5855-65-2Relevant academic research and scientific papers
Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines
Talvitie, Juulia,Alanko, Iida,Bulatov, Evgeny,Koivula, Juho,P?ll?nen, Topias,Helaja, Juho
supporting information, p. 274 - 278 (2022/01/04)
Visible-light-excited 9,10-phenanthrenequinone (PQ*) was used as a photocatalyst for the synthesis of polysubstituted quinolines via the electrocyclization of 2-vinylarylimines. Up to quantitative yields of 2,4-disubstituted quinolines were received after 1 h of excitation with blue LEDs at room temperature when MgCO3 was used as an additive in DCM. On the basis of experimental and DFT studies, we propose that PQ? induces one-electron oxidation of the imine substrate that triggers the electrocyclization mechanism.
Carbocatalytic Cascade Synthesis of Polysubstituted Quinolines from Aldehydes and 2-Vinyl Anilines
Bulatov, Evgeny,Helaja, Juho,Hu, Tao,Lenarda, Anna,M?kel?, Mikko K.,Malinen, Kiia,Melchionna, Michele,Nieger, Martin,Talvitie, Juulia,Wirtanen, Tom
, p. 3775 - 3782 (2021/07/20)
Oxidized active carbon (oAC) catalyses the formation of polysubstituted quinolines from o-vinyl anilines and aldehydes. The reaction proceeds in a cascade manner through condensation, electrocyclization and dehydrogenation, and gives access to a wide range of quinolines with alkyl and/or aryl substituents as demonstrated with 40 examples. The metal-free catalytic procedure allows a heterogeneous protocol for the synthesis of various polysubstituted quinolines. The mechanistic studies imply that both the acid and quinoidic groups in oAC are integral for the catalytic manifold. (Figure presented.).
Synthesis of new quinolizinium-based fluorescent compounds and studies on their applications in photocatalysis
Chan, Wing-Cheung,Deng, Jie-Ren,Ko, Ben Chi-Bun,Tantipanjaporn, Ajcharapan,Wong, Man-Kin,Yip, Wai-Ming,Yu, Qiong
supporting information, p. 8507 - 8515 (2021/10/20)
Quinoliziniums, cationic aromatic heterocycles bearing a quaternary bridgehead nitrogen, have been widely used as fluorescent dyes, DNA intercalators, ionic liquidsetc. A library of new quinolizinium compounds was synthesized from quinolines and internal alkyne substrates in up to 65% isolated yields. Systematic studies of their photophysical properties were conducted. The quinoliziniums have been used in three visible-light-induced photocatalysis reactions with good yields.
Synthesis of 2,4-Diarylquinoline Derivatives via Chloranil-Promoted Oxidative Annulation and One-Pot Reaction
Cheng, Dongping,Pu, Yueqi,Shen, Jing,Xu, Xiaoliang,Yan, Jizhong,Yan, Xianhang
, p. 1833 - 1840 (2020/06/08)
An oxidative annulation for the synthesis of 2,4-diarylquinolines from o -allylanilines is disclosed that uses recyclable reagent Chloranil as the oxidant. The corresponding products are obtained in moderate to excellent yields. Furthermore, a one-pot access to 2,4-di aryl quinolines from easily available anilines and 1,3-diarylpropenes is described as a highly atom-efficient protocol that involves oxidative coupling, rearrangement, and oxidative annulation.
Mn(III)-Mediated Regioselective 6-endo-trig Radical Cyclization of o-Vinylaryl Isocyanides to Access 2-Functionalized Quinolines
Liu, Yan,Li, Shi-Jun,Chen, Xiao-Lan,Fan, Lu-Lu,Li, Xiao-Yun,Zhu, Shan-Shan,Qu, Ling-Bo,Yu, Bing
, p. 688 - 694 (2020/01/02)
A Mn(III)-mediated radical cyclization reaction of o-vinylaryl isocyanides and arylboronic acids or diphenylphosphine oxides to access various 2-functionalized quinolines under mild conditions was developed. With the introduction of radical stabilizing substituents (e. g. aryl and methyl group) on vinyl group, this reaction provides a regiospecific 6-endo-trig radical cyclization of o-vinylaryl isocyanides, giving a number of structurally unique and biologically potential 2-functionalized quinoline derivatives.
Palladium-Catalyzed/Copper-Mediated Desulfurization and Aryl- ation of Quinoline-2-(1 H)-thione for Rapid Access to Quinoline Derivatives
Guo, Fu-Hu,Lu, Hai-Long,Quan, Zheng-Jun,Wang, Tong-Lin,Wang, Xi-Cun
, p. 893 - 900 (2020/03/13)
An efficient method for carbon-carbon bond formation is described. The process employs the palladium-catalyzed and copper-mediated cross-coupling of quinoline-2-(1 H)-thiones with arylboronic acids or alkynes through C-S bond cleavage without an inert atm
Quinoline compound and synthesis method thereof
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Paragraph 0105-0109, (2020/02/14)
The invention discloses a synthesis method of a quinoline compound. The synthesis method comprises the following steps: adding a diazocarbonyl compound and a 2-vinylaniline compound into a solvent, carrying out a reaction under the protection of an inert
Green synthesis of quinolines via A3-coupling by using graphene oxide-supported Br?nsted acidic ionic liquid
Gajare, Shivanand,Patil, Audumbar,Hangirgekar, Shankar,Dhanmane, Sushilkumar,Rashinkar, Gajanan
, p. 2417 - 2436 (2020/02/18)
Abstract: Graphene oxide-supported Bronsted acidic ionic liquid ([GrBenzImi]SO3H) has been prepared by covalent grafting of benzimidazole unit in the matrix of graphene oxide followed by reaction with 1,4-butane sultone and hydrochloric acid. [GrBenzImi]SO3H has been characterized by various techniques including Fourier transform infrared spectroscopy (FTIR), FT-Raman (FT-Raman spectroscopy), CP-MAS 13C NMR spectroscopy, thermogravimetric analysis, energy-dispersive X-ray analysis, Brunauer–Emmett–Teller surface area, X-ray diffraction, and transmission electron microscopy. [GrBenzImi]SO3H was successfully employed as heterogeneous catalyst in A3-coupling reaction of aryl aldehydes, anilines and phenylacetylene for the synthesis of 2,4-disubstituted quinolines using water/ethanol system (1:1) as green medium. [GrBenzImi]SO3H could be recycled six times without significant loss in the yield of product. Graphic abstract: [Figure not available: see fulltext.].
MOF-5 as a highly efficient and recyclable catalyst for one pot synthesis of 2,4-disubstituted quinoline derivatives
Di, Jia-Qi,Ma, Cui-Ting,Xiao, Song-Tao,Zhang, Zhan-Hui
, p. 8614 - 8620 (2020/06/09)
A MOF-5-catalyzed three-component coupling reaction was developed as an efficient approach for the synthesis of 2,4-disubstituted quinoline derivatives via a one pot three-component reaction of aromatic amines, aldehydes and alkynes with excellent yields. The easy recovery and reusability of the catalyst, broad substrate scope, short reaction time, high yields of products and solvent-free conditions make this protocol practical, environmentally friendly and economically attractive.
Synthesis method of 2, 4-diarylquinoline compound
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Paragraph 0056-0068, (2020/06/20)
The invention relates to a synthesis method of a 2, 4-diarylquinoline compound (II), which comprises the following steps: mixing a compound represented by a formula (I), an oxidizing agent and an organic solvent, heating to 60-80 DEG C, reacting for 1-2 hours, and carrying out after-treatment on the reaction solution to obtain a product (II). According to the synthesis method, a metal and other additives are not needed, operation is easy, raw materials are easy to obtain, and conditions are mild.
