16600-51-4Relevant articles and documents
Iridium-catalyzed synthesis of quinolines from 2-aminobenzyl alcohols with secondary alcohols
Yu,Yao,Hu,Wang
, p. 376 - 379 (2016)
The quinoline derivatives were synthesized from 2-aminobenzyl alcohols and secondary alcohols by the direct one-step synthesis using the iridium complexes as catalyst. This efficient and easy method is suitable for all kinds of substituted quinolines.
An improved synthesis of quinolines from β-bromovinyl aldehydes and primary arylamines in the presence of a palladium catalyst
Sik Cho, Chan,Bo Kim, Hyo,Ren, Wen Xiu,Yoon, Nam Sik
, p. 817 - 820 (2010)
β-Bromovinyl aldehydes are effectively cyclized with primary arylamines in DMF at 110 °C in the presence of a catalytic amount of a palladium catalyst to give the corresponding quinolines in high yields. Copyright
Low-valent titanium reagent-promoted intramolecular reductive coupling reactions of ketomalononitriles: A facile synthesis of benzo[4,5]indene, acridine and quinoline derivatives
Shi, Daqing,Rong, Liangce,Shi, Chunling,Zhuang, Qiya,Wang, Xiangshan,Tu, Shujiang,Hu, Hongwen
, p. 717 - 724 (2005)
The intramolecular reductive coupling reactions of ketomalononitriles induced by a low-valent titanium reagent were studied. Benzo[4,5]indene, acridine and quinoline derivatives are prepared in good yields under neutral and mild conditions.
Efficient red phosphorescent Ir(iii) complexes based on rigid ligands with high external quantum efficiency and low efficiency roll-off
Cheng, Jin-Feng,Fan, Jian,Fung, Man-Keung,Liu, Sheng-Nan,Tong, Kai-Ning,Zhao, Yue
, p. 6168 - 6175 (2020)
The rigid ligands in red phosphorescent Ir(iii) complexes can suppress the vibration and rotation around metal ions to maximize the utilization of low energy singlet and triplet states, thus greatly reducing the probability of non-radiative decay. In this paper, the coordination groups (phenyl and quinolinyl) are fused by a cyclohexyl group to produce rigidified ligands (5,6-dihydro-benzo[c]acridine and 9-fluoro-5,6-dihydro-benzo[c]acridine). A bulky ancillary ligand (2,2,6,6-tetramethylheptane-3,5-dione) was applied for the synthesis of Ir(iii) complexes (Ir-DHBA and Ir-F-DHBA) to minimize the intimate interactions between Ir(iii) molecules and consequently to reduce triplet-triplet annihilation and triplet-polaron annihilation. When the two Ir(iii) complexes were applied as dopants in organic light-emitting diode (OLED) devices, they both showed excellent electroluminescence (EL) performance. The device based on Ir-DHBA demonstrated a low efficiency roll-off with a maximum external quantum efficiency (EQE) of 26.0%, 25.3% EQE at a brightness of 1000 cd m-2 and 22.7% EQE at 10?000 cd m-2. The device based on Ir-F-DHBA (at a doping ratio of 3%) with an exciplex as a co-host showed a maximum EQE of over 28% with Commission Internationale de l'Eclairage (CIE) coordinates of (0.61, 0.39) and an EL emission peak at 600 nm.
Nickel-catalyzed α-alkylation of ketones with benzyl alcohols
Wu, Di,Wang, Yubin,Li, Min,Shi, Lei,Liu, Jichang,Liu, Ning
, (2021/11/04)
We reported an efficient method for α-alkylation of ketones with benzyl alcohols using the pyridine-bridged pincer-type N-heterocyclic carbenes nickel complexes as catalysts. A wide range of ketones and benzyl alcohols were efficiently converted into various alkylated products in moderate to high yields. In addition, these nickel complexes were also successfully applied for the synthesis of a wide range of quinoline derivatives.
Visible-Light-Mediated Oxidative Cyclization of 2-Aminobenzyl Alcohols and Secondary Alcohols Enabled by an Organic Photocatalyst
Xu, Jing-Xiu,Pan, Nan-Lian,Chen, Jia-Xi,Zhao, Jin-Wu
, p. 10747 - 10754 (2021/08/16)
This paper describes a visible-light-mediated oxidative cyclization of 2-aminobenzyl alcohols and secondary alcohols to produce quinolines at room temperature. This photocatalytic method employed anthraquinone as an organic small-molecule catalyst and DMSO as an oxidant. According to this present procedure, a series of quinolines were prepared in satisfactory yields.
Direct synthesis of ring-fused quinolines and pyridines catalyzed byNNHY-ligated manganese complexes (Y = NR2or SR)
Han, Mingyang,Lin, Qing,Liu, Qingbin,Liu, Song,Ma, Ning,Solan, Gregory A.,Sun, Wen-Hua,Wang, Zheng,Yan, Xiuli
, p. 8026 - 8036 (2021/12/27)
Four cationic manganese(i) complexes, [(fac-NNHN)Mn(CO)3]Br (Mn-1-Mn-3) and [(fac-NNHS)Mn(CO)3]Br (Mn-4) (whereNNHis a 5,6,7,8-tetrahydro-8-quinolinamine moiety), have been synthesized and evaluated as catalysts for the direct synthesis of quinolines and pyridines by the reaction of a γ-amino alcohol with a ketone or secondary alcohol;NNHS-ligatedMn-4proved the most effective of the four catalysts. The reactions proceeded well in the presence of catalyst loadings in the range 0.5-5.0 mol% and tolerated diverse functional groups such as alkyl, cycloalkyl, alkoxy, chloride and hetero-aryl. A mechanism involving acceptorless dehydrogenation coupling (ADC) has been proposed on the basis of DFT calculations and experimental evidence. Significantly, this manganese-based catalytic protocol provides a promising green and environmentally friendly route to a wide range of synthetically important substituted monocyclic, bicyclic as well as tricyclicN-heterocycles (including 50 quinoline and 26 pyridine examples) with isolated yields of up to 93%.
Mild and efficient copper-catalyzed oxidative cyclization of oximes with 2-aminobenzyl alcohols at room temperature: synthesis of polysubstituted quinolines
Liu, Yan-Yun,Wei, Yang,Huang, Zhi-Hui,Liu, Yilin
supporting information, p. 659 - 666 (2021/02/06)
A simple and efficient ligand-free Cu-catalyzed protocol for the synthesis of polysubstituted quinolinesviaoxidative cyclization of oxime acetates with 2-aminobenzyl alcohols at room temperature has been developed. The presented approach provides a new synthetic pathway leading to polysubstituted quinolines with good functional group tolerance under mild conditions. Moreover, this transformation can be applied for the preparation of quinolines on a gram scale. Oxime acetates serve as the internal oxidants in the reactions, thus making this method very attractive.
Copper-catalyzed formal [3 + 3] annulations of arylketoximes and o-fluorobenzaldehydes: An entry to quinoline compounds
Xu, Zhenhua,Chen, Hongbiao,Deng, Guo-Jun,Huang, Huawen
supporting information, p. 936 - 942 (2021/02/01)
A copper-based catalytic system has been developed to enable efficient cyclization of ketoxime acetates with ofluorobenzaldehydes. This protocol offers an efficient method for the synthesis of substituted quinoline derivatives with a broad range of compatible functionalities. The present system also provides a rapid access to synthetically and pharmaceutically useful quinoline-fused polycycles such as benzo[c]acridines.
Designed pincer ligand supported Co(ii)-based catalysts for dehydrogenative activation of alcohols: Studies onN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines
Singh, Anshu,Maji, Ankur,Joshi, Mayank,Choudhury, Angshuman R.,Ghosh, Kaushik
, p. 8567 - 8587 (2021/06/30)
Base-metal catalystsCo1,Co2andCo3were synthesized from designed pincer ligandsL1,L2andL3having NNN donor atoms respectively.Co1,Co2andCo3were characterized by IR, UV-Vis. and ESI-MS spectroscopic studies. Single crystal X-ray diffraction studies were investigated to authenticate the molecular structures ofCo1andCo3. CatalystsCo1,Co2andCo3were utilized to study the dehydrogenative activation of alcohols forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines. Under optimized reaction conditions, a broad range of substrates including alcohols, anilines and ketones were exploited. A series of control experiments forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines were examined to understand the reaction pathway. ESI-MS spectral studies were investigated to characterize cobalt-alkoxide and cobalt-hydride intermediates. Reduction of styrene by evolved hydrogen gas during the reaction was investigated to authenticate the dehydrogenative nature of the catalysts. Probable reaction pathways were proposed forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines on the basis of control experiments and detection of reaction intermediates.
