- Efficient synthesis of tetrahydroquinolines from the reaction of aldehyde, aniline, and alkene under the in situ redox of SnCl2 and FeCl 3
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A highly efficient three-component Povarov reaction for the synthesis of tetrahydroquinoline derivatives was reported. The reaction of aldehyde, aniline, and alkene was carried out in the presence of Sn(IV), which was generated in situ from the redox reaction of SnCl2 and FeCl3, to afford tetrahydroquinoline derivatives in good to excellent yields. This discovery showed a sharp difference from the direct use of unstable SnCl4. Both aliphatic and aromatic aldehydes could be applied for the synthesis of the heterocycle in the reaction. The structure of the product 6-chloro-4-methyl-4- neopentyl-2-propyltetrahydroquinoline and 6-bromo-4-methyl-4-neopentyl-2- propyltetrahydroquinoline was confirmed by X-ray diffraction analysis.
- Guo, Qiaoxia,Teng, Weiling,Ren, Shenyong,Rao, Shasha,Wang, Yanqing,Chen, Liwei,Shen, Baojian,Takahashi, Tamotsu
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- THE TRANSITION METAL-CATALYZED N-ALKYLATION AND N-HETEROCYCLIZATION. A REDUCTIVE TRANSFORMATION OF NITROBENZENE INTO N,N-DIALKYLANILINE AND 2,3-SUBSTITUTED QUINOLINE USING ALDEHYDE AND CARBON MONOXIDE
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The catalytic N-alkylation and N-heterocyclization of nitrobenzene occurs at 180 deg C under pressures of carbon monoxide (70 atm) in the presence of aldehyde and transition metal complexes to give 2,3-dialkyl quinoline and N,N-dialkylaniline in good yields.The product selectivity highly depends on the catalysts.
- Watanabe, Yoshihisa,Suzuki, Naoki,Shim, Sang Chul,Yamamoto, Michihiro,Mitsudo, Take-aki,Takegami, Yoshinobu
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Read Online
- 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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Read Online
- Ruthenium-catalyzed formal alkyl group transfer: Synthesis of quinolines from nitroarenes and alkylammonium halides
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Nitroarenes are reductively cyclized with an array of tetraalkylammonium halides and trialkylammonium chlorides in the presence of a catalytic amount of a ruthenium catalyst along with tin(II) chloride dihydrate at 180° to afford the corresponding quinolines in moderate to good yields. The addition of tin(lI) chloride dihydrate is necessary for the effective formation of quinolines and toluene is the solvent of choice. A reaction pathway involving initial reduction of nitroarenes to anilines and conversion of alkylammonium halides to alkylamines, alkyl group transfer from alkylamines to anilines to form an imine, dimerization of imine, and heteroannulation is proposed for this catalytic process.
- Cho, Chan Sik,Lee, Na Young,Kim, Tae-Jeong,Shim, Sang Chul
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Read Online
- On the mechanism of the chemiluminescent condensation of aniline with butyraldehyde catalyzed by LnCl3 ? 6H2O
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The mechanism of the chemiluminescent condensation of aniline with butyraldehyde into 3-ethyl-2-propylquinoline catalyzed by LnCl3 ? 6H2O (Ln = Tb, Ho) is reported. A likely scheme of the catalytic condensation of aniline with butyraldehyde has been developed by simulation of separate steps of the reaction using chemiluminescence and photoluminescence methods and quantum-chemical calculations of the heats of these steps.
- Bulgakov,Kuleshov,Makhmutov,Dzhemilev
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Read Online
- 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 0047-0048
(2020/02/17)
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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 0043-0044
(2020/02/17)
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- Reaction behaviour of arylamines with nitroalkenes in the presence of bismuth(iii) triflate: An easy access to 2,3-dialkylquinolines
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We report the reaction behaviour of arylamines with nitroalkenes in the presence of bismuth(iii) triflate (10 mol%) and diacetoxyiodobenzene (10 mol%). We obtained 2,3-dialkylquinoline derivatives instead of the expected 3-alkylindole derivatives. The present reaction is an alternative approach for the synthesis of 2,3-dialkylquinoline derivatives under milder conditions. Furthermore, we establish the mechanistic pathway by theoretical calculations using Gaussian 09 software [B3LYP/6-311+G(d,p)], which shows that the conventional aza-Michael reaction is preferred over Michael addition. Aliphatic nitroalkenes behave in a different manner than aromatic nitroalkenes. An aza-Michael adduct gives rise to an imine by the elimination of water which may tautomerize to the corresponding enamine. The resulting imine and enamine intermediates react together to afford the desired quinoline derivatives. This protocol has the advantages of consecutive formation of one C-N and two C-C bonds, high regioselectivity, broad substrate-scope and good yields.
- Ali, Saghir,Gattu, Radhakrishna,Singh, Varun,Mondal, Santa,Khan, Abu T.,Dubey, Gurudutt,Bharatam
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p. 1785 - 1793
(2020/03/17)
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- Mesoporous Aluminosilicates in the Synthesis of N-Heterocyclic Compounds
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Abstract: The catalytic properties of samples of amorphous mesoporous aluminosilicate ASM with different Si/Al molar ratios (40, 80, 160) were studied in the synthesis of practically important pyridines (by the interaction of С2–С5 alcohols with formaldehyde and ammonia, cyclocondensation of acetaldehyde and propionic aldehyde with ammonia), dialkylquinolines and alkyltetrahydroquinolines (by reaction of aniline with C3, C4 aldehydes) and alkyldihydroquinolines (by interaction of aniline with ketones, acetone and acetophenone). It is found that mesoporous aluminosilicate ASM sample with a molar ratio of Si/Al = 40, which has the highest acidity among the studied samples, exhibits the highest activity and selectivity in these reactions.
- Agliullin, M. R.,Bikbaeva, V. R.,Bubennov, S. V.,Filippova, N. A.,Gataulin, A. R.,Grigor’eva, N. G.,Kostyleva, S. A.,Kutepov, B. I.,Narender, Nama
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p. 733 - 743
(2020/02/25)
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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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- Single-Pot Synthesis of Alkyl-Substituted Quinolines and Indoles via Photoinduced Oxidation of Primary Alcohols
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Single-pot synthesis of alkyl-substituted quinolines and indoles has been performed via photoinduced oxidation of primary aliphatic alcohols (C2–C5) and condensation of the aldehydes (products of the alcohols oxidation) with aniline under the action of iron-containing catalysts and inorganic oxidants. The synthesis was the most efficient in the presence of FeCl3·6H2O as catalyst and 10% aqueous solution of NaOCl as oxidant with irradiation by Hg lamp. The synthesis mechanism through photoinduced oxidation of primary aliphatic alcohol has been suggested.
- Makhmutov
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p. 892 - 897
(2018/07/06)
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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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- Heterogeneous catalytic synthesis of quinoline compounds from aniline and C1-C4 alcohols over zeolite-based catalysts
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The synthesis of quinolines from aniline and a C1-C4 alcohol was conducted under gas-phase reaction conditions over a series of zeolite-based catalysts. The texture and acid properties of catalysts were characterized by XRD, FT-IR, BET and NH3-TPD techniques. It was found that the total yield of quinolines was positively related to the relative content of Lewis acid sites of the catalyst. Among others, the ZnCl2/Ni-USY-acid catalyst possessed the best performance. Over this catalyst, the reactions of aniline and most of the alcohols provided a 42.3-79.7% total yield of quinolones under mild conditions, however, those of aniline and methanol, ethanol and iso-propanol predominantly led to N-alkylanilines. Furthermore, the reaction pathways for synthesizing quinolines via aniline reacting with polyhydric alcohols or monohydric alcohols was proposed in our work.
- Huang, Chen,Li, An,Chao, Zi-Sheng
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p. 48275 - 48285
(2017/10/31)
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- Synthesis of quinoline derivatives from anilines and aldehydes catalyzed by Cp2ZrCl2 and recyclable Cp2ZrCl2/MCM-41 system
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A facile method for the synthesis of quinoline derivatives using catalytic amount of Cp2ZrCl2 or Cp2ZrCl2 supported on MCM-41 (Cp2ZrCl2/MCM-41) in reaction of anilines and aldehydes is described. When Cp2ZrCl2/MCM-41 was used as catalyst, the yields of quinolines were enhanced by 5-15% compared with Cp2ZrCl2 as catalyst alone under the same reaction conditions. More importantly, Cp2ZrCl2/MCM-41 catalyst can be reused at least thrice by simple recover via filtration in air. Moreover, both Cp2ZrCl2 and Cp2ZrCl2/MCM-41 showed good catalytic activities to generate corresponding quinoline derivatives in moderate to good yields by varying the substituent of aniline and aldehyde. And the reaction conditions were optimized by studying the influences of reactant ratio, additives, solvent effect and reaction temperatures.
- Guo, Qiaoxia,Liao, Lijun,Teng, Weiling,Ren, Shenyong,Wang, Xiao,Lin, Yingying,Meng, Fanfang
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p. 117 - 122
(2016/02/03)
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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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- Rhodium-catalyzed synthesis of quinolines and imines under mild conditions
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An environmentally benign protocol for the synthesis of quinolines in aqueous medium by using a Rh(ii)acetate/TPPTS recyclable catalytic system has been developed. Anilines reacted smoothly with allyl alcohols furnishing the corresponding quinolines in moderate to good yields. This catalytic system was recycled up to five runs without much loss in its catalytic activity. Furthermore, imines were also synthesized from benzylamines in moderate to good yields.
- Yadav, Dilip Kumar T.,Bhanage, Bhalchandra M.
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p. 51570 - 51575
(2015/06/25)
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- Synthesis of 2,3-disubstituted quinolines from in situ generated imines and its enamine tautomer under radical cation induced conditions
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A tandem cyclization/aromatization of anilines and aldehydes was achieved under catalytic radical cation salt induced conditions, producing a series of 2,3-disubstituted quinolines in good yields. In this reaction, the in situ generated imine tautomerizes to enamine, which acts as a dienophile to participate in the tandem cyclization, and further elimination of the anilino group triggers the aromatization of tetrahydroquinolines, avoiding harsh conditions.
- Jia, Xiaodong,Peng, Fangfang,Qing, Chang,Huo, Congde,Wang, Yaxin,Wang, Xicun
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supporting information
p. 4950 - 4952
(2013/08/28)
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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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- Alkylation of aniline with methanol in the presence of FeCl 3·6H2O in carbon tetrachloride
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The reaction of aniline with methanol in the presence of FeCl 3·6 H2O in carbon tetrachloride leads to the formation of N-methyl- and N,N-dimethylanilines and 4,4′-methylenebis(N,N- dimethylaniline).
- Khusnutdinov,Bayguzina,Aminov
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p. 1447 - 1450
(2014/01/06)
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- Aerobic oxidative coupling of alcohols and amines over Au-Pd/resin in water: Au/Pd molar ratios switch the reaction pathways to amides or imines
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A facile switch of the reaction pathways of aerobic oxidative coupling of alcohols and amines from amidation to imination was realized for the first time by tuning the Au/Pd ratios in ion-exchange resin supported Au-Pd alloy catalysts (Au-Pd/resin). Amides were obtained with high yields on Au6Pd/resin while imines were obtained over AuPd4/resin. Various alcohols and amines underwent oxidative coupling smoothly in water to afford the desired products with good to excellent yields. Further investigation on the reaction mechanism suggested the synergistic effect between Au and Pd determined the adsorption strength of the aldehyde intermediate, which in turn dictated the reaction pathways. That is, on Au-rich alloys (e.g., Au6Pd) absorbed aldehyde species was formed, followed by further oxidation to yield amides, while on Pd-rich alloys (e.g., AuPd4), free aldehyde was generated, which then underwent condensation with amines to produce imines. The discovery might provide avenues to develop new efficient catalysts for the green synthesis of special chemicals.
- Zhang, Leilei,Wang, Wentao,Wang, Aiqin,Cui, Yitao,Yang, Xiaofeng,Huang, Yanqiang,Liu, Xiaoyan,Liu, Wengang,Son, Jin-Young,Oji, Hiroshi,Zhang, Tao
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supporting information
p. 2680 - 2684
(2013/10/08)
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- Oxidant effect of H2O2 for the syntheses of quinoline derivatives via one-pot reaction of aniline and aldehyde
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(Chemical Equation Presented) A convenient one-pot method for the synthesis of substituted quinolines via the reaction of aniline and aldehyde in the presence of a Lewis acid (AlCl3) and an oxidant (H2O 2) has been developed. Hydrogen peroxide was found to promote the reaction by its function as a hydrogen hunter, hindering the formation of by-product N-alkylaniline. The effect of the oxidant on the yield and selectivity was studied. When the molar ratio of aniline, n-butyraldehyde, and H2O2 was 1:3:0.5 at 25°C, the yield of 3-ethyl-2-propylquinoline was improved from 64% (reaction without H 2O2) to 84% (with H2O2), and the quinoline selectivity was improved to almost 100%. Moreover, the reaction time was obviously reduced. The substituent effect was also investigated in this work. Copyright Taylor & Francis Group, LLC.
- Guo, Qiaoxia,Wang, Wennian,Teng, Weiling,Chen, Liwei,Wang, Yanqing,Shen, Baojian
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experimental part
p. 2574 - 2584
(2012/07/14)
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- Synthesis of N-alkylanilines and substituted quinolines by reaction of aniline with alcohols and CCl4 effected with Ni-containing catalysts
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Syntheses of N-alkylanilines and 2,3-disubstituted quinolines by the reaction of aniline with CCl4 and aliphatic alcohols under the action of nickel-containing catalysts, in particular, Ni(OAc)2· 4H2O-Et3N.
- Khusnutdinov,Baygusina,Aminov,Dzhemilev
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experimental part
p. 690 - 693
(2012/10/08)
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- Titania-supported iridium subnanoclusters as an efficient heterogeneous catalyst for direct synthesis of quinolines from nitroarenes and aliphatic alcohols
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A versatile heterogeneous catalyst consisting of sub-nanosized iridium clusters deposited on titania (Ir/TiO2-NCs) promotes the direct tandem synthesis of quinoline derivatives from readily available nitroarenes and aliphatic alcohols under mild and additive-free conditions (see scheme). The process tolerates the presence of various reactive functional groups and is highly selective.
- He, Lin,Wang, Jian-Qiang,Gong, Ya,Liu, Yong-Mei,Cao, Yong,He, He-Yong,Fan, Kang-Nian
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supporting information; experimental part
p. 10216 - 10220
(2011/11/13)
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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)
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- One-pot friedlnder quinoline synthesis: Scope and limitations
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A highly effective one-pot Friedlnder quinoline synthesis from o-nitroarylcarbaldehydes and ketones or aldehydes was developed and the scope and limitations of the method were examined. The o-nitroarylcarbaldehydes were reduced to o-aminoarylcarbaldehydes with iron in the presence of a catalytic amount of aqueous hydrochloric acid; the amino compounds were then condensed in situ with ketones or aldehydes to form mono- or disubstituted quinolines, respectively, in good-to-excellent yields (58-100%). Georg Thieme Verlag Stuttgart - New York.
- Li, An-Hu,Beard, David J.,Coate, Heather,Honda, Ayako,Kadalbajoo, Mridula,Kleinberg, Andrew,Laufer, Radoslaw,Mulvihill, Kristen M.,Nigro, Anthony,Rastogi, Pawan,Sherman, Dan,Siu, Kam W.,Steinig, Arno G.,Wang, Ti,Werner, Doug,Crew, Andrew P.,Mulvihill, Mark J.
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experimental part
p. 1678 - 1686
(2010/06/22)
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- Synthesis of substituted quinolines from arylamines and aldehydes via tandem reaction promoted by chlorotrimethylsilane
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Substituted quinolines were effectively synthesised by utilising chlorotrimethylsilane (TMSCI) as an efficient catalyst in the cyclisation condensation of aromatic amines and enolisable aldehydes via a tandem process in air and DMSO. The clean, mild reaction conditions, operational simplicity and high yields were attractive features of the reaction which enables a facile preparative procedure for building the quinoline ring.
- Bian, Xiaoqin,Liu, Lanhai,Geng, Xin,Xie, Zengyang,Li, Shuangshuang,Wang, Cunde
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experimental part
p. 81 - 83
(2009/11/30)
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- Lanthanide(III) ion as a luminescent and catalytically active reaction center of aniline condensation with butyraldehyde
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A new type of chemiluminescence catalytic conversion in which the lanthanide(III) ion is a luminescent and highly efficient catalytically active center was found. Chemiluminescence (CL) is generated in the condensation reaction of aniline with butyraldehyde in DMF to form 3-ethyl-2-propylquinoline. The reaction is catalyzed by LnCl3?6H2O (Ln = Eu, Tb, and Ho). When EuCl3?6H2O and TbCl 3?6H2O salts are used as catalysts, the CL emitters are the Eu3+*and Tb3+*excited ions. In the case of HoCl3?6H2O, the emitter is 3-ethyl-2-propylquinoline in the triplet-excited state.
- Bulgakov,Kuleschov,Makhmutov
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p. 443 - 445
(2008/03/28)
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- Facile three-component synthesis of substituted quinolines catalyzed by iridium(III) complex
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A convenient and efficient synthesis of substituted quinolines via a simple one-pot reaction of an aniline, an aromatic aldehyde, and an enolizable aliphatic aldehyde in the presence of the iridium catalyst [IrCl 2H(cod)]2 under oxygen as an oxidant was developed. The reaction proceeds with Mannich-type imine formation followed by nucleophilic addition to give β-amino aldehydes. Dehydrative cyclization takes place to give dihydroquinoline, which is then dehydrogenated by aerobic oxidation to give 2-aryl-3-alkylquinolines. Dialkylquinolines were obtained by the reaction with anilines and aliphatic aldehydes in good yields.
- Nakajima, Takayuki,Inada, Takashi,Igarashi, Takeyuki,Sekioka, Tadashi,Shimizu, Isao
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p. 1941 - 1949
(2007/10/03)
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- Practical and simple synthesis of substituted quinolines by an HCL-DMSO system on a large scale: Remarkable effect of the chloride ion
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A variety of substituted quinolines are synthesized from imines and enolizable carbonyl compounds under aerobic conditions, in which only water is a byproduct. In DMSO, a catalytic amount of HCl activates carbonyl compounds quite effectively to give the quinolines. A simple and practical procedure is demonstrated on a large scale.
- Tanaka, Shin-Ya,Yasuda, Makoto,Baba, Akio
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p. 800 - 803
(2007/10/03)
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- One-pot synthesis of substituted quinolines by iridium-catalyzed three-component coupling reaction
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A convenient and efficient synthesis of substituted quinolines in a simple one-pot reaction of an arylamine 1, an aromatic aldehyde or aliphatic aldehyde 2 and an aliphatic aldehyde 3 in the presence of transition metal complexes or Lewis acids was developed. Among them, the iridium catalyst [Ir(cod)Cl] 2 catalyzed the reaction most efficiently. Copyright
- Igarashi, Takeyuki,Inada, Takashi,Sekioka, Tadao,Nakajima, Takayuki,Shimizu, Isao
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p. 106 - 107
(2007/10/03)
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- A Mild and Efficient One-Step Synthesis of Quinolines
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(Equation presented) The Friedlaender synthesis of quinolines is an extensively employed protocol, yielding the desired heterocycle in a two-step reduction-condensation sequence. We have developed a mild, efficient, high-yielding single-step variant of this methodology, which employs SnCl 2 and ZnCl2 to effect the reaction.
- McNaughton, Brian R.,Miller, Benjamin L.
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p. 4257 - 4259
(2007/10/03)
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- Selective conversion of diallylanilines and arylimines to quinolines
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A variety of diallylanilines are shown to undergo cobalt - carbonyl catalyzed rearrangement to quinolines. Diallylanilines are also used as allyl transfer reagents to convert benzaldimines into quinolines. Substitution in the 2- and 3-positions of the quinoline is featured in all transformations.
- Jacob, Josemon,Jones, William D.
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p. 3563 - 3568
(2007/10/03)
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- Ruthenium-catalyzed reductive cyclization of nitroarenes with trialkylamines leading to quinolines
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Nitroarenes react with trialkylamines in the presence of a catalytic amount of a ruthenium catalyst together with tin(H) chloride dihydrate at 180 °C in an aqueous medium (toluene-H2O) to afford the corresponding quinoles in moderate to good yields. The catalytic pathways seems to be proceeded via a sequence involving initial reduction of nitroarenes to anilines, alkyl group transfer from alkylamines to anilines to form an imine, dimerization of imine, and heterocyclization.
- Cho, Chan Sik,Kim, Tae Kyung,Kim, Bok Tae,Kim, Tae-Jeong,Shim, Sang Chul
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- Synthesis of quinolines via ruthenium-catalysed amine exchange reaction between anilines and trialkylamines
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Anilines react with an array of trialkylamines in the presence of a catalytic amount of RuCl3*nH2O and bis(diphenylphosphino)methane together with SnCl2*2H2O and hex-1-ene as hydrogen acceptor in dioxane at 180 deg C to afford the corresponding 2,3-disubstituted quinolines in moderate to good yields.
- Cho, Chan Sik,Oh, Byoung Ho,Kim, Joon Seok,Kim, Tae-Jeong,Shim, Sang Chul
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p. 1885 - 1886
(2007/10/03)
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- Diels-Alder reaction of 1,2,3-benzotriazine with enamine: Application to the synthesis of alkaloids, 2-propylquinoline and 2-pentylquinoline
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The Diels-Alder reaction of 1,2,3-benzotriazine with several pyrrolidine enamines of carbonyl compounds was carried out in chloroform in the presence of zinc bromide to afford 2- or 3-mono-, or 2,3-disubstituted quinolines. This method was applied to the synthesis of the alkaloids, 2-propylquinoline and 2-pentylquinoline.
- Koyama, Junko,Toyokuni, Izumi,Tagahara, Kiyoshi
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p. 332 - 334
(2007/10/03)
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- SYNTHESIS OF SUBSTITUTED QUINOLINES VIA THE CONDENSATION OF ANILINES WITH ALIPHATIC AND AROMATIC ALDEHYDES IN THE PRESENCE OF TRANSITION METAL AND RARE-EARTH METAL CATALYSTS
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Novel catalyst complexes derived from transition metal and rare-earth metal compounds have been developed for the condensation of anilines with aliphatic and aromatic aldehydes to give the corresponding 2,3-disubstituted quinolines in high yields.
- Dzhemilev, U. M.,Selimov, F. A.,Khusnutdinov, R. A.,Fatykhov, A. A.,Khalilov, L. M.,Tolstikov, G. A.
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p. 1248 - 1253
(2007/10/02)
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- Base-initiated oxidation of alkylindeneanilines by oxygen
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Oxidation and alkylation processes compete in the oxidative transformation of alkylindeneanilines in an alkaline medium.Oxidation leads mainly to the formation of formanilide anbd the corresponding carbonyl compound.Alkylation leads to a product which easily eliminates the aniline molecule with the formation of a derivative of the 1-aza-1,3-diene.A combination of alkylation and oxidation led to derivatives of quinoline.It is assumed that the alkylation-dehydrocyclization-elimination of alkylindeneanilines to quinolines by the action of oxygen and alkali is a variant of the Doebner-Miller reaction.During oxidation in the presence of sodium borohydride the products from conjugate oxidation-reductiono, i.e., the α-imino and β-amino alcohols, are also formed in addition to quinolines and oxidation and alkylation products.
- Grigoryan, G. S.,Tovmasyan, V. S.,Malkhasyan, A. Ts.,Martirosyan, G. T.,Beletskaya, I. P.
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- RUTHENIUM CATALYZED SYNTHESIS OF QUINOLINE DERIVATIVES FROM NITROARENES AND ALIPHATIC ALCOHOLS.
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Nitroarenes are reductively converted into quinoline derivatives with aliphatic alcohols in the presence of a catalytic amount of ruthenium compound at 180 degree C. Ruthenium(III) chloride is the most effective catalyst. The reaction of nitrobenzene with 1-propanol and 1-butanol gave 2-ethyl-3-methylquinoline and 3-ethyl-2-propylquinoline in 65 and 70% yields respectively. p-Methoxynitrobenzene gave 3-ethyl-6-methoxy-2-propyquinoline in 70% yield with 1-butanol. The reaction appears to include the redox reaction between the nitroarenes and the alcohols, that is, a catalytic hydrogen transfer reaction which generates the aminoarenes and aldehydes. Thus, the alcohol plays roles as both a reductant and an aldehyde precursor.
- Watanabe,Tsuji,Shida
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p. 435 - 438
(2007/10/02)
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- RUTHENIUM COMPLEX CATALYZED N-HETEROCYCLIZATION OF AMINOARENES TO QUINOLINE DERIVATIVES USING ALLYLIC ALCOHOLS AND ALIPHATIC ALDEHYDES.
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Aminoarenes reacted with 2-propen-1-ol and 2-buten-1-ol at 180 degree C to give quinoline derivatives in fairly good yields in the presence of a catalytic amount of a ruthenium complex. Dichlorotris(triphenylphosphine)-ruthenium was the most effective catalyst. THe aminoarenes with electron-releasing groups favored the formation of the quinolines. The N-heterocyclization also proceeded when aliphatic aldehydes were used in place of the allylic alcohols. The employment of allylic alcohols gave, however, higher yields in several cases. The reaction involves the isomerization of the allylic alcohols to the corresponding aldehydes. The aldehydes reacted with aminoarenes to give Schiff-base dimers which were then cyclized in the presence of the ruthenium complex to the quinolines. As a key intermediate in the reaction, the ortho-metallated species is proposed.
- Watanabe,Tsuji,Ohsugi,Shida
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p. 2452 - 2457
(2007/10/02)
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- The Transition Metal-catalyzed N-Alkylation and N-heterocyclization. A Reductive Transformation of Nitroarenes into (Dialkylamino)arenes and 2,3-Dialkyl-substituted Quinolines Using Aliphatic Aldehydes under Carbon Monoxide
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The catalytic N-alkylation and N-heterocyclization of nitroarenes occur at 180 deg C under a carbon monoxide pressure of 70 atm and in the presence of aldehyde and such transitionmetal complexes as rhodium and palladium complexes, thus giving 2,3-dialkyl-substituted quinolines and (dialkylamino)arenes in good yields.The product selectivity depends greatly on the catalysts: a binary catalyst, RhCl(PPh3)3 and PdCl2, is effective for the N-heterocyclization, while is effective for the N-alkylation.
- Watanabe, Yoshihisa,Suzuki, Naoki,Tsuji, Yasushi,Shim, Sang Chul,Mitsudo, Take-aki
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p. 1116 - 1120
(2007/10/02)
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- THE RUTHENIUM COMPLEX CATALYZED REDUCTIVE TRANSFORMATION OF NITROBENZENE. A NOVEL ROUTE TO 2,3-DIALKYLQUINOLINES AND N-ALKYLANILINES USING SATURATED ALCOHOLS
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Nitrobenzene reacts with saturated alcohols in the presence of a catalytic amount of ruthenium complex at 180 deg C to give 2,3-dialkylquinolines and N-alkylanilines in good yields.The reaction appears to include reduction of nitrobenzene with the alcohols by hydrogen transfer reaction.
- Watanabe, Yoshihisa,Tsuji, Yasushi,Suzuki, Naoki
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p. 1067 - 1068
(2007/10/02)
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- The Rhodium Complex-catalyzed Synthesis of Quinolines from Aminoarenes and Aliphatic Aldehydes
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A variety of aminoarenes react with aliphatic aldehydes in the presence of a catalytic amount of a rhodium complex and an excess amount of the corresponding nitroarenes at 180 deg C to give 2-alkyl- and 2,3-dialkyl-substituted quinolines in excellent yields.Among the rhodium complexes examined, 2 exhibits the highest activity as a catalyst.Thus, 2-methyl-, 2-ethyl-3-methyl-, 2-propyl-3-ethyl-, 2-butyl-3-propylquinoline derivatives are readily obtained from aminoarenes and ethanal, propanal, butanal, and pentanal respectively.
- Watanabe, Yoshihisa,Shim, Sang Chul,Mitsudo, Take-aki
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p. 3460 - 3465
(2007/10/02)
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- THE RUTHENIUM CATALYZED N-ALKYLATION AND N-HETEROCYCLIZATION OF ANILINE USING ALCOHOLS AND ALDEHYDES
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Aniline reacts with saturated and 2,3-unsaturated alcohols in the presence of ruthenium catalyst at 180 deg C to give N-alkylanilines and 2,3-alkylquinolines in good yields.
- Watanabe, Yoshihisa,Tsuji, Yasushi,Ohsugi, Yukihiro
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p. 2667 - 2670
(2007/10/02)
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