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The oxidation of pyridines catalyzed by surfactant-encapsulated polyoxometalate [(C18H37)2(CH3) 2N]8[HBW11O39] with the temperature-responsive property of solubility

Temperature-responsive characterization of solubility based on a surfactant-encapsulated polyoxometalate ([(C18H37) 2(CH3)2N]8[HBW11O 39]) in tert-butyl alcohol was described and used in catalytic oxidation of pyridines. The catalyst could be recovered and reused several times by controlling the temperature.

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Iron-catalyzed deoxygenation and 2-sulfonylation of quinoline N-oxides by sodium sulfinates towards 2-sulfonyl quinolines

An iron(III)-catalyzed protocol towards 2-sulfonyl quinolines from quinoline N-oxides and sodium sulfinates was herein illustrated. The general and direct option featured for high efficiency (up to 91% yields) and good functional compatibilities (27 examples) in the Fe(III)-catalysis. Moreover, free radical mechanism was proposed for the one-pot deoxygenation and sulfonylation reaction based on the results of the control reactions.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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Substituent effects of iridium complexes for highly efficient red OLEDs

This study reports substituent effects of iridium complexes with 1-phenylisoquinoline ligands. The emission spectra and phosphorescence quantum yields of the complexes differ from that of tris(1-phenylisoquinolinato-C 2, N) iridium(in) (Irpiq) depending on the substituents. The maximum emission peak, quantum yield and lifetime of those complexes ranged from 598-635 nm, 0.17-0.32 and 1.07-2.34 mus, respectively. This indicates the nature of the substituents has a significant influence on the kinetics of the excited-state decay. The substituents attached to phenyl ring have an influence on a stability of the HOMO. Furthermore, those substituents have effect on the contribution to a mixing between 3pi-pi and 3MLCT for the lowest excited states. Some of the complexes display the larger quantum yield than Irpiq, which has the quantum yield of 0.22. The organic light emitting diode (OLED) device based on tris [1-(4-fluoro-5-methylphenyl) isoquinolinato-C2,N]iridium(III) (Ir4F5Mpiq) yielded high external quantum efficiency of 15.5% and a power efficiency of 12.41m W-1 at a luminance of 218 cd m-2. An emission color of the device was close to an NTSC specification with CIE chromaticity characteristics of (0.66, 0.34). The Royal Society of Chemistry 2005.

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Isoquinoline – Wikipedia,
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New synthesis of 2-heteroarylperfluoropropionic acids derivatives by reaction of azine N-oxides with hexafluoropropene

Hexafluoropropene reacts with aromatic azine N-oxides under mild conditions to produce fluorides of 2-heteroarylperfluoropropionic acids. The reaction proceeds as 1,3-dipolar cycloaddition followed by spontaneous scission of the N-O bond in the isoxazolidine ring and elimination of HF. When the reaction is carried out in the presence of alcohols or N-alkyl anilines, the in situ formed acyl fluorides give the corresponding esters and amides. They can be also treated separately with nucleophiles to produce the respective acylation products, whereas their hydrolysis leads to unstable carboxylic acids that undergo spontaneous decarboxylation to 1 -aryl-1,2,2,2-tetrafluoroethanes. This new reaction provides a simple and general method of synthesizing 2-heteroarylperfluoropropionic acid derivatives that were previously unknown and unavailable.

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Dendrobium huoshanense polysaccharide prevents ethanol-induced liver injury in mice by metabolomic analysis

The prevalence of alcohol consumption has increased in modern dietary life and alcoholic liver injury can follow. Dendrobium huoshanense polysaccharide (DHP) is a homogeneous polysaccharide isolated from Dendrobium huoshanense, which possesses hepatoprotection function. In this study, we investigated the metabolic profiles of serum and liver tissues extracts from control, ethanol-treated and DHPethanol-treated mice using a UHPLC/LTQ Orbitrap XL MS-based metabolomics approach. Our results indicated that DHP alleviated early steatosis and inflammation in liver histology and the metabolomic analysis of serum and hepatic tissue revealed that first, ethanol treatment mainly altered phosphatidylcholines (PCs) including PC (13:0) and phosphocholine, arachidonic acid metabolites including 20-ethyl PGF2alpha and amino acids including l-Proline; Second, DHP supplementation ameliorated the altered metabolic levels particularly involved in phosphocholine and l-Proline. These data suggested that DHP might restore the perturbed metabolism pathways by ethanol exposure to prevent the progression of alcoholic liver injury.

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Copper-Catalyzed Regioselective Cascade Alkylation and Cyclocondensation of Quinoline N-Oxides with Diazo Esters: Direct Access to Conjugated pi-Systems

An inexpensive copper-catalyzed cascade regioselective alkylation, followed by cyclocondensation of quinoline N-oxides with alpha-diazo esters has been achieved successfully to provide heteroarene-containing conjugated pi-systems. The developed method is simple, straightforward, and economical with a broad range of substrate scope. The dual role of copper catalyst in the C?H bond functionalization and in Lewis acid-promoted cyclization was explored.

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Natural Abundance 17O NMR Spectroscopy of Heterocyclic N-Oxides and Di N-Oxides. Structural Effects

The 17O chemical shift data for a series of azine N-oxides, diazine N-oxides and di-N-oxides at natural abundance are reported.Isomeric methyl substituted quinoline N-oxides exhibited chemical shifts which are interpreted in terms of electronic and compressional effects.The 17O chemical shift for 8-methylquinoline N-oxide (370 ppm) is deshielded by 25 ppm more than predicted, based upon electronic considerations.The 17O chemical shift for the N-oxide of 8-hydroxyquinoline (289 ppm) is substantially shielded as result of intramolecular hydrogen bonding.The relative 17O chemical shifts for diazine N-oxides of pyrazine, pyridazine and pyrimidine follow predictions based on back donation considerations.Because of solubility limitations, spectra of only two N,N’-dioxides were obtained.The chemical shift of benzopyrazine di N-oxide in acetonitrile was shielded by 18 ppm compared to that of its mono N-oxide.

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Tertiary amine oxidation using HOF-CH3CN: A novel synthesis of N-oxides

HOF¡¤CH3CN, probably the best oxygen transfer agent organic chemistry has to offer, is easily made by bubbling diluted fluorine (10-15%) through aqueous acetonitrile solution. Used as formed without any isolation or purification, it reacts with various tertiary amines such as pyridine derivatives, polyaromatic nitrogen containing compounds and aliphatic and alicyclic ones to form the corresponding N-oxides. When two nitrogen atoms are present it is possible to make both the N-monoxides and the N,N-dioxides. The reaction times are short (a few minutes), conditions are very mild (0-25 C) and the yields range from good to excellent (70-95%).

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An efficient and chemoselective deoxygenation of hetero cyclic N-oxides using LiCl/NaBH4

A practical and novel reagent system LiCl/NaBH4 is used for the deoxygenation of N-Oxides to amines is described.

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Visible light-induced direct alpha C?H functionalization of alcohols

Considering the synthetic value of introducing active alcoholic hydroxyl group, developing C?H functionalization of alcohols is of significance. Herein, we present a photochemical method that under visible light irradiation, selectfluor can effectively promote the oxidative cross-coupling between alcohols and heteroarenes without the external photocatalysis, achieving the selective alpha sp3 C?H arylation of alcohol, even in the presence of ether. The N-F activation of selectfluor under blue LEDs irradiation is evidenced by electron paramagnetic resonance (EPR) study, which is the key process for the oxidative activation of alpha sp3 C?H alcohols. The observed reactivity may have significant implications for chemical transformations.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem