906463-83-0Relevant academic research and scientific papers
Cascade embedding triethyltryptophanium iodide ionic liquid (TrpEt3+I?) on silicated titanomagnetite core (Fe3-xTixO4-SiO2@TrpEt3+I?): A novel nano organic–inorganic hybrid to prepare a library of 4-substituted quinoline-2-carboxylates and 4,6-disubstituted quinoline-2-carboxylates
Nikoofar, Kobra,Molaei Yielzoleh, Fatemeh
, p. 1549 - 1562 (2021/05/06)
A library of substituted quinolone-2-carboxylates (4,6-disubstituted quinolone-2-carboxylates, 6-substituted quinoline dialkyl-2,4-dicarboxylates, and 6-substituted 4-[2-methoxy-2-oxoethyl]quinoline-2-methylcarboxylates) was obtained through different scopes of one-pot and one-step MCRs such as (a) three-component reaction of aromatic amines, dialkyl acetylenedicarboxylates, and terminal alkenes/ketones; (b) pseudo three-component reaction of anilines and dialkyl acetylenedicarboxylates; and (c) pseudo three-component reaction of anilines and methyl propiolate under solvent-free conditions at 100°C. The promoter of these annulation processes is a novel inorganic–organic core–shell that was obtained from silicated titanomagnetite, tryptophan amino acid, and ethyl iodide. The tryptophan embedded on the silicated titanomagnetite core (Fe3-xTixO4-SiO2) followed by alkylation with ethyl iodide subsequently result in in situ preparation of triethyltryptophanium iodide ionic liquid (TrpEt3+I?). The final nanohybrid (Fe3-xTixO4-SiO2@TrpEt3+I?) was characterized by field-emission scanning electron microscope, EDAX, FT-IR, TGA/DTG, vibrating sample magnetometer, and X-ray fluorescence techniques. The highlighted features of the protocol are as follows: (a) synthesis of a vast range of substituted quinolines through a straightforward method from simple substrates under solvent-free conditions, (b) utilizing various scopes of functionalities as substrates, (c) simple separation of the nano promoter via an external magnet, (d) regioselectivity in the cascade annulation procedure, and (e) recovery and reusability of the nanocomposite within three runs without significant activity loss.
A Heck reaction/photochemical alkene isomerization sequence to prepare functionalized quinolines
Donohoe, Timothy J.,Hoff, Oskar,Hoffman, Jack B.,Kelly, Alex,Walker, Johannes C. L.,Werrel, Simon
, (2020/08/06)
A route to prepare functionalized quinolines based on a Heck reaction/UV-induced alkene isomerization sequence is described. The method allows for the preparation of quinolines under mild and neutral conditions and has broad functional group tolerance. Acid-sensitive functional groups that would not be tolerated under previous approaches can be included and a one-pot quinoline forming procedure is also reported.
One-pot synthesis of 2,4-disubstituted quinolines via silver-catalyzed three-component cascade annulation of amines, alkyne esters and terminal alkynes
Li, Yunlan,Zhang, Qiurui,Xu, Xuefeng,Zhang, Xu,Yang, Yurong,Yi, Wei
, p. 965 - 970 (2019/03/13)
Described herein is a new and general method for one-pot synthesis of 2,4-disubstituted quinolines via silver-catalyzed [3 + 1 + 2] annulation of simple amines, alkyne esters and terminal alkynes. The versatile transformation might initiate with the facil
Cleavage of C-C Bonds for the Synthesis of C2-Substituted Quinolines and Indoles by Catalyst-Controlled Tandem Annulation of 2-Vinylanilines and Alkynoates
Ni, Jixiang,Jiang, Yong,An, Zhenyu,Yan, Rulong
, p. 1534 - 1537 (2018/03/23)
The strategy for the synthesis of C2-substituted indoles and quinolines from 2-vinylanilines and alkynoates through C-C bond cleavage is developed. With these general methods, 2-substituted indoles and quinolines can be accessed via tandem Michael addition and cyclization with no requirement of oxidant. This strategy not only provides a method for the synthesis C2-substituted indoles in good yields through the simultaneous cleavage of C=C and C=C bonds under metal-free conditions but also provides a simple method for the generation of the C2-substituted quinolines in moderate yields via Pd-catalyzed C=C bond cleavage.
An efficient route to quinoline-2-carboxylates via a rhodium-catalyzed oxidative [5+1] annulation of 2-vinylanilines with α-diazocarbonyl compounds
Wang, Cong,Ding, Qiuping,Zheng, Qiang,Bao, Ping,Peng, Yiyuan
, p. 348 - 353 (2017/12/11)
A novel rhodium-catalyzed oxidative [5 + 1] annulation of 2-vinylanilines with α-diazocarbonyl compounds for the construction of quinoline-2-carboxylate derivatives has been developed. A series of functional groups such as methyl, methoxy, fluoro, chloro, bromo, cyano, and even thienyl substituents were tolerated well. This methodology has the potential for use in the pharmaceutical industry.
Method for synthesizing quinoline derivative
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Paragraph 0025; 0026; 0027; 0028; 0029, (2017/02/28)
The invention provides a method for synthesizing a quinoline derivative. Aromatic amine, electrophilic alkyne and alkyne are sequentially added into a reaction vessel according to the molar ratio of 1:1:(1.2-4), solvent is added according to the proportion that 2-4 mL of solvent is added into 1 mmol of aromatic amine, then catalyst silver trifluoromethanesulfonate (AgOTf) with the molar weight being 0.8-5% that of aromatic amine and additive trifluoromethanesulfonic acid (HOTf) with the molar weight being 1.8-10% that of aromatic amine are added, reaction is conducted for 8-24 h at 100-120 DEG C in oil bath, the product is cooled to room temperature, water is added, the product is extracted three times with ethyl acetate, organic layers are combined, decompressive condensing is conducted, the product is subjected to column chromatography purification, and the product, namely the quinoline derivative, is obtained. The quinoline derivative has the advantages that reaction substrates are low in price, the yield is high, selectivity is good, separation and purification are easy, pollution is little, and steps are simple.
Optimized palladium-based approaches to analogues of PK 11195
Guillou, Sandrine,Janin, Yves L.
experimental part, p. 1377 - 1384 (2009/04/07)
(Chemical Equation Presented) The peripheral-type benzodiazepine receptor ligands such as PK 11195 and Ro 5-4864 were found more than twenty years ago in the course of research on neurobiology. These ligands were instrumental in pointing out an involvement of the peripheral-type benzodiazepine receptor (PBR) in apoptosis processes. With in mind an improvement of the solubility of PK 11195 in biological media, we report here improved reaction conditions for the palladium-based arylation reaction of alkyl 1-bromoisoquinoline-3-carboxylates and its ethyl 4-bromoquinoline-2-carboxylate isomer. The use of [1,1′-bis(diphenylphosphino) ferrocene] dichloropalladium as a precatalyst enabled a much improved preparation of an array of the 1-arylisoquinoline-3- carboxylates as well as 4-arylquinoline-3-carboxylates. This work should pave the way for the design of chemical probes aiming at the elucidation of the PBR biological role(s).
Skraup-Doebner-Von Miller quinoline synthesis revisited: Reversal of the regiochemistry for γ-aryl-β,γ-unsaturated α-ketoesters
Wu, Yan-Chao,Liu, Li,Li, Hui-Jing,Wang, Dong,Chen, Yong-Jun
, p. 6592 - 6595 (2007/10/03)
A reversal of the standard regiochemistry of the Skraup-Doebner-Von Miller quinoline synthesis was observed when anilines were condensed with γ-aryl-β,γ-unsaturated α-ketoesters in refluxing TFA. The reaction is proposed to involve 1,2-addition of the ani
