826-81-3Relevant articles and documents
Nickel-Catalyzed Dehydrogenation of N-Heterocycles Using Molecular Oxygen
Banerjee, Debasis,Bera, Atanu,Bera, Sourajit
supporting information, (2020/09/02)
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.
Study on Relationship Between Fluorescence Properties and Structure of Substituted 8-Hydroxyquinoline Zinc Complexes
Jianbo, He,Tingting, Zhou,Yongjing, Cao,Yuanyuan, Zhang,Weiqing, Yang,Menglin, Ma
, p. 1121 - 1126 (2018/08/17)
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.
Method of preparing 8-hydroxy-2-methylquinoline by utilizing chlorquinaldol waste residues
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Paragraph 0026-0027; 0029-0030; 0032-0033; 0034-0036; 0038-0, (2018/09/11)
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.
Microwave-enhanced Friedl?nder synthesis for the rapid assembly of halogenated quinolines with antibacterial and biofilm eradication activities against drug resistant and tolerant bacteria
Garrison, Aaron T.,Abouelhassan, Yasmeen,Yang, Hongfen,Yousaf, Hussain H.,Nguyen, Tho J.,Huigens, Robert W.III.
supporting information, p. 720 - 724 (2017/04/27)
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.
Assembly of Diversely Substituted Quinolines via Aerobic Oxidative Aromatization from Simple Alcohols and Anilines
Li, Jixing,Zhang, Jinlong,Yang, Huameng,Jiang, Gaoxi
supporting information, p. 3284 - 3290 (2017/03/23)
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.
Development of a novel sulfonate ester-based prodrug strategy
Hanaya, Kengo,Yoshioka, Shohei,Ariyasu, Shinya,Aoki, Shin,Shoji, Mitsuru,Sugai, Takeshi
supporting information, p. 545 - 550 (2016/01/09)
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.
Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions
Xia, Shanghua,Gan, Lu,Wang, Kailiang,Li, Zheng,Ma, Dawei
supporting information, p. 13493 - 13496 (2016/10/31)
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).
Quinolines synthesis by reacting 1,3-butanediol with anilines in the presence of iron catalysts
Khusnutdinov,Bayguzina,Aminov
, p. 1613 - 1618 (2016/08/26)
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.
Quinoline Synthesis by the Reaction of Anilines with 1,2-diols Catalyzed by Iron Compounds
Khusnutdinov, Ravil,Bayguzina, Alfiya,Aminov, Rishat,Dzhemilev, Usein
supporting information, p. 1022 - 1029 (2016/07/28)
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.
Discovery of quinoline small molecules with potent dispersal activity against methicillin-resistant Staphylococcus aureus and Staphylococcus epidermidis biofilms using a scaffold hopping strategy
Abouelhassan, Yasmeen,Garrison, Aaron T.,Burch, Gena M.,Wong, Wilson,Norwood, Verrill M.,Huigens, Robert W.
, p. 5076 - 5080 (2014/12/11)
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.
