120-15-0Relevant articles and documents
Fine tuning of Pd0 nanoparticle formation on hydroxyapatite and its application for regioselective quinoline hydrogenation
Hashimoto, Norifumi,Takahashi, Yusuke,Hara, Takayoshi,Shimazu, Shogo,Mitsudome, Takato,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
, p. 832 - 834 (2010)
Fine control of the formation of Pd0 nanoparticles with diameters between 1 and 1.5nm on hydroxyapatite (HAP) was achieved by adjusting the temperature at which the PdII species on the HAP surface (Pd IIHAP) was reduced in the presence of 1 atm of molecular hydrogen. The HAP-supported Pd0 nanoparticles (Pd0HAP) having an average diameter of 1.5 nm exhibited significantly high catalytic activity for the regioselective hydrogenation of quinolines to the corresponding 1,2,3,4-tetrahydroquinolines under mild reaction conditions. Moreover, the Pd0HAP catalyst was reusable without appreciable loss of its high catalytic activity or selectivity.
Selective reduction of condensed N-heterocycles using water as a solvent and a hydrogen source
Cho, Hyejin,T?r?k, Fanni,T?r?k, Béla
, p. 1209 - 1215 (2013)
The reduction of unprotected indoles and quinolines is described using water as a hydrogen source. The method is based on the application of a RANEY type Ni-Al alloy in an aqueous medium. During the reaction the Al content of the alloy, used as reductants, reacts with water in situ providing hydrogen and a RANEY Ni catalyst, thus the alloy serves as a hydrogen generator as well as a hydrogenation catalyst. The simplicity and efficacy of the method are illustrated by the selective reduction of a variety of substituted indoles and quinolines to indolines and tetrahydroquinolines, respectively.
Regio- and chemoselective transfer hydrogenation of quinolines catalyzed by a Cp*Ir complex
Fujita, Ken-Ichi,Kitatsuji, Chihiro,Furukawa, Shigetoyo,Yamaguchi, Ryohei
, p. 3215 - 3217 (2004)
An efficient method for the transfer hydrogenation of quinolines catalyzed by a Cp*Ir complex was developed. A variety of 1,2,3,4-tetrahydroquinolines were obtained by regio- and chemoselective transfer hydrogenation of quinolines using 2-propanol as a hydrogen source.
Utilization of renewable formic acid from lignocellulosic biomass for the selective hydrogenation and/or N-methylation
Zhou, Chao-Zheng,Zhao, Yu-Rou,Tan, Fang-Fang,Guo, Yan-Jun,Li, Yang
, p. 4724 - 4728 (2021)
Lignocellulosic biomass is one of the most abundant renewable sources in nature. Herein, we have developed the utilization of renewable formic acid from lignocellulosic biomass as a hydrogen source and a carbon source for the selective hydrogenation and further N-methylation of various quinolines and the derivatives, various indoles under mild conditions in high efficiencies. N-methylation of various anilines is also developed. Mechanistic studies indicate that the hydrogenation occurs via a transfer hydrogenation pathway.
An unusual chemoselective hydrogenation of quinoline compounds using supported gold catalysts
Ren, Dong,He, Lin,Yu, Lei,Ding, Ran-Sheng,Liu, Yong-Mei,Cao, Yong,He, He-Yong,Fan, Kang-Nian
, p. 17592 - 17598,7 (2012)
The pursuit of modern sustainable chemistry has stimulated the development of innovative catalytic processes that enable chemical transformations to be performed under mild and clean conditions with high efficiency. Herein, we report that gold nanoparticles supported on TiO2 catalyze the chemoselective hydrogenation of functionalized quinolines with H2 under mild reaction conditions. Our results point toward an unexpected role for quinolines in gold-mediated hydrogenation reactions, namely that of promoter; this is in stark contrast to what prevails in the traditional noble metal Pd-, Pt-, and Ru-based catalyst systems, in which quinolines and their derivatives typically act as poisons. As a result of the remarkable promotional effect of quinoline molecules to H2 activation over supported gold, the transformation can proceed smoothly under very mild conditions (even at temperatures as low as 25 °C). Of practical significance is that various synthetically useful functional groups including halogens, ketone, and olefin remain intact during the hydrogenation of quinolines. Moreover, the protocol also shows promise for the regiospecific hydrogenation of the heterocyclic ring of a variety of other biologically important heteroaromatic nitrogen compounds, such as isoquinoline, acridine, and 7,8-benzoquinoline, in a facile manner. Apart from its importance in catalytic hydrogenation, we believe that this intriguing self-promoted effect by reactant molecules may have fundamental implications for the broad field of gold catalysis and form the basis for development of new catalytic procedures for other key transformations.
High efficient iron-catalyzed transfer hydrogenation of quinolines with Hantzsch ester as hydrogen source under mild conditions
He, Renke,Cui, Peng,Pi, Danwei,Sun, Yan,Zhou, Haifeng
, p. 3571 - 3573 (2017)
A highly efficient transfer hydrogenation of quinolines with Hantzsch ester as hydrogen source in the presence of 1 mol% Fe(OTf)2 under mild conditions has been developed. A series of substituted 1,2,3,4-tetrahydroquinoline derivatives were afforded in excellent yields with good functional group tolerance.
Reduction of quinolines to 1,2,3,4-tetrahydro derivatives employing a combination of NaCNBH3 and BF3.OEt2
Srikrishna, Adusumilli,Reddy, T. Jagadeeswar,Viswajanani, Ranganathan
, p. 1631 - 1636 (1996)
A regiospecific reduction of quinolines (and 1,10-phenanthroline) into the corresponding 1,2,3,4-tetrahydro derivatives using a combination of sodium cyanoborohydride and boron trifluoride etherate in refluxing methanol is described. Under the same conditions indole and acridine reduced to the corresponding dihydroderivatives, whereas acyl group transfer from oxygen to nitrogen atom is also noticed in the case of 8-acyloxyquinolines.
Efficient Hydrogenation of Nitrogen Heterocycles Catalyzed by Carbon-Metal Covalent Bonds-Stabilized Palladium Nanoparticles: Synergistic Effects of Particle Size and Water
Zhang, Yu,Zhu, Jie,Xia, Yun-Tao,Sun, Xiao-Tao,Wu, Lei
, p. 3039 - 3045 (2016)
We reveal here the first hydrogenation of nitrogen heterocycles catalyzed by carbon–metal covalent bonds-stabilized palladium nanoparticles in water under mild conditions. Using a one-phase reduction method, smaller metal–carbon covalent bond-stabilized Pd nanoparticles were prepared with a size distribution of 2.5±0.5 nm, which showed extraordinary synergistic effects with water in the catalytic hydrogenation of nitrogen heterocycles. Water was supposed to accelerate substrate absorption and synergistic activation of molecular hydrogen on the Pd nanoparticles surface. The nanosized Pd catalyst could be easily recovered and reused for 5 runs. (Figure presented.).
Tuning chemical compositions of bimetallic AuPd catalysts for selective catalytic hydrogenation of halogenated quinolines
Zhang, Sai,Xia, Zhaoming,Ni, Ting,Zhang, Huan,Wu, Chao,Qu, Yongquan
, p. 3260 - 3266 (2017)
Catalytic hydrogenation of halogenated quinolines is a longstanding challenge due to the harsh reaction conditions and disillusionary chemoselectivity owing to dehalogenation. Exploration of novel catalytic materials is still a big challenge. Herein, density functional theory calculations indicate that halogenated quinolines are selectively adsorbed on the Au surface via the nitrogen atom in the tilted orientation and on Pd via the quinoline ring in the flat orientation. In the tilted orientation, the C-Cl bond is away from the surface of catalysts, which can avoid the hydrogenation of the C-Cl bond by the surface activated hydrogen species. A series of Au1?xPdx bimetallic catalysts were deposited on CeO2 nanorods by a facile electroless chemical deposition method. The Au1?xPdx catalysts with low Pd content delivered enhanced activity and improved chemoselectivity for the hydrogenation of halogenated quinolines. Highly dispersed Pd in the Au matrix of bimetallic catalysts with low Pd content triggers hydrogen activation on Pd sites and leads to the selective adsorption of halogenated quinolines on Au sites in the tilted orientation. The generated active hydrogen species can diffuse from Pd to Au sites for the hydrogenation of the tilted halogenated quinolines, resulting in suppressed dehalogenation and high chemoselectivity to the expected products.
Rational design, synthesis, anti-HIV-1 RT and antimicrobial activity of novel 3-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)-1-(piperazin-1-yl)propan-1-one derivatives
Chander, Subhash,Wang, Ping,Ashok, Penta,Yang, Liu-Meng,Zheng, Yong-Tang,Murugesan, Sankaranarayanan
, p. 75 - 83 (2016)
In the present study, fifteen novel 3-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)-1-(piperazin-1-yl)propan-1-one (6a-o) derivatives were designed as inhibitor of HIV-1 RT using ligand based drug design approach and in-silico evaluated for drug-likeness properties. Designed compounds were synthesized, characterized and in-vitro evaluated for RT inhibitory activity against wild HIV-1 RT strain. Among the tested compounds, four compounds (6a, 6b, 6j and 6o) exhibited significant inhibition of HIV-1 RT (IC50 ≤ 10 μg/ml). All synthesized compounds were also evaluated for anti-HIV-1 activity as well as cytotoxicity on T lymphocytes, in which compounds 6b and 6l exhibited significant anti-HIV activity (EC50 values 4.72 and 5.45 μg/ml respectively) with good safety index. Four compounds (6a, 6b, 6j and 6o) found significantly active against HIV-1 RT in the in-vitro assay were in-silico evaluated against two mutant RT strains as well as one wild strain. Further, titled compounds were evaluated for in-vitro antibacterial (Escherichia coli, Pseudomonas putida, Staphylococcus aureus and Bacillus cereus) and antifungal (Candida albicans and Aspergillus Niger) activities.
