryl isoindolines, quinolines, cyclic amines, and symmetrical secondary amines through a cascade borrowing hydrogen strategy. Interestingly, the supported heterogeneous iridium catalyst prepared from the 1,2,4-triazole iridium complex and mesoporous MCM-41 exhibited high catalytic activity in the preparation of 2-aryl isoindoline derivatives and symmetrical secondary amines. The catalyst system is highly recyclable for at least five times. Besides the important effect of the triazole, iridium sites grafted on siliceous supports can act as multifunctional catalytic centers and thus greatly enhance the catalytic activity of the catalysts. Furthermore, mechanistic experiments revealed that the reaction is initiated by an initial alcohol dehydrogenation and promoted by an iridium hydride intermediate. Importantly, the direct detection of a diagnostic iridium hydride signal confirmed that the synthesis of 2-aryl isoindolines occurs by a borrowing hydrogen process. This work provides an efficient example of isoindolines synthesis through a borrowing hydrogen strategy.
- Yao, Wei,Ge, Chenyang,Zhang, Yilin,Xia, Xiao-Feng,Wang, Long,Wang, Dawei
-
supporting information
p. 16099 - 16105
(2019/11/26)
-
- N-Heterocyclic carbene copper catalyzed quinoline synthesis from 2-aminobenzyl alcohols and ketones using DMSO as an oxidant at room temperature
-
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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- Dehydrogenative Synthesis of Quinolines, 2-Aminoquinolines, and Quinazolines Using Singlet Diradical Ni(II)-Catalysts
-
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)
-
- Metal-Ligand Cooperative Approach to Achieve Dehydrogenative Functionalization of Alcohols to Quinolines and Quinazolin-4(3 H)-ones under Mild Aerobic Conditions
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A simple metal-ligand cooperative approach for the dehydrogenative functionalization of alcohols to various substituted quinolines and quinazolin-4(3H)-ones under relatively mild reaction conditions (≤90 °C) is reported. Simple and easy-to-prepare air-stable Cu(II) complexes featuring redox-active azo-aromatic scaffolds, 2-arylazo-(1,10-phenanthroline) (L1,2), are used as catalyst. A wide variety of substituted quinolines and quinazolin-4(3H)-ones were synthesized in moderate to good isolated yields via dehydrogenative coupling reactions of various inexpensive and easily available starting materials under aerobic conditions. A few control experiments and deuterium labeling studies were carried out to understand the mechanism of the dehydrogenative coupling reactions, which indicate that both copper and the coordinated azo-aromatic ligand participate in a cooperative manner during the catalytic cycle.
- Das, Siuli,Sinha, Suman,Samanta, Deepannita,Mondal, Rakesh,Chakraborty, Gargi,Branda?, Paula,Paul, Nanda D.
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p. 10160 - 10171
(2019/08/20)
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- Intramolecular Desulfitative Coupling: Nickel-Catalyzed Transformation of Diaryl Sulfones into Biaryls via Extrusion of SO2
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As a new transformation of organosulfur compounds, intramolecular desulfitative coupling of diaryl sulfones to the corresponding biaryls has been developed with the aid of nickel-NHC catalysts. This catalytic elimination of SO2 was also applicable to alkenyl aryl sulfone to furnish the corresponding alkenyl arene.
- Takahashi, Fumiya,Nogi, Keisuke,Yorimitsu, Hideki
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p. 6601 - 6605
(2018/10/20)
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- π-Allylpalladium Species in Micelles of FI-750-M for Sustainable and General Suzuki-Miyaura Couplings of Unactivated Quinoline Systems in Water
-
General, clean, and sustainable Suzuki-Miyaura cross-couplings of 2-and 4-quinoline and isoquinoline systems have been demonstrated with use of π-allyl Pd catalyst in the nanomicelles of environmentally benign, proline-derived surfactant FI-750-M. Optimiz
- Handa, Sachin,Ibrahim, Faisal,Ansari, Tharique N.,Gallou, Fabrice
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p. 4229 - 4233
(2018/09/21)
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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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- Blue-light-promoted carbon-carbon double bond isomerization and its application in the syntheses of quinolines
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A blue-light-promoted carbon-carbon double bond isomerization in the absence of any photoredox catalyst is reported. It provides rapid access to a series of quinolines in good to excellent yields under simple aerobic conditions. The protocol is direct, catalyst-free and operationally convenient.
- Chen, Xinzheng,Qiu, Shuxian,Wang, Sasa,Wang, Huifei,Zhai, Hongbin
-
supporting information
p. 6349 - 6352
(2017/08/10)
-
- Development of a Unique Heterogeneous Palladium Catalyst for the Suzuki–Miyaura Reaction using (Hetero)aryl Chlorides and Chemoselective Hydrogenation
-
A unique heterogeneous palladium catalyst (7% Pd/WA30) supported on an anion exchange resin, which contains N,N-dimethylaminoalkyl functionalities on the polymer backbone, was developed. 7% Pd/WA30 could smoothly catalyze Suzuki–Miyaura reactions of even less reactive heteroaryl chlorides and heteroarylboronic acids to afford various (hetero)biaryls due to the electron-donating effect of the tert-amines on WA30 to Pd species. It was also applicable as a chemoselective hydrogenation catalyst, showing inactivity for the hydrogenolysis of tert-butyldimethylsilyl (TBS) ethers, alkyl benzyl ethers, and benzyl alcohols. The tert-amines on WA30 acted as moderate catalyst poisons for Pd, resulting in chemoselective hydrogenation. 7% Pd/WA30 was reused for at least five times without any loss of the hydrogenation catalytic activity. (Figure presented.).
- Ichikawa, Tomohiro,Netsu, Moeko,Mizuno, Masahiro,Mizusaki, Tomoteru,Takagi, Yukio,Sawama, Yoshinari,Monguchi, Yasunari,Sajiki, Hironao
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supporting information
p. 2269 - 2279
(2017/07/07)
-
- Synthesis of Quinolines via Iron-Catalyzed Redox Condensation of Alcohols with 2-Nitrobenzyl Methyl Ether/2-Nitrobenzyl Alcohols
-
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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p. 3985 - 3995
(2016/11/11)
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- Visible light-induced aerobic C-N bond activation: A photocatalytic strategy for the preparation of 2-arylpyridines and 2-arylquinolines
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An efficient method for accessing arylpyridines and arylquinolines via visible light-induced aerobic C-N bond activation is described. The applicability of different kinds of simple ketones, easily available amines, and the use of air as the sole oxidant make this transformation very attractive.
- Hu, Bei,Li, Yuyuan,Dong, Wuheng,Xie, Xiaomin,Wan, Jun,Zhang, Zhaoguo
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p. 48315 - 48318
(2016/06/09)
-
- ONO pincer type Pd(II) complexes: Synthesis, crystal structure and catalytic activity towards C-2 arylation of quinoline scaffolds
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Four new palladium(II) complexes featuring ONO pincer type hydrazone ligands were synthesized and characterized by spectroscopic and single-crystal XRD analysis. These complexes showed excellent catalytic activity towards the Suzuki-Miyaura cross coupling reaction of 2-chloroquinoline derivatives with various aryl boronic acids. The main advantages over previous methodologies include low catalyst loading, less problematic reaction media (H2O-DMF (80:20%)) and a lower reaction temperature of 60 °C for optimal performance.
- Arumugam, Vignesh,Kaminsky, Werner,Nallasamy, Dharmaraj
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p. 77948 - 77957
(2015/09/28)
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- Chiral phosphoric acid catalyzed oxidative kinetic resolution of cyclic secondary amine derivatives including tetrahydroquinolines by hydrogen transfer to imines
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A chiral Bronsted acid catalyzed dehydrogenative kinetic resolution of tetrahydroquinoline derivatives, which are representative of cyclic secondary amines, based on their hydrogen transfer to aromatic imines was efficiently achieved with high enantioselectivities. This hydrogen transfer of tetrahydroquinolines to imines was not driven by their aromatization to quinolines. This dehydrogenative kinetic resolution could be also applied to the asymmetric synthesis of various benzofused heterocycles containing secondary amine cores.
- Saito, Kodai,Miyashita, Hiromitsu,Akiyama, Takahiko
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supporting information
p. 16648 - 16651
(2015/11/25)
-
- TMEDA-assisted effective direct ortho arylation of electron-deficient N -heteroarenes with aromatic grignard reagents
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In the addition of TMEDA in toluene, aryl Grignards could effectively and site-specifically ortho-arylate electron-deficient heteroarenes under mild conditions. This endeavor successfully changed the old low-yielding reaction, aryl Grignard addition to N-heteroarenes, into an efficient procedure for heterobiaryls. The combination of the inexpensive aryl Grignards, TMEDA, the cost-free air, no use of any transition-metal catalyst, the mild reaction conditions, and the high-yielding gram-scale results enables this new procedure to be cost-effective and potentially utilizable in industry.
- Zhuo, Fang-Fang,Xie, Wen-Wen,Yang, Yong-Xin,Zhang, Lei,Wang, Pei,Yuan, Rui,Da, Chao-Shan
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p. 3243 - 3249
(2013/06/26)
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- Selective reduction of nitroarenes by a Hantzsch 1,4-dihydropyridine: A facile and efficient approach to substituted quinolines
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An efficient reductive cyclization of o-nitrocinnamoyl compounds was achieved by employing a Hantzsch 1,4-dihydropyridine ester as a biomimetic reducing agent in the presence of catalytic palladium on carbon. This approach was successfully applied to the synthesis of substituted quinolines. Georg Thieme Verlag Stuttgart ? New York.
- Xing, Rui-Guang,Li, Ya-Nan,Liu, Qiang,Han, Yi-Feng,Wei, Xia,Li, Jing,Zhou, Bo
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experimental part
p. 2066 - 2072
(2011/08/05)
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- Highly enantioselective hydrogenation of quinolines using phosphine-free chiral cationic Ruthenium catalysts: Scope, mechanism, and origin of enantioselectivity
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Asymmetric hydrogenation of quinolines catalyzed by chiral cationic η6-arene-N-tosylethylenediamine-Ru(II) complexes have been investigated. A wide range of quinoline derivatives, including 2-alkylquinolines, 2-arylquinolines, and 2-functionalized and 2,3-disubstituted quinoline derivatives, were efficiently hydrogenated to give 1,2,3,4-tetrahydroquinolines with up to >99% ee and full conversions. This catalytic protocol is applicable to the gram-scale synthesis of some biologically active tetrahydroquinolines, such as (-)-angustureine, and 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline, a key intermediate for the preparation of the antibacterial agent (S)-flumequine. The catalytic pathway of this reaction has been investigated in detail using a combination of stoichiometric reaction, intermediate characterization, and isotope labeling patterns. The evidence obtained from these experiments revealed that quinoline is reduced via an ionic and cascade reaction pathway, including 1,4-hydride addition, isomerization, and 1,2-hydride addition, and hydrogen addition undergoes a stepwise H+/H- transfer process outside the coordination sphere rather than a concerted mechanism. In addition, DFT calculations indicate that the enantioselectivity originates from the CH/π attraction between the η6-arene ligand in the Ru-complex and the fused phenyl ring of dihydroquinoline via a 10-membered ring transition state with the participation of TfO- anion.
- Wang, Tianli,Zhuo, Lian-Gang,Li, Zhiwei,Chen, Fei,Ding, Ziyuan,He, Yanmei,Fan, Qing-Hua,Xiang, Junfeng,Yu, Zhi-Xiang,Chan, Albert S. C.
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supporting information; experimental part
p. 9878 - 9891
(2011/08/10)
-
- Synthesis of quinolines by a solid acid-catalyzed microwave-assisted domino cyclization-aromatization approach
-
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)
-
- Base-mediated synthesis of quinolines: an unexpected cyclization reaction between 2-aminobenzylalcohol and ketones
-
Quinolines are prepared in an oxidative cyclization reaction between 2-aminobenzylalcohol and ketones. This reaction, that involves a hydrogen transfer, is mediated solely by a base without the need for a transition metal catalyst.
- Mierde, Hans Vander,Voort, Pascal Van Der,Verpoort, Francis
-
body text
p. 6893 - 6895
(2009/04/10)
-
- A ruthenium-catalyzed approach to the friedlaender quinoline synthesis
-
In a modification of the Friedlaender reaction, 2-aminobenzyl alcohol is oxidatively cyclized with a variety of ketones to yield substituted quinolines. Of all the ruthenium catalysts that were tested for this reaction, the second-generation Grubbs' catalyst gives the highest quinoline yield, in combination with KOtBu as a base. The presence of a hydrogen acceptor is required to regenerate the catalyst. Also the reaction mechanism is discussed, and the results show that there are possibly two different pathways towards quinolines. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Mierde, Hans Vander,Van Der Voort, Pascal,De Vos, Dirk,Verpoort, Francis
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scheme or table
p. 1625 - 1631
(2009/04/11)
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- A recyclable palladium-catalyzed modified Friedl?nder quinoline synthesis
-
2-Aminobenzyl alcohol reacts with an array of ketones in toluene/poly(ethylene glycol) (PEG-2000) at 100 °C in the presence of a palladium catalyst along with KOH under an atmosphere of air to give the corresponding quinolines in good yields. The catalytic system could be recovered and reused five times without any loss of catalytic activity.
- Cho, Chan Sik,Ren, Wen Xiu
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p. 4182 - 4186
(2008/02/10)
-
- Improved ruthenium catalysts for the modified Friedlaender quinoline synthesis
-
Herein we describe an improved ruthenium catalyst for the oxidative cyclization of 2-aminobenzylalcohol with ketones, leading to quinolines via a modified Friedlaender synthesis. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
- Vander Mierde, Hans,Ledoux, Nele,Allaert, Bart,Van Der Voort, Pascal,Drozdzak, Renata,De Vos, Dirk,Verpoort, Francis
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p. 1572 - 1574
(2008/03/13)
-
- Cobalt-catalyzed cross-coupling reactions of heterocyclic chlorides with arylmagnesium halides and of polyfunctionalized arylcopper reagents with aryl bromides, chlorides, fluorides and tosylates
-
A range of aromatic organocopper or organomagnesium compounds undergo smooth cross-coupling reactions with aryl bromides, chlorides, fluorides and tosylates, leading to polyfunctionalized aromatics or heterocycles in the presence of cobalt salts (5-7.5 mol%) as catalysts. Very mild reaction conditions are needed and, in the case of cross-coupling with organocopper compounds, Bu4NI (1 equiv) and 4-fluorostyrene (20 mol%) are essential as promoters for successful couplings. Georg Thieme Verlag Stuttgart.
- Korn, Tobias J.,Schade, Matthias A.,Cheemala, Murthy N.,Wirth, Stefan,Guevara, Simon A.,Cahiez, Gerard,Knochel, Paul
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p. 3547 - 3574
(2008/03/14)
-
- A copper(II)-catalyzed protocol for modified Friedl?nder quinoline synthesis
-
2-Aminobenzyl alcohol reacts with an array of ketones in dioxane at 100 °C in the presence of a catalytic amount of CuCl2 along with KOH under O2 atmosphere to afford the corresponding quinolines in good yields. 2-Aminobenzyl alcohol is also oxidatively coupled and cyclized with various aldehydes by step-by-step procedure, an initial treatment of 2-aminobenzyl alcohol in the presence of CuCl2 and KOH in dioxane under O2 atmosphere and subsequent addition of aldehyde to the mixture followed by stirring under argon atmosphere, to give 3-substituted quinolines in moderate to good yields.
- Cho, Chan Sik,Ren, Wen Xiu,Shim, Sang Chul
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p. 6781 - 6785
(2007/10/03)
-
- Palladium-catalyzed Sonogashira coupling reaction followed by isomerization and cyclization
-
2-Iodoaniline reacts with terminal acetylenic carbinols in THF at 80 °C in the presence of a catalytic amount of PdCl2(PPh3) 2 and CuI along with aqueous tetrabutylammonium hydroxide to afford the corresponding 2-arylquinolines in good yields. The catalytic pathway seems to be proceeded via a sequence involving initial Sonogashira coupling between 2-iodoaniline and terminal acetylenic carbinols to form coupled acetylenic carbinols, isomerization of coupled acetylenic carbinols to α,β- unsaturated ketones, and cyclodehydration.
- Cho, Chan Sik
-
p. 4094 - 4097
(2007/10/03)
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- Consecutive isomerization and cyclization of 3-(2-Aminophenyl)-1-arylprop- 2-yn-1-ols leading to 2-arylquinolines in the presence of potassium hydroxide
-
3-(2-Aminophenyl)-1-arylprop-2-yn-1-ols are readily converted to 2-arylquinolines in good yields in ethanol at 80° in the presence of potassium hydroxide via domino isomerization and cyclization.
- Cho, Chan Sik,Lee, Na Young,Kim, Tae-Jeong,Shim, Sang Chul
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p. 409 - 411
(2007/10/03)
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- New Cobalt-Catalyzed Cross-Coupling Reactions of Heterocyclic Chlorides with Aryl and Heteroaryl Magnesium Halides
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New cobalt-catalyzed cross-coupling between arylmagnesium halides and 2-chloropyridines and related heterocycles occur at low temperature leading to 2-arylated heterocycles in good yields.
- Korn, Tobias J.,Cahiez, Gérard,Knochel, Paul
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p. 1892 - 1894
(2007/10/03)
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- Imino-Diels-Alder and imino-aldol reactions catalyzed by samarium diiodide
-
In the presence of a catalytic amount of samarium diiodide in methylene chloride, aromatic imines react with Danishefsky diene to form tetrahydropyridine-4-ones in high yields. Under the same conditions, various imino-aldol reactions afford β-amino esters or β-amino ketones.
- Collin, Jacqueline,Jaber, Nada,Lannou, Marie Isabelle
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p. 7405 - 7407
(2007/10/03)
-
- Palladium-catalyzed heteroannulation with acetylenic carbinols as synthons-synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones
-
o-Iodoanilides 4 reacted with terminal acetylenic carbinols 5 under palladium-catalyzed conditions to yield o-substituted anilides 6. Most of the anilides 6 could be cyclized with NaOEt/EtOH to 2-arylquinolines 2. o-Iodoanilines 7 reacted with carbinols 5 leading to 8 which on palladium(II) assisted cyclisation afforded substituted quinolines 2. An excellent synthesis of the alkaloid dubamine (2n) is reported. Also, the anilides 6 on acid-catalyzed rearrangement, deprotection and cyclisation led to the 2-aryl-2, 3-dihydro-4(1H)-quinolones 16.
- Mahanty, Jyan S.,De, Mahuya,Das, Palas,Kundu, Nitya G.
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p. 13397 - 13418
(2007/10/03)
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- Synthesis of Quinolines and 2,3-Dihydro-4(1H)-quinolones. Palladium Catalysed Reaction of o-Iodoanilides with Acetylenic Carbinols
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A facile and general synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones was accomplished through palladium catalysed reaction of o-iodoanilides with acetylenic carbinols.Key Words: quinolines; 2,3-dihydro-4(1H)-quinolones; palladium catalysis; o-iodoanilines; acetylenic carbinols.
- Kundu, Nitya G.,Mahanty, Jyan S.,Das, Palas,Das, Biswajit
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p. 1625 - 1628
(2007/10/02)
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- A SIMPLE REGIOSELECTIVE PREPARATION OF 2- OR 3-SUBSTITUTED QUINOLINE DERIVATIVES VIA DIALKYLQUINOLYLBORANES
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Various quinoline derivatives possessing a substituent at the 2- or 3-position were prepared by the reaction of dialkylquinolylboranes and organic bromides in the presence of a palladium catalyst.
- Ishikura, Minoru,Oda, Izumi,Terashima, Masanao
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p. 2375 - 2386
(2007/10/02)
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