- Nickel-Catalyzed Dehydrogenation of N-Heterocycles Using Molecular Oxygen
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Herein, an efficient and selective nickel-catalyzed dehydrogenation of five- and six-membered N-heterocycles is presented. The transformation occurs in the presence of alkyl, alkoxy, chloro, free hydroxyl and primary amine, internal and terminal olefin, trifluoromethyl, and ester functional groups. Synthesis of an important ligand and the antimalarial drug quinine is demonstrated. Mechanistic studies revealed that the cyclic imine serves as the key intermediate for this stepwise transformation.
- Banerjee, Debasis,Bera, Atanu,Bera, Sourajit
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supporting information
(2020/09/02)
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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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- Method of preparing 8-hydroxy-2-methylquinoline by utilizing chlorquinaldol waste residues
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The invention belongs to the technical field of organic waste residue recovery and particularly relates to a method of preparing 8-hydroxy-2-methylquinoline by utilizing chlorquinaldol waste residues.The method comprises the following steps of in the presence of an acid binding agent, utilizing a hydrogenation catalyst to catalyze the chlorquinaldol waste residues, filtering the chlorquinaldol waste residues after catalytic hydrogenation, keeping a solid, performing dissolution with an acid liquid, regulating a pH value of a solution, then performing extraction, keeping an organic phase, andperforming drying and distillation to prepare the 8-hydroxy-2-methylquinoline. For the method provided by the invention, by using palladium-carbon hydroxide as the high-activity hydrogenation catalyst, deficiency of catalysts such as palladium on carbon, raney nickel and platinum on carbon to the reaction activity of a chlorinated product on a conjugate ring and harsh reaction conditions of high temperature, high pressure and the like are avoided, so that reaction is liable to control, the production period is short, and industrialization is liable.
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Paragraph 0026-0027; 0029-0030; 0032-0033; 0034-0036; 0038-0
(2018/09/11)
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- Microwave-enhanced Friedl?nder synthesis for the rapid assembly of halogenated quinolines with antibacterial and biofilm eradication activities against drug resistant and tolerant bacteria
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Herein, we disclose the development of a catalyst- and protecting-group-free microwave-enhanced Friedl?nder synthesis which permits the single-step, convergent assembly of diverse 8-hydroxyquinolines with greatly improved reaction yields over traditional oil bath heating (increased from 34% to 72%). This rapid synthesis permitted the discovery of novel biofilm-eradicating halogenated quinolines (MBECs = 1.0-23.5 μM) active against MRSA, MRSE, and VRE. These small molecules exhibit activity through mechanisms independent of membrane lysis, further demonstrating their potential as a clinically useful treatment option against persistent biofilm-associated infections.
- Garrison, Aaron T.,Abouelhassan, Yasmeen,Yang, Hongfen,Yousaf, Hussain H.,Nguyen, Tho J.,Huigens, Robert W.III.
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p. 720 - 724
(2017/04/27)
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- Assembly of Diversely Substituted Quinolines via Aerobic Oxidative Aromatization from Simple Alcohols and Anilines
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An aerobic oxidative aromatization of simple aliphatic alcohols and anilines under the Pd(OAc)2/2,4,6-Collidine/Br?nsted acid catalytic system has been established, providing a direct approach for the preparation of diverse substituted quinoline derivatives in high yields with wide functional group tolerance. Practically, the protocol can be easily scaled up to gram-scale and was utilized in the concise formal synthesis of a promising herbicide candidate.
- Li, Jixing,Zhang, Jinlong,Yang, Huameng,Jiang, Gaoxi
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supporting information
p. 3284 - 3290
(2017/03/23)
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- Development of a novel sulfonate ester-based prodrug strategy
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A self-immolative γ-aminopropylsulfonate linker was investigated for use in the development of prodrugs that are reactive to various chemical or biological stimuli. To demonstrate their utility, a leucine-conjugated prodrug of 5-chloroquinolin-8-ol (5-Cl-8-HQ), which is a potent inhibitor against aminopeptidase from Aeromonas proteolytica (AAP), was synthesized. The sulfonate prodrug was considerably stable under physiological conditions, with only enzyme-mediated hydrolysis of leucine triggering the subsequent intramolecular cyclization to simultaneously release 5-Cl-8-HQ and form γ-sultam. It was also confirmed that this γ-aminopropylsulfonate linker was applicable for prodrugs of not only 8-HQ derivatives but also other drugs bearing a phenolic hydroxy group.
- Hanaya, Kengo,Yoshioka, Shohei,Ariyasu, Shinya,Aoki, Shin,Shoji, Mitsuru,Sugai, Takeshi
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supporting information
p. 545 - 550
(2016/01/09)
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- Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions
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The combination of Cu(acac)2 and N,N′-bis(4-hydroxyl-2,6-dimethylphenyl)oxalamide (BHMPO) provides a powerful catalytic system for hydroxylation of (hetero)aryl halides. A wide range of (hetero)aryl chlorides bearing either electron-donating or -withdrawing groups proceeded well at 130 °C, delivering the corresponding phenols and hydroxylated heteroarenes in good to excellent yields. When more reactive (hetero)aryl bromides and iodides were employed, the hydroxylation reactions completed at relatively low temperatures (80 and 60 °C, respectively) at low catalytic loadings (0.5 mol % Cu).
- Xia, Shanghua,Gan, Lu,Wang, Kailiang,Li, Zheng,Ma, Dawei
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supporting information
p. 13493 - 13496
(2016/10/31)
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- Quinolines synthesis by reacting 1,3-butanediol with anilines in the presence of iron catalysts
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2-, 4-, 6-, 7-, and 8-substituted quinolines were synthesized in 78–95% yield by the reaction of 1,3- butanediol with anilines in the presence of iron catalysts in carbon tetrachloride.
- Khusnutdinov,Bayguzina,Aminov
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p. 1613 - 1618
(2016/08/26)
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- Quinoline Synthesis by the Reaction of Anilines with 1,2-diols Catalyzed by Iron Compounds
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The synthesis of quinoline derivatives by cyclocondensation of anilines with 1,2-ethanediol, 1,2-propanediol, and 1,2-butanediol in the presence of iron-containing catalysts was performed for the first time.
- Khusnutdinov, Ravil,Bayguzina, Alfiya,Aminov, Rishat,Dzhemilev, Usein
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supporting information
p. 1022 - 1029
(2016/07/28)
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- Discovery of quinoline small molecules with potent dispersal activity against methicillin-resistant Staphylococcus aureus and Staphylococcus epidermidis biofilms using a scaffold hopping strategy
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Staphylococcus aureus and Staphylococcus epidermidis are recognized as the most frequent cause of biofilm-associated nosocomial and indwelling medical device infections. Biofilm-associated infections are known to be highly resistant to our current arsenal of clinically used antibiotics and antibacterial agents. To exacerbate this problem, no therapeutic option exists that targets biofilm-dependent machinery critical to Staphylococcal biofilm formation and maintenance. Here, we describe the discovery of a series of quinoline small molecules that demonstrate potent biofilm dispersal activity against methicillin-resistant S. aureus and S. epidermidis using a scaffold hopping strategy. This interesting class of quinolines also has select synthetic analogues that demonstrate potent antibacterial activity and biofilm inhibition against S. aureus and S. epidermidis.
- Abouelhassan, Yasmeen,Garrison, Aaron T.,Burch, Gena M.,Wong, Wilson,Norwood, Verrill M.,Huigens, Robert W.
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p. 5076 - 5080
(2014/12/11)
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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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supporting information
p. 2023 - 2034
(2013/03/14)
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- Photochemical cleavage reactions of 8-quinolinyl sulfonates in aqueous solution
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Photochemical cleavage reactions of 8-quinolinyl benzenesulfonate derivatives and related sulfonates in aqueous solutions are reported. The 8-quinolinyl benzenesulfonates undergo photolysis upon photoirradiation at 300-330 nm to give the corresponding 8-quinolinols and benzenesulfonic acids with the production of only negligible amounts of byproducts. The effects of substituent groups of the 8-quinolinyl moiety and the benzene ring on the photolysis reactions were examined. Based on steady-state mechanistic studies using a triplet sensitizer, a triplet quencher, and electron donors, it was suggested that the photolysis proceeds mainly via the homolytic cleavage of S-O bonds in the excited triplet state.
- Kageyama, Yoshiyuki,Ohshima, Ryosuke,Sakurama, Kazusa,Fujiwara, Yoshihisa,Tanimoto, Yoshifumi,Yamada, Yasuyuki,Aoki, Shin
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experimental part
p. 1257 - 1266
(2010/05/02)
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- A facile synthesis of 2-methylquinolines via Pd-catalyzed aza-Wacker oxidative cyclization
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(Chemical Equation Presented) A novel Pd-catalyzed Wacker-type oxidative cyclization under air is described. By using this cyclization, a series of 2-methylquinolines are readily prepared with good yields under mild conditions.
- Zhang, Zuhui,Tan, Jiajing,Wang, Zhiyong
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p. 173 - 175
(2008/09/18)
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- Synthesis of quinaldines and lepidines by a Doebner-Miller reaction under thermal and microwave irradiation conditions using phosphotungstic acid
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A simple and efficient method has been developed for the synthesis of quinaldines and lepidines by a one-pot reaction of anilines with crotonaldehyde or methyl vinyl ketone using phosphotungstic acid, a Keggins-type heteropoly acid, under both thermal and microwave irradiation conditions.
- Sivaprasad, Ganesabaskaran,Rajesh, Rengasamy,Perumal, Paramasivan T.
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p. 1783 - 1785
(2007/10/03)
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- Regioselective synthesis of quinolin-8-ols and 1,2,3,4- tetrahydroquinolin-8-ols by the cyclization of 2-(3-hydroxyphenyl)ethyl ketone 0-2,4-dinitrophenyloximes
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Cyclization of 2-(3-hydroxyphenyl)ethyl ketone 0-2,4- dinitrophenyloximes proceeds on the oxime nitrogen atom by the treatment with NaH and then with 2,3-dichloro-5,6-dicyano-p-benzoquinone and acetic acid to yield quinolin-8-ols regioselectively. The reaction in the presence of Na[BH3(CN)] affords 1,2,3,4-tetrahydroquinolin-8-ols. The present cyclization proceeds via alkylideneaminyl radical intermediates generated by the single electron transfer between 3-hydroxyphenyl and 2,4-dinitrophenyl moieties.
- Uchiyama, Katsuya
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p. 2945 - 2955
(2007/10/03)
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- Synthesis of 8-hydroxyquinolines by the cyclization of m-hydroxyphenethyl ketone O-2,4-dinitrophenyloximes
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8-Hydroxyquinolines are synthesized from O-2,4-dinitrophenyloximes of m-hydroxyphenethyl ketones by the treatment with sodium hydride, and then with 2,3-dichloro4,5-dicyano-p-benzoquinone (DDQ).
- Uchiyama, Katsuya,Hayashi, Yujiro,Narasaka, Koichi
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p. 445 - 446
(2007/10/03)
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- Synthesis of mono-and dialkylsubstituted 1,10-Phenanthrolines
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Starting from o-anisidine, alkylated 8-hydroxyquinolines 2 and 8-aminoquinolines 3 were obtained. From the latter, dialkylsubstituted 1,10-phenanthrolines 5 have been prepared in good yields. Reaction of unsubstituted 8-aminoquinoline under the same conditions, yielded monoalkylated 1,10-phenanthrolines 4.
- Belser, Peter,Bernhard, Stefan,Guerig, Urs
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p. 2937 - 2944
(2007/10/03)
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- AMINODEMETHOXYLATION IN QUINOLINES AND NAPHTHALENES
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Substitution of the methoxy group in inactivated aromatic and heterocyclic substrates by alkylamines takes place by bimolecular nucleophilic substitution at a saturated carbon atom with the formation of phenolic intermediates and subsequent substitution of the hydroxyl group by the alkylamino group.In the temperature range between 150 and 200 deg C in the presence of ammonium chloride the substitution of the hydroxy group in 1- and 2-hydroxynaphthalenes and 6-, 7-, and 8-hydroxyquinolines, and of the methoxy group in 1- and 2-methoxynaphthalenes and 6-, 7-, and 8-methoxyquinolines takes place almost quantitatively.
- Terenin, V. I.,Gerasimenko, V. A.,Nikishova, N. G.,Kurts, A. L.,Afanas'eva, T. A.,Bundel', Yu. G.
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p. 1890 - 1896
(2007/10/02)
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- Dissociation of μ-Oxo-bis and μ-Oxo-bis in Chlorobenzene
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Dissociation of dimeric vanadium(V) complexes with 8-quinolinol(Hox) and 4-isopropyltropolone(Hipt), V2O3(ox)4 and V2O3(ipt)4, in organic solvents was studied spectrophotometrically.The equilibrium is found to be V2O3L4 + H2O 2VO2L + 2HL with the foll
- Yuchi, Akio,Muranaka, Hiroshi,Yamada, Shinkichi,Tanaka, Motoharu
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p. 1560 - 1563
(2007/10/02)
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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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