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Zuzana Kozubková Michal Rouchal Marek Nečas Robert Vícha 《Helvetica chimica acta》2012,95(6):1003-1017
2,3,4‐Trisubstituted quinolines, substituted with adamantan‐1‐yl or (adamantan‐1‐yl)methyl in the 4‐position, were prepared from the corresponding admantan‐1‐yl 2‐aminophenyl ketones or admantan‐1‐ylmethyl 2‐aminophenyl ketones and ketones with an α‐CH2 group. These reactions were carried out under neat conditions or in toluene, and the products were obtained in moderate‐to‐excellent yields. The scope and limitations of the examined procedures are discussed. All new compounds are fully characterized by IR and NMR spectroscopy and mass spectrometry. The molecular structures of five new quinolines, obtained via single‐crystal X‐ray diffraction analyses, are discussed. 相似文献
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A novel preparation of 4‐phenylquinoline derivatives through acid‐catalyzed Friedländer reaction in ionic liquid ([bmim][BF4]) is described. The preparative procedure presented in this paper is operationally simple and environmentally benign. The reaction media and the catalyst used can be recovered and reused for at least four times without loss in the catalytic activity. 相似文献
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《应用有机金属化学》2017,31(2)
A magnetic nanocatalyst of Fe3O4@SiO2/ZnCl2 was prepared by supporting ZnCl2 on silica‐coated magnetic nanoparticles of Fe3O4. This recoverable catalyst was used for the synthesis of quinolines via Friedländer synthesis from 2‐aminoaryl ketones and α‐methylene ketones under solvent‐free condition. The prepared catalyst was characterized by FT‐IR, TEM, SEM, XRD, EDX, ICP‐OES, VSM and BET. It was found that Fe3O4@SiO2/ZnCl2 showed higher catalytic activity than homogenous ZnCl2, and could be reused several times without significant loss of activity. 相似文献
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The synthesis of substituted quinolines can be easily and greenly accomplished by the direct reaction between the corresponding aminoalcohol and ketone using PEG‐400 as reaction medium in the presence of a base, without any transition‐metal catalyst. 相似文献
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A mild, eco‐friendly and efficient route for the synthesis of quinolines and polycyclic quinolines via Friedländer annulation using cyanuric chloride as a catalyst under aqueous conditions is described. 相似文献
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Saravanakumar Elangovan Dr. Jean‐Baptiste Sortais Prof. Dr. Matthias Beller Prof. Dr. Christophe Darcel 《Angewandte Chemie (International ed. in English)》2015,54(48):14483-14486
A general and benign iron‐catalyzed α‐alkylation reaction of ketones with primary alcohols has been developed. The key to success of the reaction is the use of a Knölker‐type complex as catalyst (2 mol %) in the presence of Cs2CO3 as base (10 mol %) under hydrogen‐borrowing conditions. Using 2‐aminobenzyl alcohol as alkylation reagent allows for the “green” synthesis of quinoline derivatives. 相似文献
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Andrzej Danel Ewa Gondek Mateusz Kucharek Pawe Szlachcic Arkadiusz Gut 《Molecules (Basel, Switzerland)》2022,27(9)
This paper summarises a little over 100 years of research on the synthesis and the photophysical and biological properties of 1H-pyrazolo[3,4-b]quinolines that was published in the years 1911–2021. The main methods of synthesis are described, which include Friedländer condensation, synthesis from anthranilic acid derivatives, multicomponent synthesis and others. The use of this class of compounds as potential fluorescent sensors and biologically active compounds is shown. This review intends to summarize the abovementioned aspects of 1H-pyrazolo[3,4-b]quinoline chemistry. Some of the results that are presented in this publication come from the laboratories of the authors of this review. 相似文献
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scar M. Bautista‐Aguilera Lhassane Ismaili Isabel Iriepa Daniel Diez‐Iriepa Fakher Chabchoub Jos Marco‐Contelles Marta Prez 《Chemical record (New York, N.Y.)》2021,21(1):162-174
Herein we have reviewed our recent developments for the identification of new tacrine analogues for Alzheimer's disease (AD) therapy. Tacrine, the first cholinesterase inhibitor approved for AD treatment, did not stop the progression of AD, producing only some cognitive improvements, but exhibited secondary effects mainly due to its hepatotoxicity. Thus, the drug was withdrawn from the clinics administration. Since then, many publications have described non‐hepatotoxic tacrines, and in addition, important efforts have been made to design multitarget tacrines by combining their cholinesterase inhibition profile with the modulation of other biological targets involved in AD. 相似文献
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A mild and efficient route for the synthesis of quinolines and polycyclic quinolines utilizing Gadolinium triflate (Gd(OTf)3) as a novel catalyst via Friedländer annulation in ionic liquid 1‐n‐butyl‐3‐methyl‐imidazolium hexafluorophosphate [Bmim][PF6] under mild conditions was described. 相似文献
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The preparation of a new class of tricyclic models 1 based on a Friedländer reaction between chiral piperidine-2,4-diones 2 and azomethine 3 is reported. Alkylation of the lactam allowed to install various pendant arms on the chiral cyclic inducer. The so-obtained mimics 1a,d,f,g,h,k were involved in the reduction of methyl benzoylformate to furnish methyl mandelate in 4-87% ee (R). The presence of a coordinating pendant arm proved to be essential to reach optimum results in terms of enantioinduction. Asymmetric reduction of 2-benzoylpyridine with mimics 1d,f,g produced α-phenyl-2-pyridinemethanol in 30-84% ee (R). 相似文献
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In the context of formation of camptothecins substituted by a carbonyl function on position 5 of cycle C, synthesis of a new keto tetrahydroindolizine was realized. This compound was obtained from the reaction of Bredereck's reagent with an indolizine derived from pyroglutamic acid. That yielded a dimethylaminovinyl group whose NaIO4 oxidation gave a ketone. The indolizinone obtained was reacted in Friedlander condition to give the ABCD ring scaffold of camptothecins substituted by a methoxycarbonyl group on the 5-position. It was also shown that, if it is desired, a 5-carboxamide group does not need to be introduced at the beginning of the synthesis sequence. 相似文献
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An efficient and stereoselective approach to the synthesis of coenzyme Q10 is described (Scheme). The MeOCH2‐protected p‐hydroquinone 4 containing the C5 (E)‐allyl (tert‐butyl)dimethylsilyl ether moiety was obtained via a halogen–lithium exchange of the MeOCH2‐proctected 2‐bromo‐5,6‐dimethoxy‐3‐methylhydroquinone 2 and subsequent addition to (E)‐(tBuMe2Si)‐OCH2C(Me)=CHCH2Br ( 3 ). The reductive desulfonylation of compound 8 , obtained from 4 via 5 – 7 , was successfully carried out by employing Li/EtNH2. 相似文献
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The Friedländer synthesis offers efficient access to substituted quinolines from 2-aminobenzaldehydes and activated ketones in the presence of a base. The disadvantage of this procedure lies in the fact that relatively few 2-aminobenzaldehyde derivatives are readily available. To overcome this problem, we report a modification of this process involving the in situ reduction of 2-nitrobenzaldehydes with Fe/AcOH in the presence of active methylene compounds (AMCs) to produce substituted quinolines in high yields. The conditions are mild enough to tolerate a wide range of functionality in both reacting partners and promote reactions not only with phenyl and benzyl ketones, but also with β-keto-esters, β-keto-nitriles, β-keto-sulfones and β-diketones. The reaction of 2-nitroaromatic ketones with unsymmetrical AMCs is less reliable, giving a competitive formation of substituted quinolin-2(1H)-ones from the cyclization of the Z Knoevenagel intermediate which appears to be favored when certain large groups are adjacent to the AMC ketone carbonyl. 相似文献
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Shuang Pan Luze He Juan Peng Feng Qiu Zhiqun Lin 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2016,128(30):8912-8912
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The Schmidt and Beckmann rearrangement of 3,4-dihydro-4,4-dimethyl-1(2H)-naphthalenones bearing oxygenated groups at the 5,8-positions, and some of their oximes are reported. Depending upon the structure of the substrates and the reaction conditions 4,5-dihydro-3H-naphth[1,8-cd]isoxazol, benzazepin-2-one and 5,6-dihydro-7H-tetrazolo[1,5-a][2]benzazepine derivatives were generated. 相似文献