27356-52-1Relevant academic research and scientific papers
Ruthenium-catalyzed synthesis of quinolines from anilines and allylammonium chlorides in an aqueous medium via amine exchange reaction
Cho, Chan Sik,Kim, Joon Seok,Oh, Byoung Ho,Kim, Tae-Jeong,Shim, Sang Chul,Yoon, Nam Sik
, p. 7747 - 7750 (2000)
Anilines react with allylammonium chlorides in an aqueous medium (H2O-dioxane) in the presence of a catalytic amount of RuCl2(PPh3)3 together with SnCl2·2H2O to give the corresponding quinolines in moderate to good yields. The existence of SnCl2·2H2O is necessary for the effective formation of quinolines, and a reaction pathway involving amine exchange reaction between anilines and allylammonium chlorides to form an imine is proposed for this catalytic process. (C) 2000 Elsevier Science Ltd.
Aluminosilicates with Different Porous Structures in the Synthesis of 2-Ethyl-3-Methylquinoline
Grigor’eva,Kostyleva,Gataulin,Khazipova,Narender, Nama,Kutepov
, p. 719 - 725 (2019)
Abstract: The catalytic properties of microporous zeolites of different structural types (FAU, BEA, MOR, and MFI), a micro–meso–macroporous zeolite (H-Ymmm), and an ASM mesoporous aluminosilicate in the reaction of aniline with propionic aldehyde have been studied. It has been found that the reaction proceeds with a high conversion of aniline (90–99% over zeolites and 71% over an ASM aluminosilicate) to form two main products, namely, 2-ethyl-3-methylquinoline (2) and 2-ethyl-3-methyl-N-phenyl-1,2,3,4-tetrahydroquinoline-4-amine (3). The most selective catalysts for the synthesis of quinoline 2 are H-Y (up to 64%) and H-Ymmm (59%) zeolites and the ASM aluminosilicate (50%). It has been shown that an increase in the quinoline 2 selectivity is promoted by an increase in the catalyst acidity, in the reaction temperature to 160°C, in the catalyst concentration to 20 wt %, and in the aniline : aldehyde molar ratio to 1 : 2.
Oxygen-implanted MoS2 nanosheets promoting quinoline synthesis from nitroarenes and aliphatic alcohols via an integrated oxidation transfer hydrogenation-cyclization mechanism
Gao, Zhuyan,Huang, Zhipeng,Lu, Jianmin,Mu, Junju,Ren, Puning,Su, Kaiyi,Wang, Feng,Zhang, Chaofeng,Zhang, Shichao
, p. 1704 - 1713 (2022/03/08)
We herein report that MoS2 with oxygen-implanting modification (O-MoS2) can work as a multifunctional catalyst to achieve the one-pot quinoline synthesis from basic nitroarenes and aliphatic alcohols. Different from common knowledge that the application of MoS2-based catalysts and above quinoline synthesis need anaerobic conditions, we conduct the heterogeneous catalysis under an unusual air atmosphere. Catalyst characterization and experimental results indicate that the MoOx clusters implanted in the MoS2 skeleton, not the coordinatively unsaturated Mo sites (CUS Mo), dominate the generation of quinolines. By overturning the catalysis perception that O2 adsorption on MoSx can deactivate the MoS2-based catalysts using an efficient method for in situ healing of the MoOx structure in O-MoS2 and protecting the O-MoS2 catalyst by inhibiting unwanted MoOx elimination with extra H*, we innovatively introduce O2 into the quinoline synthesis. The robust O-MoS2 can be consecutively used ten times without regeneration and it offers 69-75% yields of 2-methylquinoline from nitrobenzene and ethanol. Furthermore, different from the traditional transfer hydrogenation-condensation mechanism, an integrated oxidation-transfer hydrogenation-cyclization mechanism is proposed over the O-MoS2 catalyst.
Mesoporous Aluminosilicates in the Synthesis of N-Heterocyclic Compounds
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
, p. 733 - 743 (2020/02/25)
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.
One-Pot Oxidative Synthesis of Substituted Quinolines from Alcohols and Arylamines Catalyzed by Fe(CrO2)2 in Water Medium
Makhmutov
, p. 1166 - 1172 (2018/10/24)
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.
Fe(CrO2)2-catalyzed, photoactivated oxidative one-pot tandem synthesis of substituted quinolines from primary alcohols and arylamines
Makhmutov, Aynur R.,Mustafin, Akhat G.,Usmanov, Salavat M.
, p. 369 - 374 (2018/05/28)
[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.
Heterogeneous catalytic synthesis of quinoline compounds from aniline and C1-C4 alcohols over zeolite-based catalysts
Huang, Chen,Li, An,Chao, Zi-Sheng
, p. 48275 - 48285 (2017/10/31)
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.
Synthesis of quinolines from aniline and propanol over modified USY zeolite: Catalytic performance and mechanism evaluated by: In situ Fourier transform infrared spectroscopy
Huang, Chen,Li, An,Li, Li-Jun,Chao, Zi-Sheng
, p. 24950 - 24962 (2017/07/10)
The reaction of aniline and propanol to quinolines was conducted in a fixed-bed flow-type reactor, using a series of modified USY zeolite catalysts. The structural, textural and acidic properties of the catalyst were characterized by XRD, N2-physisorption, 27Al MAS NMR, NH3-TPD and pyridine-FTIR, while the mechanism for the reaction of aniline and propanol was investigated by in situ FTIR. It was identified that the reaction of aniline and propanol generated predominantly quinolines, including 2-ethyl-3-methylquinoline and other alkyl quinoline, N-alkyl aniline and other byproducts. Among others, the ZnCl2/Ni-USY catalyst exhibited the best performance, providing a 96.4% conversion of aniline and a 78.3% total yield of quinolines with 81.2% total selectivity to quinolines and 60.1% selectivity to 2-ethyl-3-methylquinoline at 683 K. This was attributed to the larger concentration ratio of Lewis acid sites to Bronsted acid sites over the ZnCl2/Ni-USY catalyst, relative to other catalysts. There were predominantly two possible routes for the formation of quinolines, which required predominantly Lewis acid sites and Bronsted acid sites, respectively. In both the routes, N-phenylpropan-1-imine was proposed as the key intermediate. Relative to that based on Bronsted acid sites, the route based on Lewis acid sites appeared to contribute much more in the generation of quinolines from the reaction of aniline and propanol.
Synthesis of N-alkylanilines and substituted quinolines by reaction of aniline with alcohols and CCl4 effected with Ni-containing catalysts
Khusnutdinov,Baygusina,Aminov,Dzhemilev
experimental part, p. 690 - 693 (2012/10/08)
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.
Titania-supported iridium subnanoclusters as an efficient heterogeneous catalyst for direct synthesis of quinolines from nitroarenes and aliphatic alcohols
He, Lin,Wang, Jian-Qiang,Gong, Ya,Liu, Yong-Mei,Cao, Yong,He, He-Yong,Fan, Kang-Nian
supporting information; experimental part, p. 10216 - 10220 (2011/11/13)
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.
