- 1H, 13C and 15N NMR and GIAO CPHF calculations on two quinoacridinium salts
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The complete 1H, 13C and 15N NMR assignments of two closely related quinoacridinium salts, 8,13-diethyl-6-methyl-8H-quino[4,3,2-kl]acridinium iodide and, 8,13-diethyl-3,6,11-trimethyl-8H-quino[4,3,2-kl]acridinium iodide, are described. The multinuclear 1D NMR and 2D shift-correlated NMR techniques HMQC, HSQC and HMBC were applied, accompanied by ab initia GIAO CPHF calculations of shielding constants. Copyright
- Jaroszewska-Manaj, Jolanta,Maciejewska, Dorota,Wawer, Iwona
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Read Online
- Oxidation of 1,2-dihydroquinolines under mild and heterogeneous conditions
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A combination of NaHSO4.H2O and Na2Cr2O7.2H2O in the presence of wet SiO2 were used as an effective oxidizing agent for the oxidation of 1,2-dihydroquinolines to their corresponding quinoline derivatives in dichloromethane at room temperature with excellent yields.
- Damavandi,Zolfigol,Karami
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Read Online
- Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents
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Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).
- An, Ju Hyeon,Kim, Kyu Dong,Lee, Jun Hee
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supporting information
p. 2876 - 2894
(2021/02/01)
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- Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies
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We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.
- Lecroq, William,Schleinitz, Jules,Billoue, Mallaury,Perfetto, Anna,Gaumont, Annie-Claude,Lalevée, Jacques,Ciofini, Ilaria,Grimaud, Laurence,Lakhdar, Sami
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p. 1237 - 1242
(2021/06/01)
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- ZnMe2-Mediated, Direct Alkylation of Electron-Deficient N-Heteroarenes with 1,1-Diborylalkanes: Scope and Mechanism
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The regioselective, direct alkylation of electron-deficient N-heteroarenes is, in principle, a powerful and efficient way of accessing alkylated N-heteroarenes that are important core structures of many biologically active compounds and pharmaceutical agents. Herein, we report a ZnMe2-promoted, direct C2- or C4-selective primary and secondary alkylation of pyridines and quinolines using 1,1-diborylalkanes as alkylation sources. While substituted pyridines and quinolines exclusively afford C2-alkylated products, simple pyridine delivers C4-alkylated pyridine with excellent regioselectivity. The reaction scope is remarkably broad, and a range of C2- or C4-alkylated electron-deficient N-heteroarenes are obtained in good yields. Experimental and computational mechanistic studies imply that ZnMe2 serves not only as an activator of 1,1-diborylalkanes to generate (α-borylalkyl)methylalkoxy zincate, which acts as a Lewis acid to bind to the nitrogen atom of the heterocycles and controls the regioselectivity, but also as an oxidant for rearomatizing the dihydro-N-heteroarene intermediates to release the product.
- Jo, Woohyun,Baek, Seung-Yeol,Hwang, Chiwon,Heo, Joon,Baik, Mu-Hyun,Cho, Seung Hwan
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supporting information
p. 13235 - 13245
(2020/09/01)
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- Method for producing quinoline derivative through one-pot two-step method
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The invention relates to a method for producing a quinoline derivative through a one-pot two-step method. According to the method, an aromatic nitro compound and fatty alcohol are used as raw materials, oxygen-containing molybdenum disulfide is used as a catalyst, firstly, under the conditions of 0.3-3.0-MPa hydrogen and 120-160 DEG C, a reaction is carried out for 2-10 h, the aromatic nitro compound is translated into an aromatic amine, then a reaction atmosphere is displaced, in an inert atmosphere or an oxygen-containing atmosphere, a reaction is carried out under the condition of 120-200 DEG C for 2-12 h, after the reaction is completed, a liquid-phase component is separated out, and is concentrated, and an obtained product is separated by a silica gel column to obtain a substituted qunoline compound. The synthesis method can have important application on the aspect of synthesis of quinoline compounds.
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Paragraph 0033-0036
(2020/02/17)
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- Method for preparing quinoline compound through oxidation and reduction integration (by machine translation)
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The method takes the aromatic nitro compound and the fatty alcohol as. the raw material and uses the aromatic nitro compound and the fatty, alcohol as the catalyst to, react under an inert atmosphere or under the, 150-200 °C atmosphere containing oxygen 2-12h, at the atmosphere, of oxygen containing, oxygen, to obtain the substituted, quinoline compound, and. the synthesis method can have important application in the aspect of quinoline compound. synthesis. (by machine translation)
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Paragraph 9-10
(2020/02/17)
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- Half-Sandwich Ruthenium Complexes for One-Pot Synthesis of Quinolines and Tetrahydroquinolines: Diverse Catalytic Activity in the Coupled Cyclization and Hydrogenation Process
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Four types of half-sandwich ruthenium complexes with an N,O-coordinate mode based on hydroxyindanone-imine ligands have been prepared in good yields. These stable ruthenium complexes exhibited high activity in the catalytic synthesis of quinolines from the reactions of amino alcohols with different types of ketones or secondary alcohols under very mild conditions. Moreover, the methodology for the direct one-pot synthesis of tetrahydroquinoline derivatives from amino alcohols and ketones has been also developed on the basis of the continuous catalytic activity of this ruthenium catalyst in the selective hydrogenation of the obtained quinoline derivatives with a low catalyst loading. The corresponding products, quinolines and tetrahydroquinoline derivatives, were afforded in good to excellent yields. The efficient and diverse catalytic activity of these ruthenium complexes suggested their potential large-scale application. All of the ruthenium complexes were characterized by various spectroscopies to confirm their structures.
- Yun, Xue-Jing,Zhu, Jing-Wei,Jin, Yan,Deng, Wei,Yao, Zi-Jian
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supporting information
p. 7841 - 7851
(2020/06/04)
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- Method for preparing quinoline derivative
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The invention relates to a method for preparing a quinoline derivative. The method comprises the following steps: by taking aromatic amine compounds and fatty alcohol as raw materials and oxygen-containing molybdenum disulfide as a catalyst, performing a reaction for 2-12 hours in an inert atmosphere or an oxygen-containing atmosphere at the temperature of 120-200 DEG C, after the reaction is finished, separating liquid phase components, performing concentration, and performing separation through a silica gel column, so as to obtain a substituted quinoline compound. The synthetic method may have important application in the aspect of quinoline compound synthesis.
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Paragraph 0037-0038
(2020/02/17)
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- Potassium tert-Butoxide-Promoted Acceptorless Dehydrogenation of N-Heterocycles
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Potassium tert-butoxide-promoted acceptorless dehydrogenation of N-heterocycles was efficiently realized for the generation of N-heteroarenes and hydrogen gas under transition-metal-free conditions. In the presence of KOtBu base, a variety of six- and five-membered N-heterocyclic compounds efficiently underwent acceptorless dehydrogenation to afford the corresponding N-heteroarenes and H2 gas in o-xylene at 140 °C. The present protocol provides a convenient route to aromatic nitrogen-containing compounds and H2 gas. (Figure presented.).
- Liu, Tingting,Wu, Kaikai,Wang, Liandi,Yu, Zhengkun
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supporting information
p. 3958 - 3964
(2019/08/01)
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- Discovery of fused heterocyclic carboxamide derivatives as novel α7-nAChR agonists: Synthesis, preliminary SAR and biological evaluation
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The α7 nicotinic acetylcholine receptor (α7 nAChR) has emerged as a promising therapeutic target for schizophrenia. In our previous work, a novel series of α7-nAChR agonists bearing scaffold of indolizine were discovered. To explore the effect of aromaticity on the activity and find more active agents, herein, fused heterocyclic carboxamide derivatives were designed and synthesized in this study. Based on the evaluation by two-electrode voltage clamp in Xenopus oocytes, 27 of the synthesized compounds showed obvious agonism of α7 nAChR. Particularly, compounds 10a and 10e showed significantly higher Emax than EVP-6124. The result illustrated the importance of aromaticity to the activity of agonism. Compound 10a, which showed EC50 of 1.88 μM and Emax of 72.4%, was further characterized comprehensively, including co-application with type II positive allosteric modulator PNU-120596, selectivity with other closely related ligand-gated ion channel, etc. The results showed that 10a showed moderate selectivity over other subtypes such as α4β2 and α3β4 nAChR. 10a evoked α7-like currents that were inhibited by MLA and enhanced in the presence of the α7 PAM PNU-120596. The analysis of binding mode and understanding of structure-activity relationship provided insights to develop more potent novel α7-nAChR agonists.
- Xue, Yu,He, Xiaomeng,Yang, Taoyi,Wang, Yuxi,Liu, Zhenming,Zhang, Guisen,Wang, Yanxing,Wang, Kewei,Zhang, Liangren,Zhang, Lihe
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- Photocatalytic tandem reaction of primary alcohols with arylamines in the synthesis of amides and alkylquinolines in the presence of a heterogeneous Fe(CrO2)2–TiO2/X system under aerobic conditions
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A heterogeneous system Fe(CrO2)2–TiO2/X (where X is promoter NiO, CuO, ZnO, Cr2O3, Fe2O3, PrOCl, TbOCl, LaOCl, or EuOCl) was prepared. The photocatalytic activity of the system was tested in the tandem reaction of primary alcohols (BnOH, EtOH) with arylamines aimed at synthesizing benzamides and substituted 2-methylquinolines under aerobic conditions at room temperature.
- Makhmutov
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- Deracemization of Phenyl-Substituted 2-Methyl-1,2,3,4-Tetrahydroquinolines by a Recombinant Monoamine Oxidase from Pseudomonas monteilii ZMU-T01
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A monoamine oxidase (MAO5) from Pseudomonas monteilii ZMU-T01 was first heterologously expressed in Escherichia coli BL21(DE3) and then used as a biocatalyst for the deracemization of racemic 2-methyl-1,2,3,4-tetrahdroquinoline derivatives to yield the unreacted R enantiomer with up to >99 % ee. Sequence alignment revealed that MAO5 shared 14.7 % identity toward the well-studied monoamine oxidase (MAO-N).
- Deng, Guozhong,Wan, Nanwei,Qin, Lei,Cui, Baodong,An, Miao,Han, Wenyong,Chen, Yongzheng
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p. 2374 - 2377
(2018/04/19)
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- Sequential Photoredox Catalysis for Cascade Aerobic Decarboxylative Povarov and Oxidative Dehydrogenation Reactions of N-Aryl α-Amino Acids
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A visible-light-driven sequential photoredox catalysis to allow N-aryl α-amino acids to experience efficient cascade aerobic decarboxylative Povarov and oxidative dehydrogenation (ODH) reactions is described. With a dicyanopyrazine-derived chromophore (DP
- Shao, Tianju,Yin, Yanli,Lee, Richmond,Zhao, Xiaowei,Chai, Guobi,Jiang, Zhiyong
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supporting information
p. 1754 - 1760
(2018/03/21)
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- Visible-Light Photocatalyzed Deoxygenation of N-Heterocyclic N-Oxides
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A scalable and operationally simple method is described that allows for the chemoselective deoxygenation of a wide range of N-heterocyclic N-oxides (a total of 36 examples). This visible-light-induced protocol features the use of only commercially available reagents, room-temperature conditions, and unprecedented chemoselective removal of the oxygen atom in a quinoline N-oxide in the presence of a pyridine N-oxide in the same molecule through the judicious selection of a photocatalyst.
- Kim, Kyu Dong,Lee, Jun Hee
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supporting information
p. 7712 - 7716
(2019/01/03)
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- Aerobic oxidative dehydrogenation of N-heterocycles catalyzed by cobalt porphyrin
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An efficient catalytic procedure has been developed for the aerobic oxidative dehydrogenation of N-heterocycles by cobalt porphyrin in the absence of any additives. The catalytic system could tolerate various 1,2,3,4-tetrahydroquinoline derivatives and some other N-heterocycles. The corresponding N-heteroaromatics could be obtained in 59–86% yields. The mechanism investigation suggested that the aerobic oxidative dehydrogenation might proceed with imine intermediate through radical paths.
- Zhou, Weiyou,Chen, Dongwei,Sun, Fu'an,Qian, Junfeng,He, Mingyang,Chen, Qun
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supporting information
p. 949 - 953
(2018/02/09)
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- Actinide-Based Porphyrinic MOF as a Dehydrogenation Catalyst
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Uranyl–organic frameworks (UOFs) have recently been the object of many research endeavors due to the unique coordination mode of uranyl ions and their attractive physicochemical properties. Here, a new (3,4)-connected UOF (U-IHEP-4) assembled from uranyl and porphyrin ligand tetrakis(4-carboxyphenyl)porphyrin (H4TCPP) is reported, which represents the first case of actinide porphyrinic MOFs. Adsorption experiments in DMF solution demonstrated that U-IHEP-4 selectively adsorbs positively charged dyes, which is in line with its negatively charged framework and large pore volume ratio (90 %). Remarkably, U-IHEP-4 exhibited high catalytic activity for the dehydrogenation of N-heterocycles to synthesize the corresponding aromatic heterocycles and it can be used as an efficient heterogeneous catalyst.
- Hu, Kong-Qiu,Huang, Zhi-Wei,Zhang, Zhi-Hui,Mei, Lei,Qian, Bing-Bing,Yu, Ji-Pan,Chai, Zhi-Fang,Shi, Wei-Qun
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supporting information
p. 16766 - 16769
(2018/10/31)
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- Fe(CrO2)2-catalyzed, photoactivated oxidative one-pot tandem synthesis of substituted quinolines from primary alcohols and arylamines
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[Figure not available: see fulltext.] A one-pot tandem synthesis of substituted quinolines involving selective catalytic oxidation of primary alcohols to the corresponding aldehydes and their subsequent condensation with arylamines has been developed. Fe(CrO2)2 has been used as a catalyst, and oxidation has been performed with aqueous H2O2. To accelerate the catalytic oxidation of alcohols, photoactivation method has been applied.
- Makhmutov, Aynur R.,Mustafin, Akhat G.,Usmanov, Salavat M.
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p. 369 - 374
(2018/05/28)
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- One-Pot Oxidative Synthesis of Substituted Quinolines from Alcohols and Arylamines Catalyzed by Fe(CrO2)2 in Water Medium
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One-pot tandem synthesis was developed for substituted quinolines (in up to 97% yields) involving a selective catalytic oxidation of primary amines to aldehydes and their condensation with arylamines under the action of a dispersion of Fe(CrO2)2 and water solution of H2O2 at room temperature. The stage of catalytic oxidation of alcohols was accelerated by photoactivation. A presumable mechanism of the photoactivated tandem synthesis of 2-methylquinoline was suggested. Catalyst Fe(CrO2)2 was prepared by photochemical synthesis.
- Makhmutov
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p. 1166 - 1172
(2018/10/24)
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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
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supporting information
p. 6349 - 6352
(2017/08/10)
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- H-phosphonate mediated sulfonylation of 2-substituted quinoline N-oxides: One-pot strategy for the synthesis of 3/4-sulfonylquinoline derivatives
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series of biologically important 3/4-sulfonylquinoline derivatives was synthesized starting from easily available sodium benzenesulfinates, diethyl H-phosphonate and 2-substituted quinoline N-oxides in onepot under metal-free conditions. H-phosphonate plays a decisive role in activating the C3-H, C4-H bonds of the 2-substituted quinoline N-oxides. The isolated 3/4-sulfonylquinolines were characterized by 1H, 13CNMR spectroscopy and HR MS.
- Ma, Huili,Liu, Shuyun,Zhu, Shaohua,Bi, Wenzhu,Chen, Xiaolan,Zhao, Yufen
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supporting information
p. 887 - 895
(2017/08/15)
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- Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines
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A unique, ruthenium-catalyzed, [3 + 3] annulation of anilines with allyl alcohols in the synthesis of substituted quinolines is reported. The method employs a traceless directing group strategy in the proximal C-H bond activation and represents a one-pot Domino synthesis of quinolines from anilines.
- Kumar, Gangam Srikanth,Kumar, Pravin,Kapur, Manmohan
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supporting information
p. 2494 - 2497
(2017/05/24)
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- Method for catalyzing nitrogen heterocyclic ring compound for oxidative dehydrogenation with hydrotalcite-like material
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The invention relates to a method for catalyzing a nitrogen heterocyclic ring compound for oxidative dehydrogenation with a hydrotalcite-like material, and belongs to the application aspect of a hydrotalcite-like component. The hydrotalcite-like component can be expressed as: A-MxM-LDHs (A=OH or CO3; M=Ni, Co, Cu, Mg or Zn; M=Fe, Mn, Al; M/M=(2 to 4)). Under existence of the catalyst and without adding any additives, oxidative dehydrogenation reaction is performed on the heterocyclic ring compound under a mild condition to prepare a corresponding aromatic compound. According to the method provided by the invention, the hydrotalcite-like material is based on non-noble metal, can be synthesized largely, and can be recycled; the method has the advantages of being high in catalytic reaction efficiency, mild in reaction condition, low in cost, easy to industrialize and the like.
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Paragraph 0048; 0049; 0050; 0051; 0052
(2017/10/27)
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- Palladium Nanoparticles Stabilized by Metal–Carbon Covalent Bonds as an Expeditious Catalyst for the Oxidative Dehydrogenation of Nitrogen Heterocycles
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The first method for the dehydrogenation of nitrogen heterocycles catalyzed by a palladium nanocatalyst was developed. Carbon–metal covalent-bond-stabilized nanoparticles were found to be efficient for the dehydrogenation process in the presence of tert-butyl hydroperoxide. A variety of N-heterocycles were transformed into functionalized quinolines in medium to excellent yields in water as the solvent under mild conditions by a simple operation.
- Sun, Xiao-Tao,Zhu, Jie,Xia, Yun-Tao,Wu, Lei
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p. 2463 - 2466
(2017/07/12)
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- Assembly of Diversely Substituted Quinolines via Aerobic Oxidative Aromatization from Simple Alcohols and Anilines
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An aerobic oxidative aromatization of simple aliphatic alcohols and anilines under the Pd(OAc)2/2,4,6-Collidine/Br?nsted acid catalytic system has been established, providing a direct approach for the preparation of diverse substituted quinoline derivatives in high yields with wide functional group tolerance. Practically, the protocol can be easily scaled up to gram-scale and was utilized in the concise formal synthesis of a promising herbicide candidate.
- Li, Jixing,Zhang, Jinlong,Yang, Huameng,Jiang, Gaoxi
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supporting information
p. 3284 - 3290
(2017/03/23)
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- Preparation method of quinoline derivative
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The invention provides a preparation method of a quinoline derivative. The method includes the steps of: in the presence of an oxidizing agent, adding a catalyst, then adding aniline or aromatic amine with different substituents, at the same time adding alcohol for reaction so as to prepare the quinoline derivative by one step. Specifically, the catalyst comprises a metal catalyst, an assistant catalyst I and an assistant catalyst II; the metal catalyst is a transition metal catalyst; the assistant catalyst I is an alkaline nitrogen-containing ligand; and the assistant catalyst II is an acidic compound. The quinoline derivative prepared by the method provided by the invention has stable performance and high purity. And the preparation method of the quinoline derivative can prepare quinoline, 2-methylquinoline, 8-hydroxyquinoline quinoline and other derivatives by one-step reaction, and the preparation method is simple and practicable. The preparation process does not produce new "three wastes", is environment-friendly, and provides a green and environment-friendly synthesis method. The preparation method has the characteristics of few raw material variety, little reaction equipment, few preparation step and low cost, and is more suitable for industrial production.
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Paragraph 0061; 0062
(2017/06/02)
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- Method for compounding quinoline compound in manner of oxidative dehydrogenation of tetrahydroquinoline compound through visible light catalysis
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The invention discloses a method for compounding a quinoline compound in the manner of oxidative dehydrogenation of a tetrahydroquinoline compound through visible light catalysis. The method comprises the following steps: utilizing oxygen to replace peroxide as an oxidizing agent; taking polysubstituted BODIPY organic compound as a photocatalyst; catalyzing the oxidative dehydrogenation of 1,2,3,4-tetrahydroquinoline compound and compounding the quinoline compound. Compared with the present compounding method, the method has the advantages of mild reaction condition, metal-free photocatalyst used in the reaction, less dosage of the catalyst, high catalytic efficiency, stabilization, high efficiency, simple operation, environmental protection, high conversion rate of products and excellent selectivity.
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Paragraph 0018; 0019; 0020-0023; 0030-0050; 0111-0114
(2017/10/07)
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- Synthesis of quinolines and naphthyridines: Via catalytic retro-aldol reaction of β-hydroxyketones with ortho -aminobenzaldehydes or nicotinaldehydes
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A Cu(i)-catalyzed retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes and nicotinaldehydes is reported that produces a range of quinolines and naphthyridines with high efficiency and selectivity. This reaction uses β-hydroxyketones as a regiospecific ketone-protected enolate source via copper-catalyzed retro-aldol Cα-Cβ bond cleavage. The in situ generated copper enolate undergoes kinetically favorable cyclization with ortho-amino aryl aldehydes to produce quinolines and naphthyridines in a chemo- and regioselective manner. The mild and weakly basic reaction conditions also suppress possible side reactions of benzaldehydes under strongly basic conditions, resulting in improved reaction yields.
- Zhang, Song-Lin,Deng, Zhu-Qin
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p. 8966 - 8970
(2016/10/05)
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- Quinolines synthesis by reacting 1,3-butanediol with anilines in the presence of iron catalysts
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2-, 4-, 6-, 7-, and 8-substituted quinolines were synthesized in 78–95% yield by the reaction of 1,3- butanediol with anilines in the presence of iron catalysts in carbon tetrachloride.
- Khusnutdinov,Bayguzina,Aminov
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p. 1613 - 1618
(2016/08/26)
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- Dual behavior of iodine species in condensation of anilines and vinyl ethers affording 2-methylquinolines
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A metal-free, mild and efficient method for the synthesis of 2-methylquinolines was successfully developed by condensation of anilines with vinyl ethers in the presence of catalytic amount of iodine. Modification of both pyridine and benzene moieties was easily achieved by changing only the vinyl ether and aniline. In this reaction, the iodine species was revealed to show dual behavior; molecular iodine serves as an oxidant, while its reduced form, hydrogen iodide, activates the vinyl ether. The redox reaction between these iodine species enables the use of a catalytic amount of iodine in this synthetic method.
- Le, Song Thi,Yasuoka, Chisa,Asahara, Haruyasu,Nishiwaki, Nagatoshi
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- Tris(pentafluorophenyl)borane-Catalyzed Acceptorless Dehydrogenation of N-Heterocycles
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Catalytic acceptorless dehydrogenation is an environmentally benign way to desaturate organic compounds. This process is traditionally accomplished with transition-metal-based catalysts. Herein, a borane-catalyzed, metal-free acceptorless dehydrogenation of saturated N-heterocycles is disclosed. Tris(pentafluorophenyl)borane was identified as a versatile catalyst, which afforded several synthetically important N-heteroarenes in up to quantitative yield. Specifically, the present metal-free catalytic system exhibited a uniquely high tolerance toward sulfur functionalities, and demonstrated superior reactivity in the synthesis of benzothiazoles compared to conventional metal-catalyzed systems. This protocol can thus be regarded as the first example of metal-free acceptorless dehydrogenation in synthetic organic chemistry.
- Kojima, Masahiro,Kanai, Motomu
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supporting information
p. 12224 - 12227
(2016/10/13)
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- A Convenient Procedure for the Oxidative Dehydrogenation of N-Heterocycles Catalyzed by FeCl2/DMSO
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A convenient catalytic procedure has been developed for the oxidative dehydrogenations of N-heterocycles. Combining catalytic FeCl2 with DMSO yields a catalyst that promotes the dehydrogenation of tetrahydroquinolines and related heterocycles under 1 bar of O2, affording the corresponding N-heteroaromatic products in moderate yields.
- Zhou, Weiyou,Taboonpong, Piyada,Aboo, Ahmed Hamdoon,Zhang, Lingjuan,Jiang, Jun,Xiao, Jianliang
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supporting information
p. 1806 - 1809
(2016/07/16)
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- Continuous Flow Doebner-Miller Reaction and Isolation Using Continuous Stirred Tank Reactors
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Continuous flow Doebner-Miller synthesis of different quinaldines from respective anilines is demonstrated using sulfuric acid as a homogeneous catalyst. The extent of reaction was monitored for various parameters, namely, temperature, residence time, mole ratio of sulfuric acid to substrate, mole ratio of crotonaldehyde to substrate, and so forth. Continuous stirred reactors in series were used as a preferred configuration for this rection that generates byproduct in the form of sticky solid material. The approach has been extended for six different anilines, and the results are compared with batch reactions. Continuous stirred reactors in series with distributed dosing of crotonaldehyde facilitated a continuous flow reaction with lower byproduct formation, increased yields, and continuous workup and is a scalable approach.
- Yadav, Maruti B.,Kulkarni, Sourabh,Joshi, Ramesh A.,Kulkarni, Amol A.
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supporting information
p. 1621 - 1625
(2016/09/23)
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- Quinoline Synthesis by the Reaction of Anilines with 1,2-diols Catalyzed by Iron Compounds
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The synthesis of quinoline derivatives by cyclocondensation of anilines with 1,2-ethanediol, 1,2-propanediol, and 1,2-butanediol in the presence of iron-containing catalysts was performed for the first time.
- Khusnutdinov, Ravil,Bayguzina, Alfiya,Aminov, Rishat,Dzhemilev, Usein
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supporting information
p. 1022 - 1029
(2016/07/28)
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- Nickel-catalyzed cross-coupling of anisole derivatives with trimethylaluminum through the cleavage of carbonoxygen bonds
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Nickel-catalyzed cross-coupling of methoxyarenes with trimethylaluminum is described. The use of 1,3-dicyclohexylimidazol-2-ylidene as a ligand and NaO'Bu as a base promotes the methylation of anisole derivatives via the cleavage of normally unreactive aryl carbonoxygen bonds.
- Morioka, Toshifumi,Nishizawa, Akihiro,Nakamura, Keisuke,Tobisu, Mamoru,Chatani, Naoto
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supporting information
p. 1729 - 1731
(2016/02/19)
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- Copper-Promoted Tandem Reaction of Azobenzenes with Allyl Bromides via N=N Bond Cleavage for the Regioselective Synthesis of Quinolines
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A copper-promoted tandem reaction of a variety of azobenzenes and allyl bromides via N=N bond cleavage to regioselectively construct quinoline derivatives has been developed. The azobenzenes act as not only construction units but also an oxidant for quinoline formation.
- Yi, Xiangli,Xi, Chanjuan
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supporting information
p. 5836 - 5839
(2015/12/11)
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- Copper-catalyzed oxygen atom transfer of N-oxides leading to a facile deoxygenation procedure applicable to both heterocyclic and amine N-oxides
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Deoxygenation of various types of N-oxides including both heterocyclic and alkyl(aryl)amine derivatives has successfully been developed by the copper-catalyzed oxygen atom transfer using diazo compounds as the oxygen acceptor. The reaction proceeds smoothly over a broad range of substrates with excellent functional group tolerance under mild conditions. This journal is
- Jeong, Jisu,Lee, Donggun,Chang, Sukbok
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supporting information
p. 7035 - 7038
(2015/04/22)
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- Magnetically separable palladium-graphene nanocomposite as heterogeneous catalyst for the synthesis of 2-alkylquinolines via one pot reaction of anilines with alkenyl ethers
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The present Letter describes the use of magnetically separable palladium-graphene nanocomposite, a complete magnetically separable catalyst for the synthesis of 2-alkyl quinolines via reaction of anilines with alkenyl ethers. Because of the uniform decoration of the Pd nanoparticles on support, the catalyst exhibited higher catalytic efficiency and it remains unaltered even after six repeated cycles.
- Verma, Sanny,Verma, Deepak,Jain, Suman L.
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p. 2406 - 2409
(2014/05/06)
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- Discovery and efficient synthesis of a biologically active alkaloid inspired by thiostrepton biosynthesis
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Thiostrepton, a natural peptide macrocycle, is of great interest due to its structural complexity and numerous biological activities, including anti-bacterial, anti-tumor, and anti-plasmodial activities. The quinaldic acid (QA) moiety-containing side ring (loop 2) was proven to play an important role in carrying out these functions. Previously, we proposed biosynthetic logic for thiostrepton loop 2 and demonstrated the formation mechanism of QA. Herein, we report the discovery and efficient synthesis of a biologically active alkaloid, that is, a key intermediate involved in the thiostrepton biosynthetic pathway. A chemo-enzymatic method was performed to synthesize the molecule, and a series of analogs were prepared for bioassays, which included the examination of anti-bacterial and anti-tumor activities.
- Zheng, Qingfei,Wang, Shoufeng,Liu, Wen
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p. 7686 - 7690
(2014/12/10)
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- Acceptorless dehydrogenation of nitrogen heterocycles with a versatile iridium catalyst
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Gas up: A cyclometalated iridium complex is found to catalyze the dehydrogenation of various benzofused N-heterocycles, thus releasing H 2. Driven by as low as 0.1 mol % catalyst, the reaction affords quinolines, indoles, quinoxalines, isoquinolines, and β-carbolines in high yields. Copyright
- Wu, Jianjun,Talwar, Dinesh,Johnston, Steven,Yan, Ming,Xiao, Jianliang
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supporting information
p. 6983 - 6987
(2013/07/26)
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- High throughput one pot synthesis of 2-methylquinolines
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Various 2-methylquinolines have been successfully synthesized by using anilines and ethyl vinyl ether in 1:3 mole ratios in the presence of acetic acid. Stirring at rt for 3-4 h followed by reflux for 3.5-4 h resulted in the corresponding 2-methylquinolines in good yield. Copyright
- Chandrashekarappa, Kiran Kumar H.,Mahadevan, Kittappa M.,Manjappa, Kiran B.
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p. 1368 - 1370
(2013/04/23)
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- Synthesis of substituted quinolines by the reaction of anilines with alcohols and CCl4 in the presence of Fe-containing catalysts
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Substituted quinolines were synthesized by the reaction of aniline derivatives with aliphatic alcohols and CCl4 upon the action of the FeCl3·6H2O catalyst.
- Khusnutdinov,Bayguzina,Aminov
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p. 133 - 137
(2013/11/19)
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- Facile synthesis of 2-methylquinolines from anilines on mesoporous N-doped TiO2 under UV and visible light
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Nitrogen-doped TiO2 was synthesized by a simple wet method using a nitrogen precursor hydrazine hydrate and nano TiO2. This photocatalyst was characterized by X-ray diffraction, highresolution transmission electron microscopy, diffused reflectance spectra, photoluminescence, and X-ray photoelectron spectroscopy. XPS analysis indicates the incorporation of anionic nitrogen in TiO2 lattice as O-Ti-N linkage. N2 adsorption-desorpion isotherm indicates the mesoporous nature of N-TiO2 with the surface area 130.0 m2/g. Sizes of N-TiO2 particles are found to be in the range of 5-30 nm by HRTEM images. DRS spectra reveal the extended absorption to the visible range. N-TiO2 is found to be more efficient than Ag-TiO2, Au-TiO2, and Pt-TiO2 in quinaldine synthesis under visible light. Copyright Taylor & Francis Group, LLC.
- Selvam,Swaminathan
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p. 500 - 508
(2013/05/21)
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- Nano Pt-TiO2 for an efficient one-pot photocatalytic synthesis of quinaldines from anilines and ethanol
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Nanosized platinum particles loaded on the TiO2 nanoparticles were prepared to assess its photocatalytic activity in simple one-pot synthesis of quinaldines from anilines in ethanol using UV light. The catalyst was characterized by X-ray diffra
- Selvam, Kaliyamoorthy,Sreedhar, Bojja,Swaminathan, Meenakshisundaram
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experimental part
p. 761 - 773
(2012/08/07)
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- One-pot photocatalytic synthesis of quinaldines from nitroarenes with Au loaded TiO2 nanoparticles
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One-pot photocatalytic synthesis of quinaldines from nitroarenes using Au-TiO2 nanoparticles is reported. Au-TiO2 on irradiation induces a combined redox reaction with nitroarene and alcohol and the products undergo condensation-cyclization process to give quinaldines.
- Selvam,Swaminathan
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scheme or table
p. 389 - 393
(2011/12/15)
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- Novel redox photocatalyst Pt-TiO2 for the synthesis of 2-Methylquinolines from nitroarenes
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An eco-friendly and efficient procedure for synthesis of 2-methylquinoline derivatives from nitroarenes has been developed by a simple one-pot reaction on the surface of platinum-loaded TiO2 with neat ethanol under UV irradiation without any harsh reagent according to green chemistry. TiO 2 catalysts with various amounts of Pt loadings were prepared by photodeposition using chloroplatinic acid solution and characterized by XRD, BET, AFM, HR-TEM, XPS, and DRS. XRD patterns showed that the crystal structure of Pt-TiO2 still remained as anatase phase. The UV-vis spectra indicated that Pt promoted the absorption of visible light. The XPS measurements reveal that platinum particles are present mainly in metallic form. AFM and HR-TEM analysis revealed the presence of nonspherical shaped platinum nanoparticles of the diameter 312 nm. Pt-TiO2 on irradiation induces a combined redox reaction with nitroarene and alcohol and this is followed by condensationcyclization of aniline and oxidation products to give 2-methylquinolines
- Selvam, Kaliyamoorthy,Swaminathan, Meenakshisundaram
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experimental part
p. 953 - 959
(2011/10/18)
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- Assembly of substituted 2-alkylquinolines by a sequential palladium-catalyzed Ci-N and Ci-C bond formation
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Diversity: A range of substituted 2-alkylquinolines can be prepared in a general and efficient synthetic approach that employs mild reaction conditions (see scheme). The synthesis is based on a sequential palladium-catalyzed Ci-N and Ci-C bond formation, followed by palladium-catalyzed aromatization, and results in the formation of the desired compounds in one step. Copyright
- Matsubara, Yoshio,Hirakawa, Saori,Yamaguchi, Yoshihiro,Yoshida, Zen-Ichi
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experimental part
p. 7670 - 7673
(2011/10/05)
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- A catalyst-free benzylic C-H bond olefination of azaarenes for direct mannich-like reactions
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A highly efficient synthesis of trans-alkenylazaarene under catalyst-free conditions was developed via the addition of methylazaarenes to N-sulfonyl aldimines and a subsequent C-N elimination in situ. A one-pot procedure for this addition-elimination was also developed. The reaction could tolerate a broad substrate scope and give the corresponding alkenylazaarenes in high yields.
- Yan, Yizhe,Xu, Kun,Fang, Yang,Wang, Zhiyong
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experimental part
p. 6849 - 6855
(2011/10/04)
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- One-pot synthesis of quinoline derivatives directly from terminal alkynes via sequential ruthenium(II) and acid catalysis
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A convenient one-pot synthesis of 2,3-di- substituted, 2,3,6- trisubstituted, and 2,3,6,7-tetrasubstituted quinoline analogues from terminal alkynes via sequential ruthenium(II) and para-toluenesulfonic acid (p-TSA) co-catalyzed reactions is described. The catalytic process is shown to take place first via intermediate formation of an allyl ketone and then addition of an aniline derivative to the allyl ketone. The p-TSA is a catalyst for both allyl ketone and quinoline synthetic steps. The method allowed us to synthesize a wide range of quinoline derivatives and introduce different substituents by employing various simple starting materials. The reaction allows the synthesis of halogen-containing products.
- Zhang, Min,Roisnel, Thierry,Dixneufc, Pierre H.
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body text
p. 1896 - 1903
(2010/11/05)
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- Au-doped TiO2 nanoparticles for selective photocatalytic synthesis of quinaldines from anilines in ethanol
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A convenient eco-friendly photocatalytic synthesis of quinaldines has been developed by a simple one-pot reaction of anilines in ethanol solution with Au-loaded TiO2 under UV irradiation. Upon irradiation in the presence of Au-TiO2, aniline and oxidation products derived from ethanol undergo condensation-cyclization to afford quinaldines.
- Selvam,Swaminathan
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scheme or table
p. 4911 - 4914
(2010/10/02)
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- Miceller-mediated phosphomolybdic acid: Highly effective reusable catalyst for synthesis of quinoline and its derivatives
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A simple, efficient, and ecofriendly procedure has been developed for the synthesis of quinoline and its derivatives in a one-pot reaction of aniline with crotonaldehyde or methyl vinyl ketone using phosphomolybdic acid as solid acid catalyst in miceller media. The catalyst was easily recycled and reused. Copyrigh
- Chaskar, Atul,Padalkar, Vikas,Phatangare, Kiran,Langi, Bhushan,Shah, Chetan
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experimental part
p. 2336 - 2340
(2010/09/10)
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- Multifunctional catalysis of heteropoly acid: One-pot synthesis of quinolines from nitroarene and various aldehydes in the presence of hydrazine
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12-Molybdophosphoric acid catalyzed transfer hydrogenation of nitroarene by hydrazine in a homogeneous phase. This catalytic system was applicable to one-pot quinolines synthesis in the presence of various aldehydes in water. This method provides a new and efficient protocol in terms of mild reaction conditions, clean reaction profiles, small quantity of catalyst, and simple work-up procedure.
- Hekmatshoar, Rahim,Sajadi, Sodeh,Sadjadi, Samaheh,Heravi, Majid M.,Beheshtiha, Yahya S.,Bamoharram, Fatemeh F.
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experimental part
p. 1195 - 1198
(2009/12/03)
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