- A practical, efficient, and rapid method for the oxidation of electron deficient pyridines using trifluoroacetic anhydride and hydrogen peroxide- urea complex
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A general method for the oxidation of electron-poor pyridines to their N-oxides using UHP and TFAA in either CH2Cl2 or CH3CN was developed. The methodology proved to tolerate a number of functional groups and substitution
- Caron, Stéphane,Do, Nga M.,Sieser, Janice E.
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Read Online
- Pd-Catalyzed Direct C-H Alkenylation and Allylation of Azine N -Oxides
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A Pd-catalyzed direct C2-alkenylation of azine N-oxides with allyl acetate is disclosed. The products are formed through an allylation/isomerization cascade process. The use of a tri-tert-butylphosphonium salt as the ligand precursor and KF is mandatory for optimal yields. When cinnamyl acetate is used, the same catalytic system promotes C2-cinnamylation of the azine N-oxide without subsequent isomerization. A mechanism is proposed on the basis of experimental studies and DFT calculations.
- Roudesly, Fares,Veiros, Luis F.,Oble, Julie,Poli, Giovanni
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supporting information
p. 2346 - 2350
(2018/04/30)
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- A lipase-glucose oxidase system for the efficient oxidation of: N -heteroaromatic compounds and tertiary amines
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In this work, a lipase-glucose oxidase system has been designed and proven to be an efficient system for the oxidation of N-heteroaromatic compounds and tertiary amines. This dual-enzyme system not only displays environmental friendliness, but also demonstrates its huge potential in industrial applications.
- Yang, Fengjuan,Zhang, Xiaowen,Li, Fengxi,Wang, Zhi,Wang, Lei
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supporting information
p. 3518 - 3521
(2016/07/06)
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- Base free regioselective synthesis of α-triazolylazine derivatives
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A regioselective α-heteroarylation followed by deoxygenation towards the synthesis of variety of azine triazole from simple azine N-oxides derivatives and N-tosyl-1,2,3-triazoles has been described. The reaction is metal free and base free with shorter reaction time, high yields and a broad substrate scope.
- Harisha, Mysore Bhyrappa,Nagaraj, Muthupandi,Muthusubramanian, Shanmugam,Bhuvanesh, Nattamai
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p. 58118 - 58124
(2016/07/06)
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- Grafting of a rhenium-oxo complex on Schiff base functionalized graphene oxide: An efficient catalyst for the oxidation of amines
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A rhenium-oxo complex such as methyltrioxorhenium (MTO) has been homogeneously immobilized on a Schiff base modified graphene oxide (GrO) support via covalent bonding. The loading of MTO on GrO nanosheets was monitored by FTIR, TG-DTA, and elemental analyses. The developed heterogeneous catalyst is found to be efficient for the oxidation of various amines to the corresponding N-oxides using hydrogen peroxide as an oxidant in high to excellent yields. At the end of the reaction, the catalyst is readily recovered by filtration and reused for subsequent runs. After the third run, the catalyst showed a marginal decrease in catalytic activity owing to the leaching of the MTO complex from the support. This journal is the Partner Organisations 2014.
- Khatri, Praveen K.,Choudhary, Shivani,Singh, Raghuvir,Jain, Suman L.,Khatri, Om P.
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p. 8054 - 8061
(2014/05/20)
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- CHROMAN - SPIROCYCLIC PIPERIDINE AMIDES AS MODULATORS OF ION CHANNELS
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The invention relates to chroman spirocyclic piperidine amide derivatives useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.
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Page/Page column 73-74
(2012/09/10)
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- 3-Hydroxypyrrolo[2,3-b]pyridine and related compounds - Indoxyl analogues with fused electron deficient rings
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Flash vacuum pyrolysis (FVP) of 4-acetyltetrazolo[1,5-a]pyridine 5 at 400 °C provides 3-methyl isoxazolo[3,4-b]pyridine 6 whose structure was confirmed by X-ray crystallography. At higher pyrolysis temperatures, the unstable heteroindoxyl 8 was obtained, which exists as the keto form (1,2-dihydropyrrolo[2,3-b]pyridin-3-one) 8K in CDCl3 solution and the enol tautomer (3-hydroxypyrrolo[2,3-b]pyridine) 8E in DMSO. The heteroindoxyl 8 oxidatively dimerises to the heteroindigotin 9, undergoes condensation reactions at the 2-position and reacts with methoxymethylene Meldrum's acid at the 1-position. FVP of the corresponding acetyltetrazolo[1,5-a]quinoline 19 was much more complex, with 2-(cyanophenyl)acetonitrile 30 (rather than a heteroindoxyl) the major product at 750 °C. FVP of 3-acetyl-4-azidoquinoline 24 at 400 °C gave 3-methylisoxazolo[4,3-c]quinoline 33, but rearrangement to the heteroindoxyl was not observed at higher temperatures.
- Gaywood, Alexander P.,McNab, Hamish
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supporting information; experimental part
p. 5166 - 5173
(2010/12/25)
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- INHIBITORS OF HISTONE DEACETYLASE
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The invention relates to a series of compounds useful for inhibiting histone deacetylase (HDAC) enzymatic activity. The invention also provides a method for inhibiting histone descetylase in a cell using said compounds as well as a method for treating cell proliferative diseases and conditions using said HDAC inhibitors. Further, the invention provides pharmaceutical compositions comprising the HDAC inhibiting compounds and a pharmaceutically acceptable carrier.
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Page/Page column 73
(2010/02/14)
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- Novel synthesis of tetrahydro-2(1H)-quinolones using Diels-Alder reactions of 1-arylsulfonyl-2(1H)-pyridones having an electron-withdrawing group
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A novel synthetic methodology of preparing tetrahydro-2(1H)-quinolones by Diels-Alder reactions between 2-methyl- and 2,3-dimethyl-1,3-butadienes and 1-arylsulfonyl-2(1H)-pyridones having an electron-withdrawing group at the 5-position is presented. Furthermore, the site-selectivity analyses based on MO calculations of the 5-substituted 2(1H)-pyridones acting as the dienophiles are described.
- Fujita, Reiko,Watanabe, Kazuhiro,Ikeura, Wakako,Ohtake, Yohsuke,Hongo, Hiroshi,Harigaya, Yosihiro,Matsuzaki, Hisao
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p. 8841 - 8850
(2007/10/03)
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- A simple and efficient method for the preparation of N- heteroaromatic N-oxides
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Urea-hydrogen peroxide/formic acid system has shown utility for mild and safe N-oxidation of N-heteroaromatic compounds.
- Balicki, Roman,Golinski, Jerzy
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p. 1529 - 1534
(2007/10/03)
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- Tertiary amine oxidation using HOF-CH3CN: A novel synthesis of N-oxides
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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%).
- Dayan, Sharon,Moshe, Kol,Rozen, Shlomo
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p. 1427 - 1430
(2007/10/03)
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- Biotransformation of phenyl- and pyridylalkane derivatives in rat liver 9,000xg supernatant (S-9)
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When phenylpropanes were incubated with phenobarbital-pretreated rat liver 9,000xg supernatant (S-9), oxidative hydroxylation occurred to give phenylpropanol (racemic), (1R, 2S)- and (1R, 2R)-phenylpropanediols, (2S)-hydroxyphenylpropanone. Incubation of pyridylethane and propane with S-9 afforded α-pyridylethanol and propanol, but those were optically inactive. During the incubation of 1-phenylpropanone, an asymmetric redox reaction simultaneously occurred to give (2S)-phenylpropanol, (1R, 2S)- or (1R, 2R)-phenylpropanediols and (2R)-hydroxyphenylpropanone. Acetylpyridines were enantioselectively reduced to afford α-pyridylethanols in high optical yields (94-98%ee). The oxidation of pyridylalkane was significantly inhibited by cytochrome P-450 inhibitor (SKF-525A), but reduction of acetylpyridines was not inhibited. Thus, cytochrome P-450 was found to be responsible for the oxidation of pyridylalkane, but not for the reduction of the ketone.
- Takeshita, Mitsuhiro,Miura, Masatomo,Unuma, Yukiko,Iwai, Sakiko,Sato, Izumi,Hongo, Takahiko,Arai, Toshie,Kosaka, Kazuhiro
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p. 831 - 836
(2007/10/03)
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- Clusters 2- as Novel Catalysts in Organic Reductions
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The cluster 2- catalyzed the redudtions of nitro compounds, quinones and N-oxide compounds to amines, hydroquinones, and deoxygenated compounds, respectively, in the presence of thiols in CH3CN solution.The reaction mechanism was also investigated by electron spin resonance spectroscopy, and it was concluded that these reactions proceed via one-electron transfer from the cluster to the substrates.Keywords - ferredoxin; cluster; electron transfer; iron-sulfur protein; reduction; superoxidized cluster
- Itoh, Takashi,Nagano, Tetsuo,Hirobe, Masaaki
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p. 2013 - 2017
(2007/10/02)
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- Alkylation of Pyridine N-Oxides by Compounds with Active Methylene Protons
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Alkylation of nicotinic acid ethyl ester and 3-acetylpyridine N-oxides by compounds with active methylene protons is described. The tautomerism in products is observed and composition of tautomeric mixture for each product is determined.
- Mieczkowski, Jozef B.
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p. 255 - 259
(2007/10/02)
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