64388-15-4Relevant academic research and scientific papers
Direct C-H Arylation and Alkylation of Electron-Deficient Heteroaromatic Compounds with Organozinc Reagents
Peng, Zhihua,Yu, Chuanman,Wang, Yilei,Wei, Dongyue,Jiang, Cuiyu
, p. 3678 - 3688 (2021/11/16)
A direct and convenient method for the C-H arylation and alkylation of electron-deficient N-heteroarenes with readily available organozinc reagents has been developed. This transformation could be readily performed in the absence of a transition-metal catalyst and external oxidants, affording a wide range of substituted heteroarenes with good functional group tolerance in good to excellent yields. The developed simple protocol is scalable to the gram level and suitable for late-stage modification of bioactive molecules and drugs.
Iron Single Atom Catalyzed Quinoline Synthesis
Chen, Zhongxin,Song, Jingting,Peng, Xinwen,Xi, Shibo,Liu, Jia,Zhou, Wenhui,Li, Runlai,Ge, Rile,Liu, Cuibo,Xu, Haisen,Zhao, Xiaoxu,Li, Haohan,Zhou, Xin,Wang, Lu,Li, Xing,Zhong, Linxin,Rykov, Alexandre I.,Wang, Junhu,Koh, Ming Joo,Loh, Kian Ping
, (2021/07/21)
The production of high-value chemicals by single-atom catalysis is an attractive proposition for industry owing to its remarkable selectivity. Successful demonstrations to date are mostly based on gas-phase reactions, and reports on liquid-phase catalysis are relatively sparse owing to the insufficient activation of reactants by single-atom catalysts (SACs), as well as, their instability in solution. Here, mechanically strong, hierarchically porous carbon plates are developed for the immobilization of SACs to enhance catalytic activity and stability. The carbon-based SACs exhibit excellent activity and selectivity (≈68%) for the synthesis of substituted quinolines by a three-component oxidative cyclization, affording a wide assortment of quinolines (23 examples) from anilines and acetophenones feedstock in an efficient, atom-economical manner. Particularly, a Cavosonstat derivative can be synthesized through a one-step, Fe1-catalyzed cyclization instead of traditional Suzuki coupling. The strategy is also applicable to the deuteration of quinolines at the fourth position, which is challenging by conventional methods. The synthetic utility of the carbon-based SAC, together with its reusability and scalability, renders it promising for industrial scale catalysis.
Visible-light-induced photoxidation-Povarov cascade reaction: synthesis of 2-arylquinoline through alcohol andN-benzylanilines under mild conditionsviaAg/g-C3N4nanometric semiconductor catalyst
Wang, Peng,Wang, Xiaowen,Niu, Xiyu,Zhu, Li,Yao, Xiaoquan
supporting information, p. 4840 - 4843 (2020/05/13)
With a Ag/g-C3N4nanometric semiconductor as the photocatalyst, 2-arylquinolines were synthesized through a photoxidation-Povarov cascade reaction ofN-benzylanilines and alcohols under visible light irradiation. Under the blue light of a 3 W LED, good yields were achieved for various substrates in oxygen at room temperature. This methodology provides a green and mild alternative for the formation of 2-arylquinoline derivatives. Remarkably, the Ag/g-C3N4nanocomposite can be conveniently recovered and reused several times with satisfying yields.
Facile synthesis of substituted quinolines by iron(iii)-catalyzed cascade reaction between anilines, aldehydes and nitroalkanes
Mahato, Sachinta,Mukherjee, Anindita,Santra, Sougata,Zyryanov, Grigory V.,Majee, Adinath
, p. 7907 - 7917 (2019/09/06)
A library of substituted quinolines has been synthesized by the reaction of aldehydes, anilines and nitroalkanes using a catalytic amount of Fe(iii) chloride. The reaction is a simple, efficient, one-pot, three-component domino strategy in ambient air which afforded the products in high yields. A probable pathway of the reaction is a sequential aza-Henry reaction/cyclization/denitration. The use of commercially available chemicals as starting materials, an inexpensive metal catalyst, aerobic reaction conditions, tolerance of a wide range of functional groups, and operational simplicity are the notable advantages of this present protocol.
On-Water Synthesis of 2-Substituted Quinolines from 2-Aminochalcones Using Benzylamine as the Nucleophilic Catalyst
Lee, So Young,Cheon, Cheol-Hong
, p. 13036 - 13044 (2018/11/20)
On-water synthesis of 2-substituted quinolines from 2-aminochalcone derivatives was developed using benzylamine as the nucleophilic catalyst. Various 2-aminochalcones could be applied to this protocol, and the desired 2-substituted quinoline products were isolated in excellent yields by simple filtration. Furthermore, we elucidated the role of benzylamine in this transformation and provided the detailed reaction mechanism. This protocol has several additional advantages, such as simple operation, broad substrate scope, good functional group tolerance, easy product isolation, recycling of the catalyst, and gram-scale synthesis.
Synthesis of 2-Substituted Quinolines from 2-Aminostyryl Ketones Using Iodide as a Catalyst
Lee, So Young,Jeon, Jiye,Cheon, Cheol-Hong
, p. 5177 - 5186 (2018/05/15)
A new protocol for the synthesis of 2-substituted quinolines from 2-aminostyryl ketones has been developed using iodide as a nucleophilic catalyst. Conjugate addition of iodide to 2-aminostyryl ketones yielded the corresponding β-iodoketones, which could have a conformation where the amino and carbonyl groups are proximal through free rotation about the Cα-Cβ single bond. Subsequent condensation between the amino and carbonyl groups followed by elimination of hydrogen iodide provided the corresponding quinolines, with regeneration of the iodide catalyst.
Enantioselective Synthesis of Tetrahydroquinolines from 2-Aminochalcones via a Consecutive One-Pot Reaction Catalyzed by Chiral Phosphoric Acid
Park, Do Young,Lee, So Young,Jeon, Jiye,Cheon, Cheol-Hong
, p. 12486 - 12495 (2018/10/24)
A new asymmetric protocol for the synthesis of chiral tetrahydroquinolines from 2-aminochalcones via a two-step one-pot consecutive process (cyclization/asymmetric reduction) has been developed using chiral phosphoric acid as the sole catalyst. 2-Aminochalcones were converted into the corresponding quinolines through chiral phosphoric acid-catalyzed dehydrative cyclization, and the resultant quinolines were subsequently reduced to the chiral tetrahydroquinolines via chiral phosphoric acid-catalyzed asymmetric reduction with Hantzsch ester. Various 2-aminochalcones could be applicable to this protocol, and the desired tetrahydroquinolines were obtained in excellent yields and with excellent enantioselectivities. Furthermore, the utility of this protocol has been successfully demonstrated in the highly efficient synthesis of estrogen receptor modulator.
Three-Component Povarov Reaction with Alcohols as Alkene Precursors: Efficient Access to 2-Arylquinolines
Li, Xinjian,Xing, Qi,Li, Pan,Zhao, Jingjing,Li, Fuwei
supporting information, p. 618 - 625 (2017/02/05)
An atom-economic and efficient approach to the synthesis of 2-arylquinolines has been developed. The protocol involves an iron-catalysed cascade N-alkylation/aerobic oxidation/Povarov reaction, and the desired quinolines were prepared in moderate to excellent yields from readily accessible anilines, aldehydes, and EtOH/nPrOH, with water as the only side-product. The aniline substrates also act as a recyclable transfer medium for EtOH/nPrOH through an in-situ N-alkylation/oxidation process. This makes EtOH/nPrOH an economical and environmentally friendly precursor of alkenes as well as the solvent.
One-pot synthesis and fluorescence properties of 2-arylquinolines
Sueki, Shunsuke,Okamoto, Chiharu,Shimizu, Isao,Seto, Keisuke,Furukawa, Yukio
supporting information; experimental part, p. 385 - 390 (2010/07/09)
The one-pot synthesis of 2-arylquinoline with arylamines, arylaldehyde, and 1,1-diethoxyethane were studied using a catalytic amount ytterbium triflate. Various 2-arylquinolines showed fluorescence properties and the fluorescence was quenched by introduci
