- Synthesis of substituted quinolines via B(C6F5)3-catalyzed aniline-aldehyde-pyruvate oxidative annulation
-
A metal-free method to construct quinoline derivatives via B(C6F5)3-catalyzed cyclization of anilines with aldehyde derivatives and pyruvates is described. This three-component cascade reaction provides an efficient approa
- Ling, Fei,Chen, Jiachen,Xie, Zhen,Hou, Huacui,Pan, Zhentao,Feng, Cong,Shen, Haiwei,Zhong, Weihui
-
-
Read Online
- Palladium-Catalyzed Three-Component Cascade Reaction of Nitriles: Synthesis of 2-Arylquinoline-4-carboxylates
-
A new method for converting easy availability starting materials 2-(2-oxoindolin-3-yl)acetonitrile, arylboronic acids, and alcohols into 2-arylquinoline-4-carboxylates is reported. The procedure involves a three-component addition/ring expansion/esterification reaction in the presence of Pd(II) catalyst with high functional group tolerance under mild conditions. In addition, the photophysical properties of the resulting product were investigated and exhibited excellent polarity-sensitive fluorescence properties and AIE property.
- Zhao, Zhiwei,Zeng, Ge,Chen, Yinan,Zheng, Jinming,Chen, Zhongyan,Shao, Yinlin,Zhang, Fangjun,Chen, Jiuxi,Li, Renhao
-
p. 7955 - 7960
(2021/10/20)
-
- Ethyl lactate-involved three-component dehydrogenative reactions: Biomass feedstock in diversity-oriented quinoline synthesis
-
Three-component reactions of ethyl/methyl lactate, anilines and aldehydes providing quinolines have been developed via simple iron(iii) chloride catalysis without using an additional organic medium or external oxidant. This three-component protocol shows
- Wan, Jie-Ping,Yang, Lu
-
supporting information
p. 3074 - 3078
(2020/06/25)
-
- Selective Methylation of Arenes: A Radical C?H Functionalization/Cross-Coupling Sequence
-
A selective, nonchelation-assisted methylation of arenes has been developed. The overall transformation, which combines a C?H functionalization reaction with a nickel-catalyzed cross-coupling, offers rapid access to methylated arenes with high para selectivity. The reaction is amenable to late-stage methylation of small-molecule pharmaceuticals.
- Serpier, Fabien,Pan, Fei,Ham, Won Seok,Jacq, Jér?me,Genicot, Christophe,Ritter, Tobias
-
supporting information
p. 10697 - 10701
(2018/07/31)
-
- Triple zirconocene/br?nsted acid/CuO cooperative and relay catalysis system for tandem Mannich addition/C-C formative cyclization/oxidation
-
A new triple cooperative and relay catalysis system featuring the Mannich addition followed by C-C construction and oxydehydrogenation is described. The zirconocene dichloride and trimellitic acid synergic catalysis triggered the Mannich addition and C-C bond construction reactions, while CuO allowed relay catalysis for oxydehydrogenation. This novel strategy demonstrated superior activity for the synthesis of substituted quinolines from commercially available anilines, aldehydes and ketones. The corresponding substituted quinolines were synthesized with 32 examples in 90-96% yields under mild reaction conditions. A novel zirconocene-Br?nsted acid complex, generated in situ and acting as an active catalyst, was validated from the mechanistic studies.
- Luo, Yanlong,Sun, Huaming,Zhang, Weiqiang,Wang, Xiu,Xu, Shan,Zhang, Guofang,Jian, Yajun,Gao, Ziwei
-
p. 28616 - 28625
(2017/07/10)
-
- Method for efficiently preparing polysubstituted quinoline by synergy of copper oxide and zirconocene double-acid system
-
The invention discloses a method for efficiently preparing polysubstituted quinoline by synergy of copper oxide and a zirconocene double-acid system. According to the method, a mixed solution of water and isopropyl alcohol is taken as a solvent, a compound formed by biszirconium dichloride and a benzoic acid ligand is taken as a double-acid catalyst, and aromatic amine, aldehyde and ketone are efficiently catalyzed by the double-acid catalyst to be reacted to prepare the polysubstituted quinoline under the synergistic effect of copper oxide. The method is wide in substrate application range, mild in reaction condition, short in time and high in atom economy, the raw materials are low in cost and readily available, the catalyst is stable, low in cost and nontoxic for water and the air, a novel low-cost, green and efficient means is provided for preparation of the polysubstituted quinoline, and the prepared polysubstituted quinoline has a great application potential to preparation of a medicament, a natural product, a luminous material and an organic synthetic intermediate.
- -
-
Paragraph 0015; 0016; 0017; 0018; 0019; 0020
(2017/01/31)
-
- Convergent synthesis and cytotoxicity of novel trifluoromethyl-substituted (1H-pyrazol-1-yl)(quinolin-4-yl) methanones
-
A convergent synthesis of a series of 16 new polysubstituted (5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl)(quinolin-4-yl)methanones, starting from isatin and alky(aryl/heteroaryl) ketones, is described. The diheteroaryl methanones were achieved at yields of up to 95% by a [3?+?2] cyclocondensation reaction involving 4-alkyl(aryl/heteroaryl)-4-methoxy-1,1,1-trifluorobut-3-en-2-ones (by two-step reaction) and 2-alkyl(aryl/heteroaryl)-4-carbohydrazides (by three-step reaction). Subsequently, representative dehydrated heterocyclic derivatives were obtained from the respective 5-hydroxy-2-pyrazoline moieties by classical dehydration reactions, which resulted in the corresponding (5-(trifluoromethyl)-1H-pyrazol-1-yl)(quinolin-4-yl)methanones (three examples) at yields of 69–82%. The subsequent cytotoxicity evaluation showed that compounds with aromatic groups at the 2-position of the quinoline and a methyl moiety at the 3-position of the pyrazole have significant cytotoxicity in human leukocytes at high concentrations (200?μM).
- Bonacorso, Helio G.,Nogara, Pablo A.,Silva, Fernanda D'A.,Rosa, Wilian C.,Wiethan, Carson W.,Zanatta, Nilo,Martins, Marcos A.P.,Rocha, Jo?o B.T.
-
-
- Phosphorescent biscyclometallated iridium(iii) ethylenediamine complexes functionalised with polar ester or carboxylate groups as bioimaging and visualisation reagents
-
We report the synthesis, characterisation and photophysical properties of new phosphorescent biscyclometallated iridium(iii) ethylenediamine (en) complexes functionalised with polar ester or carboxylate groups [Ir(N^C)2(en)]n(X) (n = +1, X = Cl-, HN^C = methyl 4-(2-pyridyl)benzoate Hppy-COOMe (1a), methyl 2-phenyl-4-quinolinecarboxylate Hpq-COOMe (2a); n = -1, X = Li+, HN^C = 4-(2-pyridyl)benzoate Hppy-COO- (1b), 2-phenyl-4-quinolinecarboxylate Hpq-COO- (2b)). In aqueous solutions, the carboxylate complexes 1b and 2b displayed emission quenching (ca. 7 and 74 fold, respectively) and lifetime shortening upon protonation, and their pKa values were determined to be 5.13 and 3.46, respectively. The pq complexes 2a and 2b exhibited hypsochromic shifts in their emission maxima and a significant increase in emission intensity (ca. 84 and 15 fold, respectively) upon nonspecific binding to the protein bovine serum albumin (BSA). Inductively coupled plasma-mass spectroscopy (ICP-MS) and laser-scanning confocal microscopy (LSCM) results revealed that the ester complexes 1a and 2a were efficiently internalised by the human cervix epithelioid carcinoma (HeLa) cells through energy-requiring pathways and subsequently localised in endosomes and mitochondria, respectively. They showed good biocompatibility in the dark, but became significantly cytotoxic upon photoirradiation due to the generation of singlet oxygen. In contrast, in aqueous solutions of physiological pH, the carboxylate complexes 1b and 2b existed as the anionic form and hardly entered cells due to limited membrane permeability, as evidenced by the intense emission surrounding the plasma membrane of the cells. They showed negligible cytotoxicity and the cell viability remained over 95% for an incubation period of 24 hours. In view of the low cytotoxicity and strongly emissive nature of the hydrophilic ppy-COO- complex 1b in an aqueous medium, the potential application of the complex as a visualisation reagent has been demonstrated using zebrafish (Danio rerio) as an animal model. This journal is
- Tang, Tommy Siu-Ming,Leung, Kam-Keung,Louie, Man-Wai,Liu, Hua-Wei,Cheng, Shuk Han,Lo, Kenneth Kam-Wing
-
p. 4945 - 4956
(2015/03/18)
-
- Synthesis of Quinolines by Visible-Light Induced Radical Reaction of Vinyl Azides and α-Carbonyl Benzyl Bromides
-
A visible-light induced radical reaction of vinyl azides and α-carbonyl benzyl bromides was developed, which provides an efficient route to polysubstituted quinolines via a C-C and C-N bond formation sequence.
- Wang, Qile,Huang, Jun,Zhou, Lei
-
p. 2479 - 2484
(2015/08/18)
-
- QUINOLINES DERIVATIVES AS NOVEL ANTICANCER AGENTS
-
The invention provides quinoline derivatives, their manufacture, pharmaceutical compositions containing them, and their use as medicaments. The active compounds of the present invention are useful for the treatment of proliferative neoplastic and nonneoplastic diseases.
- -
-
Page/Page column 101; 102
(2014/10/03)
-
- A multicomponent reaction of acetals for the preparation of quinolines
-
A straightforward, mild, one-pot method has been found for the preparation of quinolines via a multi-component reaction using acetals or cyclic acetals, aromatic amines and alkynes catalysed by Bi(OTf)3. It gives good yields under mild conditions. This approach has been successfully applied for the synthesis of a range of quinolines with a variety of functional groups.
- Zhang, Xue-Lin,Wu, Qin-Pei,Zhang, Qing-Shan
-
p. 677 - 680
(2014/01/17)
-
- Design, synthesis and evaluation of quinoline-based small molecule inhibitor of stat3
-
As STAT3 has been validated as an anticancer target, its inhibitors have been shown to possess therapeutic promise for the treatment of human cancers. To identify novel and selective STAT3 inhibitors, a virtual screening based on the STAT3 SH2 domain was performed and a small molecule, 2-phenylquinoline-4- carboxylic acid (5a), with an inhibition constant Ki value of 17.53 iM to STAT3 was discovered. On this basis, the derivatives of 5a including esters, amides and dimers were synthesized. The bioactivity and inhibitory selectivity of the derivatives were assayed using human breast cancer cell lines, MDA-MB-468 and MCF-7. Among the derivatives, 5c and 9b showed the most potent inhibitory activity with a good selectivity, and also inhibited STAT3 protein level of MDA-MB-468 cells. The results demonstrated a successful application of virtual screening for lead discovery. Compound 9b might be an effective STAT3 inhibitor lead for the further development of antitumor agents.
- Shi, Zhi-Bing,Zhang, Lei,Bin, Zheng-Yang,Cao, Xiang-Rong,Gong, Zhu-Nan,Li, Jian-Xin
-
p. 420 - 426
(2013/07/26)
-
- Synthesis of substituted quinolines by iron-catalyzed oxidative coupling reactions
-
A simple and efficient method has been developed for the synthesis of quinoline derivatives from N-alkyl anilines and alkynes or alkenes by iron-catalyzed oxidative coupling reactions. A variety of substituted quinolines are prepared in good to excellent yields.
- Liu, Peng,Li, Yuxi,Wang, Haiyu,Wang, Zhiming,Hu, Xianming
-
supporting information
p. 6654 - 6656,3
(2012/12/13)
-
- Synthesis of some 2-aryl- and 2,3-diaryl-quinolin-4-carboxylic acid derivatives
-
Eighteen 2-aryl- and 2,3-diaryl-quinolin-4-carboxlic acid derivatives were synthesized. Basically, the synthetic design of these compounds arose from the appropriate disconnections of the target compounds, which revealed pyruvic acid, aromatic amine, and benzaldehyde or phenyl pyruvic acid, aromatic amine, and benzaldehyde as possible logical precursors for 2-aryl- and 2,3-aryl-quinolin-4- carboxylic acids respectively. The purity and identities of the synthesized compounds were elucidated through chromatographic and spectroscopic techniques (ultraviolet, infrared, mass, 1H NMR, and 13C NMR). The prepared derivatives were screened for their antibacterial activity against the standard bacterial organisms B. subtilis, S. aureus, E. coli, and P. vulgaris. 2,3-Diphenyl-6-sulfanilamido-quinolin-4-carboxylic acid showed the highest activity against the four tested organisms.
- Saeed,Elhadi
-
experimental part
p. 1435 - 1443
(2011/06/20)
-
- Studies on novel 2-imidazolidinones and tetrahydropyrimidin-2(1H)-ones as potential TACE inhibitors: Design, synthesis, molecular modeling, and preliminary biological evaluation
-
Compounds belonging to the class of 2-imidazolidinones and tetrahydropyrimidin-2(1H)-ones were synthesized and evaluated for their TACE inhibitory activity. Most of the compounds showed very good TACE inhibitory activity. Docking study clearly indicates importance of the P1′ group of the inhibitor for the TACE inhibitory activity. This work proves that these two classes of molecules could be used as potential leads for the development of TACE inhibitors.
- DasGupta, Shirshendu,Murumkar, Prashant R.,Giridhar, Rajani,Yadav, Mange Ram
-
experimental part
p. 3604 - 3617
(2009/09/30)
-
- Practical and simple synthesis of substituted quinolines by an HCL-DMSO system on a large scale: Remarkable effect of the chloride ion
-
A variety of substituted quinolines are synthesized from imines and enolizable carbonyl compounds under aerobic conditions, in which only water is a byproduct. In DMSO, a catalytic amount of HCl activates carbonyl compounds quite effectively to give the quinolines. A simple and practical procedure is demonstrated on a large scale.
- Tanaka, Shin-Ya,Yasuda, Makoto,Baba, Akio
-
p. 800 - 803
(2007/10/03)
-
- Rapid synthesis of quinoline-4-carboxylic acid derivatives from arylimines and 2-substituted acrylates or acrylamides under indium(III) chloride and microwave activations. Scope and limitations of the reaction
-
Rapid synthesis of quinoline-4-carboxylic acid derivatives has been achieved by reaction of 2-methoxy acrylates or acrylamides with N-arylbenzaldimines in acetonitrile under InCl3 catalysis and microwave irradiation. Isolated yields up to 57% within 3 min have been obtained. The Lewis acid and the microwave activation appeared as crucial parameters for the reaction. The role of indium chloride and ytterbium triflate was specified using 13C NMR data and model theoretical studies. The Royal Society of Chemistry 2005.
- Duvelleroy, Dorothee,Perrio, Cecile,Parisel, Olivier,Lasne, Marie-Claire
-
p. 3794 - 3804
(2007/10/03)
-
- Palladium-catalyzed intramolecular coupling between aryl iodides and allyl moieties via thermal and microwave-assisted conditions
-
Palladium-catalyzed intramolecular cross-coupling reactions between aryl iodides and allyl moieties were successfully demonstrated in the presence of palladium catalyst, tri-o-tolylphosphine, a tertiary amine, and water. Several kinds of trans-2,4-disubst
- Lautens, Mark,Tayama, Eiji,Herse, Christelle
-
-
- Mercury(II) and gold(III) derivatives of 2-phenyl pyridines and 2-phenyl-4-(methylcarboxylato)quinoline
-
ortho-Mercurated derivatives of several substituted 2-phenylpyridines and of 2-phenyl-4-(methylcarboxylato)quinoline have been prepared and characterised. C,N-chelated gold(III) derivatives, [AuCl2(C6H4C5H3RN)] (R = H, 3-Me, 3,5-Me2, 4-Prn, 4-But) are prepared more efficiently by trans-metallation reactions than by direct reaction of AuCl4- with the phenylpyridines. The new gold complexes were characterised spectroscopically and a variety of substitution reactions have been effected. As is usual with unsymmetrical bidentate ligands, the softer donor atom is found trans to the N-donor of the pyridine unit. Crystal-structure determinations are reported for [Au(OAc)(pmpy)(py)]ClO4, [Au(ppy)(dpbt)]BPh4, [Au(ppy)(S2CNMe2)]BPh4 and AuCl(pqcm)2 [Hppy = 2-phenylpyridine, Hpmpy = 2-phenyl-3-methylpyridine, Hpqcm = 2-phenyl-4-(methylcarboxylato)quinoline].
- Parish,Wright, Jonathan P.,Pritchard, Robin G.
-
p. 165 - 176
(2007/10/03)
-
- Formation of 4-Nitro-2-phenylquinoline on Attempted Diazotization of 3-Amino-2-phenylquinoline-4-carboxylic Acid
-
Treatment of 3-amino-2-phenylquinoline-4-carboxylic acid with isoamyl nitrite in acidic dimethylformamide gave 4-nitro-2-phenylquinoline.
- Brown, Roger F. C.,Coulston, Karen J.,Eastwood, Frank W.,Jurss, Craig J.
-
p. 566 - 570
(2007/10/02)
-
- THE REACTION OF IMIDOYL RADICALS WITH MULTIPLE CARBON-CARBON BONDS
-
A general view on the reaction between imidoyl radicals and carbon-carbon double or triple bonds is given; the synthesis of substituted quinolines starting from imines and alkenes is described, pointing out the differences with respect to the analogous reaction performed with alkynes.
- Leardini, Rino,Nanni, Daniele,Tundo, Antonio,Zanardi, Giuseppe
-
p. 637 - 642
(2007/10/02)
-
- Studies on the N-Oxides of ?-Deficient N-Heteroaromatics. XXXVI. Photochemical and Thermal Michael Reactions of Alcohols with Methyl 2-Phenyl-3,1-benzoxazepine-5-carboxylate and Its Derivatives
-
Irradiation (>/=300 nm) of methyl 2-phenyl-3,1-benzoxazepine-5-carboxylate in an alcohol afforded the Z-isomer of methyl 3-alkoxy-2-(2-benzamidophenyl)-acrylate as the major product.In contrast, thermal reaction of the oxazepine with a primary alcohol in
- Kaneko, Chikara,Fujii, Harue,Kawai, Shinji,Hashiba, Kazuhiko,Karasawa, Yoshio,et al.
-
-