- Preparation of substituted quinolinyl and isoquinolinyl sulfonyl chlorides for the synthesis of novel sulfonamides
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Novel sulfonyl chlorides of quinolines and isoquinolines have successfully been prepared. This enabled the preparation of the corresponding sulfonamides via reaction with an amine using the "resin-capture and release" methodology.
- Lai, Justine Y. Q.,Ferguson, Yvonne,Jones, Mark
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- Novel quinazoline-quinoline alkaloids with cytotoxic and DNA topoisomerase II inhibitory activities
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Two new synthetic analogues of luotonins A and F, 7-acetylaminoluotonin A (6) and 3-[3H(quinazolino-4-one)]quinoline (7) were synthesized. The new analogues, along with four natural quinazoline-quinoline alkaloids, luotonins A (1), B (2), E (3), F (4) and a synthetic deoxoluotonin F (5), showed cytotoxic activity (IC50 1.8-40.0 μg/mL) and DNA topoisomerase II inhibition at a concentration of 25 μM.
- Ma, Zhongze,Hano, Yoshio,Nomura, Taro,Chen, Yingjie
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- Direct Oxidative Amination of the Methyl C-H Bond in N-Heterocycles over Metal-Free Mesoporous Carbon
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Direct oxidative amination of the sp3C-H bond is an attractive synthesis route to obtain amides. Conventional catalytic systems for this transformation are based on transition metals and complicated synthesis processes. Herein, direct and efficient oxidative amination of the methyl C-H bond in a wide range of N-heterocycles to access the corresponding amides over metal-free porous carbon is successfully developed. To understand the fundamental structure-activity relationships of carbon catalysts, the surface functional groups and the graphitization degree of porous carbon have been purposefully tailored through doping with nitrogen or phosphorus. The results of characterization, kinetic studies, liquid-phase adsorption experiments, and theoretical calculations indicate that the high activity of the carbon catalyst is attributed to the synergistic effect of surface acidic functional groups (hydroxyl/carboxylic acid/phosphate) and more graphene edge structures exposed on the surface of carbon materials with a high graphitization degree, in which the role of acidic functional groups is to adsorb the substrate molecule and the role of the graphene edge structure is to activate O2
- Long, Xiangdong,Wang, Jia,Gao, Guang,Nie, Chao,Sun, Peng,Xi, Yongjie,Li, Fuwei
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p. 10902 - 10912
(2021/09/08)
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- Sodium sulphide promoted synthesis of fused quinoline at room temperature
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A novel, simple and eco-friendly strategy for the synthesis of thiopyrano[4,3-b]quinolin-1-ones and pyrrolo[3,4-b]quinolin-1-ones from 2-alkynylquinoline-3-carbonitriles and sodium sulphide (Na2S·9H2O) under catalyst-free conditions at room temperature has been described. In this reaction, a readily available inorganic salt (Na2S·9H2O) serves as the sulphur source and leads to the generation of diverse functionalized thiopyrano[4,3-b]quinolin-1-ones and pyrrolo[3,4-b]quinolin-1-ones in moderate to excellent yields through sulfuration, annulation, and aerial oxidation.
- Singh, Rashmi,Sharma, Vishal Prasad,Yadav, Priyanka,Sonker, Priyanka,Singh, Radhey Mohan,Tewari, Ashish Kumar
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supporting information
p. 8108 - 8112
(2021/10/04)
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- Water-soluble superbulky (η6- p -cymene) ruthenium(ii) amine: An active catalyst in the oxidative homocoupling of arylboronic acids and the hydration of organonitriles
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A phosphine free water-soluble superbulky amine-ruthenium-arene complex (2) encompassing 2,6-bis(diphenylmethyl)-4-methylaniline was synthesised in good yield. 2 was characterized by FT-IR, 1H NMR, and 13C NMR spectroscopies, TGA and elemental analyses. The structure of 2 was confirmed by a single-crystal X-ray diffraction study. The ruthenium centre in 2 adopts the pseudo-octahedral geometry due to the η6-p-cymene ring and bulky aniline ligand along with two chloro groups. Besides, complex 2 was efficaciously employed as a catalyst in the hydration of organonitriles to amides. This reaction proceeds efficiently for a wide range of substrates in an environmentally benign medium and is an economically reasonable synthetic route to amides in good yields. In addition, 2 acts as an excellent catalyst in the oxidative homocoupling of arylboronic acids in water. A range of arylboronic acids undergo a homocoupling reaction in the presence of catalyst 2 to yield symmetrical biaryls in reasonable to good yields.
- Nirmala, Muthukumaran,Adinarayana, Mannem,Ramesh, Karupnaswamy,Maruthupandi, Mannarsamy,Vaddamanu, Moulali,Raju, Gembali,Prabusankar, Ganesan
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supporting information
p. 15221 - 15230
(2018/09/29)
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- Ruthenium(II) complexes incorporating salicylaldiminato-functionalized N-heterocyclic carbene ligands as efficient and versatile catalysts for hydration of organonitriles
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We describe a new synthetic procedure for synthesis of ruthenium(II) complexes containing salicylaldiminato functionalized mixed N-heterocyclic carbene (NHC) ligand and phosphine co-ligand. The complexes (3a-3d) have been obtained in good to excellent yields by transmetalation from the corresponding Ag-NHC complexes (2a-2d) as carbene transfer reagents. All the [Ru-NHC] complexes have been characterized by elemental analyses, spectroscopic methods as well as ESI mass spectrometry. The ligands 1a-1d show their versatility by switching to be O,N,C-chelating in these ruthenium(II) complexes. The resulting complexes have been evaluated as potential catalysts for the selective hydration of nitriles to primary amides, and related amide bond forming reactions, in environmentally friendly medium. The reaction tolerated ether, hydroxyl, nitro, bromo, formyl, pyridyl, benzyl and alkyl functional groups. The catalyst was stable for weeks and could be recovered and reused more than six times without significant loss of activity.
- Nirmala, Muthukumaran,Saranya, Gandhi,Viswanathamurthi, Periasamy
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p. 134 - 144
(2016/01/09)
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- Pd(0)-mediated [11C]carbonylation of aryl and heteroaryl boronic acid pinacol esters with [11C]carbon monoxide under ambient conditions and a facile process for the conversion of [carbonyl-11C]esters to [carbonyl-11C]amides
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A new method has been developed for the Pd(0)-mediated [11C]carbonylation of aryl/heteroaryl boronic acid pinacol esters with [11C]carbon monoxide in the presence of p-benzoquinone and triphenylphosphine in a mixture of N,N-dimethylformamide (DMF) and methanol (MeOH) or just MeOH under ambient pressure at 65 °C. This method was used to convert a variety of different aryl/heteroaryl boronates to the corresponding [carbonyl-11C]esters with decay-corrected radiochemical yields in the range of 6-80%. Furthermore, some of these [carbonyl-11C]esters were treated with sodium hydroxide or aqueous ammonium to give the corresponding [carbonyl-11C]carboxylic acids and amides, respectively. This new method was also used to achieve the direct syntheses of [11C]aspirin using water or tetramethylammonium hydroxide as the nucleophile instead of MeOH in DMF.
- Ishii, Hideki,Minegishi, Katsuyuki,Nagatsu, Koutaro,Zhang, Ming-Rong
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supporting information
p. 1588 - 1596
(2015/03/04)
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- Palladium-catalyzed synthesis of primary benzamides from aryl bromides via a cyanation and hydration sequence
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An interesting and effective procedure for the synthesis of benzamides from aryl bromides has been developed. In the presence of a palladium catalyst, various primary benzamides have been produced in moderate to excellent yields in a one-pot one-step manner.
- Sharif, Muhammad,Wu, Xiao-Feng
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p. 21001 - 21004
(2015/03/30)
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- Substrate-Specific Heterogeneous Catalysis of CeO2 by Entropic Effects via Multiple Interactions
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Achieving complete substrate specificity through multiple interactions like an enzyme is one of the ultimate goals in catalytic studies. Herein, we demonstrate that multiple interactions between the CeO2 surface and substrates are the origin of substrate-specific hydration of nitriles in water by CeO2, which is exclusively applicable to the nitriles with a heteroatom (N or O) adjacent to the α-carbon of the CN group but is not applicable to the other nitriles. Kinetic studies reveal that CeO2 reduces the entropic barrier (TΔS?) for the reaction of the former reactive substrate, leading to 107-fold rate enhancement compared with the latter substrate. Density functional theory (DFT) calculations confirmed multiple interaction of the reactive substrate with CeO2, as well as preferable approximation and alignment of the nitrile group of the substrate to the active OH group on CeO2 surface. This can lead to the reduction of the entropic barrier. This is the first example of an entropy-driven substrate-specific catalysis of a nonporous metal oxide surface, which will provide a new design strategy for enzyme-inspired synthetic catalysts.
- Tamura, Masazumi,Sawabe, Kyoichi,Tomishige, Keiichi,Satsuma, Atsushi,Shimizu, Ken-Ichi
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- Mild and selective heterogeneous catalytic hydration of nitriles to amides by flowing through manganese dioxide
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A sustainable flow chemistry process for the hydration of nitriles, whereby an aqueous solution of the nitrile is passed through a column containing commercially available amorphous manganese dioxide, has been developed. The product is obtained simply by concentration of the output stream without any other workup steps. The protocol described is rapid, robust, reliable, and scalable, and it has been applied to a broad range of substrates, showing a high level of chemical tolerance.
- Battilocchio, Claudio,Hawkins, Joel M.,Ley, Steven V.
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supporting information
p. 1060 - 1063
(2016/10/17)
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- Iron-catalyzed cascade reaction of ynone with o-aminoaryl compounds: A Michael addition-cyclization approach to 3-carbonyl quinolines
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An efficient iron-catalyzed cascade Michael addition-cyclization of o-aminoaryl compounds including o-aminoaryl aldehydes, o-aminoaryl ketones, and o-aminobenzyl alcohols with ynones for the synthesis of 3-carbonyl quinolines is reported. The reactions proceed to afford 3-carbonyl quinoline derivatives with or without substituent at the C-4 position in good to high yields using Iron(III) chloride hexahydrate as the catalyst in the air.
- Li, Hongfeng,Xu, Xiaolei,Yang, Jingyu,Xie, Xin,Huang, He,Li, Yanzhong
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supporting information; experimental part
p. 530 - 533
(2011/02/28)
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- HYDROXYAPATITE WITH SILVER SUPPORTED ON THE SURFACE THEREOF
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An object of the present invention is to provide a hydroxyapatite with silver supported on the surface thereof, a new compound useful as a catalyst for the reaction of producing an amide compound by hydration of the corresponding nitrile compound. The hydroxyapatite with silver supported on the surface thereof according to the present invention is obtained by supporting zero-valent Ag on the surface of a hydroxyapatite. Also provided are a hydroxyapatite with silver supported on the surface thereof used as a catalyst, and a method for producing an amide compound, comprising producing the amide compound by hydration of the corresponding nitrile compound in the presence of a hydroxyapatite with silver supported on the surface thereof having zero-valent Ag supported on the surface of the hydroxyapatite.
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Page/Page column 8
(2011/01/11)
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- Supported silver nanoparticle catalyst for selective hydration of nitriles to amides in water
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Hydroxyapatite-supported silver nanoparticles (AgHAP) acted as a highly efficient reusable heterogeneous catalyst for hydration of diverse nitriles, including heteroaromatic ones, into amides in water.
- Mitsudome, Takato,Mikami, Yusuke,Mori, Haruhiko,Arita, Shusuke,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
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supporting information; scheme or table
p. 3258 - 3260
(2009/12/01)
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- Small-molecule inhibitors of histone acetyltransferase activity: Identification and biological properties
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Starting from a yeast phenotypic screening performed on 21 compounds, we described the identification of two small molecules (9 and 18) able to significantly reduce the S. cerevisiae cell growth, thus miming the effect of GCN5 deletion mutant. Tested on a GCN5-dependent gene transcription assay, compounds 9 and 18 gave a high reduction of the reporter activity. In S. cerevisiae histone H3 terminal tails assay, the H3 acetylation levels were highly reduced by treatment with 0.6-1 mM 9, while 18 was effective only at 1.5 mM. In human leukemia U937 cell line, at 1 mM 9 and 18 showed effects on cell cycle (arrest in G1 phase, 9), apoptosis (9), and granulocytic differentiation (18). When tested on U937 cell nuclear extracts to evaluate their histone acetyltransferase (HAT) inhibitory action, both compounds were able to reduce the enzyme activity when used at 500 μM. Another quinoline, compound 22, was synthesized with the aim to improve the activity observed with 9 and 18. Tested in the HAT assay, 22 was able to reduce the HAT catalytic action at 50 and 25 μM, thereby being comparable to anacardic acid, curcumin, and MB-3 used as references. Finally, in U937 cells, compounds 9 and 18 used at 2.5 mM were able to reduce the extent of the acetylation levels of histone H3 (9) and α-tubulin (9 and 18). In the same assay, 22 at lower concentration (100 μM) showed the same hypoacetylating effects with both histone and non-histone substrates.
- Mai, Antonello,Rotili, Dante,Tarantino, Domenico,Ornaghi, Prisca,Tosi, Federica,Vicidomini, Caterina,Sbardella, Gianluca,Nebbioso, Angela,Miceli, Marco,Altucci, Lucia,Filetici, Patrizia
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p. 6897 - 6907
(2007/10/03)
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- FURTHER FUNCTIONAL GROUP OXIDATIONS USING SODIUM PERBORATE
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Sodium perborate in acetic acid is an effective reagent for the oxidation of aromatic aldehydes to carboxylic acids, iodoarenes to (diacetoxyiodo)arenes, azines to N-oxides, and various types of sulfur heterocycles to S,S-dioxides.Nitriles are unaffected by the reagent in acetic acid, but undergo smooth hydration to amides when aqueous methanol is employed as solvent.
- McKillop, Alexander,Kemp, Duncan
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p. 3299 - 3306
(2007/10/02)
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- Syntheses and Reactions of Diazepinoquinolines
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Three routes for the preparation of diazepinoquinolines (1) have been studied.The best yields resulted by starting from the amides of N-(3-quinolylcarbonyl)-N-alkyl-amino acids (5).Quaternization to 9, intramolecular cyclization under the influence of base to 10, oxidation to 11 and debenzylation by catalytic hydrogenation gave 1. - Keywords: Quinolinium Salts, Cyclization Reaction
- Guendel, Wolf-H.,Bohnert, Sabine
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p. 769 - 777
(2007/10/02)
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- Kinetic and thermodynamic control of pseudobase formation from C-3 substituted 1-methylquinolinium cations
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The kinetic and thermodynamic control of pseudobase formation from 3-W-1-methylquinolinium cations has been studied for a variety of substituents (W).Spectral data indicate that, in both aqueous and methanolic solution, the C-2 pseudobases predominate at equilibrium for W=H and Br, while the C-4 pseudobases are thermodynamically preferred species for W=CONH2, CO2CH3, CN, and NO2.Stopped-flow studies indicate that in all cases the C-2 pseudobases are the kinetically-controlled products upon basification of the aqueous solutions of these cations.Equilibrium constants (pKR+) have been measured for pseudobase formation at both C-2 and C-4 for each W in all cases where they are experimentally accessible.Substituent effects upon pK2R+ correlate with ?m for W, while pK4R+ depends upon ?-p.These substituent effects allow the prediction of pK2R+ = 15.4 and pK4R+ = 17.4 for the 1-methylquinolinium cation.Rates of C-2 to C-4 pseudobase equilibration have been measured in all cases where the latter species is thermodinamically more stable.These kinetic data allow the evaluation of rate constants for C-4 pseudobase equilibration with each cation.In all cases except W=CN, C-2 pseudobase formation is complete within the mixing time of the stopped-flow instrument.
- Bunting, John W.,Fitzgerald, Norman P.
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p. 1301 - 1307
(2007/10/02)
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