- Nonreductive deiodination of ortho-iodo-hydroxylated arenes using tertiary amines
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A convenient and nonreductive deiodination is reported for the ortho-iodo-hydroxylated arenes inch ding derivatives of quinolinol, phenol, and naphthol. Tertiary amines pyridine, triethylamine, and N-methylmorpholine in the presence of water initiated deiodination of ortho-iodo-hydroxylated arenes without affecting para-iodine and other reduction-susceptible groups. This reported method also works efficiently for polyiodinated systems. Simplicity, short reaction times, and absence of reducing catalyst are features of this method.
- Talekar, Rahul Subhash,Chen, Grace Shiahuy,Lai, Shin-Yu,Chern, Ji-Wang
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- Glycosylated copper(ii) ionophores as prodrugs for β-glucosidase activation in targeted cancer therapy
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8-Hydroxyquinoline derivatives are metal-binding compounds that have recently attracted interest as therapeutic agents for cancer therapy. In this scenario, we designed and synthesized three new glucoconjugates, 5,7-dichloro-8-quinolinyl-β-d-glucopyranoside, 5-chloro-8-quinolinyl- β-d-glucopyranoside and 2-methyl-8-quinolinyl-β-d-glucopyranoside and investigated their biological properties in comparison to the parent 8-hydroxyquinoline derivatives in the presence of Cu2+. In vitro data show that 2 out of 3 glycosylated compounds possess a pharmacologically- relevant antiproliferative activity against tumor cells, similar to that of their parent compounds; this activity is associated with a relevant triggering of apoptosis. The pharmacological profile of the glucoconjugates depends on the cellular enzymatic β-glucosidase activity, as demonstrated by the inhibition of antiproliferative activity in the presence of the 2,5-dideoxy-2,5-imino-d-mannitol. The Royal Society of Chemistry 2013.
- Oliveri, Valentina,Viale, Maurizio,Caron, Giulia,Aiello, Cinzia,Gangemi, Rosaria,Vecchio, Graziella
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- Study on Relationship Between Fluorescence Properties and Structure of Substituted 8-Hydroxyquinoline Zinc Complexes
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Organic light-emitting diodes (OLEDs) produced from 8-hydroxyquinoline metal complexes play a vital role in modern electroluminescent devices. In this manuscript, a series of 8-hydroxyquinoline derivatives were synthesized by different methods and their corresponding zinc metal complexes were prepared. The UV and fluorescence properties of the complexes were measured aiming to understand the effect of substituents at the quinoline ring on the fluorescence properties of the complexes. When the C-5 of 8-hydroxyquinoline was replaced by halogen group, the fluorescence emission wavelengths had been red-shifted, at the same time, blue-shifted of fluorescence emission wavelength was observed when the C-5 position of 8-hydroxyquinoline was substituted by electron-withdrawing group. When the C-4 position of 8-hydroxyquinolie was substituted by methyl or the C-5 position was substituted by sulfonic acid group, the corresponding zinc complexes had higher fluorescence intensity than 8-hydroxyquinolie zinc.
- Jianbo, He,Tingting, Zhou,Yongjing, Cao,Yuanyuan, Zhang,Weiqing, Yang,Menglin, Ma
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p. 1121 - 1126
(2018/08/17)
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- Preparation method of 5-chloro-8-hydroxyquinoline
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The invention discloses a preparation method of 5-chloro-8-hydroxyquinoline, aiming at solving the problems that when the 5-chloro-8-hydroxyquinoline is prepared by using 4-chloro-2-aminophenol, 4-chloro-2-nitrophenol and glycerol as raw materials and adopting a Skraup method in a loop closing way at present, sulfuric acid reacts violently with the glycerol in a process of dropwise adding the sulfuric acid so as to produce a large amount of acrolein, the acrolein self-polymerizes into tar, the tar is not only difficult to remove during the post-treatment of the product, but also reduces the reaction yield, the reaction process is difficult to control, and a great deal of waste acid is produced. According to the preparation method, hydrochloric acid is used as a solvent and the acrolein istaken as a loop closing raw material, so that the step of producing the acrolein by using the sulfuric acid and the glycerol is avoided, the generation of the tar is effectively reduced, and the heatrelease state of the reaction is controlled; furthermore, the problem that impurities are produced due to a sulfonation reaction of the product can be avoided, the product yield and safety are improved, the reaction is easy to control, and industrialization is easily realized; therefore, the preparation method has a higher application value.
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Paragraph 0040; 0041; 0049; 0051; 0053; 0055
(2018/07/15)
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- A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines
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An operationally simple and metal-free protocol for geometrically inaccessible C5-H halogenation of a range of 8-substituted quinoline derivatives has been established. The reaction proceeds under air, with inexpensive and atom economical trihaloisocyanuric acid as a halogen source (only 0.36 equiv.), at room temperature. Exceptionally high generality with respect to quinoline is observed, and in most instances, the reaction proceeded with complete regioselectivity. Quinoline with a variety of substituents at the 8-position gave, exclusively, the C5-halogenated product in good to excellent yields. Phosphoramidates, tertiary amides, N-alkyl/N,N-dialkyl, and urea derivatives of quinolin-8-amine as well as alkoxy quinolines were halogenated at the C5-position via remote functionalization for the first time. This methodology provides a highly economical route to halogenated quinolines with excellent functional group tolerance, thus providing a good complement to existing remote functionalization methods of quinolin-8-amide derivatives and broadening the field of remote functionalization. The utility of the method is further showcased through the synthesis of several compounds of biological and pharmaceutical interest.
- Motati, Damoder Reddy,Uredi, Dilipkumar,Watkins, E. Blake
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p. 1782 - 1788
(2018/02/23)
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- Quinoline synthesis by improved Skraup-Doebner-Von Miller reactions utilizing acrolein diethyl acetal
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A robust synthetic method has been developed as an improvement to the venerable Skraup-Doebner-Von Miller reaction providing access to various quinoline products. The straightforward procedure utilizes acrolein diethyl acetal as a three-carbon annulation partner with aniline substrates in a monophasic, organic solvent-free reaction medium. Differentially substituted aniline precursors were found to be compatible with the reaction conditions and the corresponding quinoline products are isolated in moderate to good yields.
- Ramann, Ginelle A.,Cowen, Bryan J.
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supporting information
p. 6436 - 6439
(2015/11/16)
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- Synthesis of ortho-alkoxy-aryl carboxamides via alladium-catalyzed aminocarbonylation
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Various aryl carboxamides with alkoxy substituents at the ortho-position, applicable as direct intermediates toward novel ligands, were synthesised via aminocarbonylation of aryl-iodides (2-iodoanisole, 5-chloro-7-iodo-8-methoxy- quinoline, and 5-chloro-7-iodo-8-benzyloxy-quinoline) in the presence of in situ generated palladium(0) catalysts. Simple primary and secondary amines as well as aminoacid esters were used as N-nucleophiles. The optimization of the reaction conditions allowed the preferential formation of carboxamides or ketocarboxamides by simple or double carbon monoxide insertion, respectively. A strong dependence of the chemoselectivity on carbon monoxide pressure was observed. Copyright Taylor & Francis Group, LLC.
- Takacs, Attila,Abreu, Artur R.,Peixoto, Andreia F.,Pereira, Mariette,Kollar, Laszlo
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p. 1534 - 1548
(2009/10/17)
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- Pyridine hydrochloride: A new reagent for the synthesis of o-chloro hydroxy derivatives in pyridine and quinoline series
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Pyridine hydrochloride has been widely used in the cleavage of ethers. It is shown herein that his reagent is also efficient for the synthesis of chloro compounds starting from the corresponding bromo derivatives in π-deficient series such as pyridine and quinoline. Thus, for example, 7-bromo-8-hydroxyquinoline was almost quantitatively converted into 7-chloro-8-hydroxyquinoline. The scope of the reaction has been studied.
- Mongin, Florence,Mongin, Olivier,Trecourt, Francois,Godard, Alain,Queguiner, Guy
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p. 6695 - 6698
(2007/10/03)
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- Hydroformylation of olefins using azoxy-dentated ligands
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At a temperature in the range 100° C to 225° C the destructive dissociation of cobalt carbonyl compounds to cobalt metal and residue is inhibited by the action of one or more azoxy-dentated chelation ligands.
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