- An alkoxyamine compound, alkoxy alcohol oxidation catalyst and method of using the alcohol oxidation
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PROBLEM TO BE SOLVED: To provide a novel alkoxyamine compound which can be easily manufactured and applied suitably as an alcohol oxidation catalyst capable of exerting sufficiently high catalytic activity in oxidation of primary and secondary alcohols.SOLUTION: There is provided an alkoxyamine compound with a homoadamantane skeleton represented by the general formula (1) in the figure. [In the formula (1), Rand Rare each independently any one selected from the group consisting of a hydrogen atom and alkyl groups that may be substituted.
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Paragraph 0096; 0099-0100
(2017/02/02)
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- Highly efficient aerobic oxidation of alcohols by using less-hindered nitroxyl-radical/copper catalysis: Optimum catalyst combinations and their substrate scope
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The oxidation of alcohols into their corresponding carbonyl compounds is one of the most fundamental transformations in organic chemistry. In our recent report, 2-azaadamantane N-oxyl (AZADO)/copper catalysis promoted the highly chemoselective aerobic oxidation of unprotected amino alcohols into amino carbonyl compounds. Herein, we investigated the extension of the promising AZADO/copper-catalyzed aerobic oxidation of alcohols to other types of alcohol. During close optimization of the reaction conditions by using various alcohols, we found that the optimum combination of nitroxyl radical, copper salt, and solution concentration was dependent on the type of substrate. Various alcohols, including highly hindered and heteroatom-rich ones, were efficiently oxidized into their corresponding carbonyl compounds under mild conditions with lower amounts of the catalysts.
- Sasano, Yusuke,Kogure, Naoki,Nishiyama, Tomohiro,Nagasawa, Shota,Iwabuchi, Yoshiharu
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p. 1004 - 1009
(2015/03/31)
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- IRAK INHIBITORS AND USES THEREOF
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The present invention provides quinazoline and quinoline compounds, compositions thereof, and methods of using the same. Also disclosed is the activity of such compounds as inhibitors of IRAK enzymes.
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- Mechanistic insight into aerobic alcohol oxidation using NOx-nitroxide catalysis based on catalyst structure-activity relationships
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The mechanism of an NOx-assisted, nitroxide(nitroxyl radical)-catalyzed aerobic oxidation of alcohols was investigated using a set of sterically and electronically modified nitroxides (i.e., TEMPO, AZADO (1), 5-F-AZADO (2), 5,7-DiF-AZADO (3), 5-MeO-AZADO (4), 5,7-DiMeO-AZADO (5), oxa-AZADO (6), TsN-AZADO (7), and DiAZADO (8)). The motivation for the present study stemmed from our previous observation that the introduction of an F atom at a remote position from the nitroxyl radical moiety on the azaadamantane nucleus effectively enhanced the catalytic activity under typical NOx-mediated aerobic-oxidation conditions. The kinetic profiles of the azaadamantane-N-oxyl-[AZADO (1)-, 5-F-AZADO (2)-, and 5,7-DiF-AZADO (3)]-catalyzed aerobic oxidations were closely investigated, revealing that AZADO (1) showed a high initial reaction rate compared to 5-F-AZADO (2) and 5,7-DiF-AZADO (3); however, AZADO-catalyzed oxidation exhibited a marked slowdown, resulting in ~90% conversion, whereas 5-F-AZADO-catalyzed oxidation smoothly reached completion without a marked slowdown. The reasons for the marked slowdown and the role of the fluoro group are discussed. Oxa-AZADO (6), TsN-AZADO (7), and DiAZADO (8) were designed and synthesized to confirm their comparable catalytic efficiency to that of 5-F-AZADO (2), providing supporting evidence for the electronic effect on the catalytic efficiency of the heteroatoms under NOx-assisted aerobic-oxidation conditions.
- Shibuya, Masatoshi,Nagasawa, Shota,Osada, Yuji,Iwabuchi, Yoshiharu
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p. 10256 - 10268
(2015/02/19)
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- FLT3 INHIBITORS AND USES THEREOF
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The present invention provides methods of using compounds of formula I: or compositions thereof for the inhibition of FLT3, and the treatment of FLT3-mediated disorders.
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- 3-methyl-4-oxa-5-azahomoadamantane: Alkoxyamine-type organocatalyst for alcohol oxidation
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Strong, silent type: A novel alkoxyamine-type organocatalyst has been discovered for alcohol oxidation (see scheme). The alkoxyamine exhibits a high catalytic activity for the oxidation of alcohols to afford the corresponding carbonyl compounds in high yield by oxidative transformation into an oxoammonium ion, which is proposed to serve as an active species. Copyright
- Sasano, Yusuke,Murakami, Keiichi,Nishiyama, Tomohiro,Kwon, Eunsang,Iwabuchi, Yoshiharu
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supporting information
p. 12624 - 12627
(2013/12/04)
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- METHOD FOR OXIDIZING ALCOHOLS
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A method for oxidizing an alcohol, wherein oxidation is performed in the presence of a compound represented by the following formula (I) and a bulk oxidant, which enables efficient oxidation of secondary alcohols as well as primary alcohols, and can attain high reaction efficiency even when air is used as a bulk oxidant.
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Paragraph 0101; 0102
(2013/06/05)
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- Highly efficient Cu(I)-catalyzed oxidation of alcohols to ketones and aldehydes with diaziridinone
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A novel and efficient Cu(I)-catalyzed oxidation of alcohols has been achieved with di-tert-butyldiaziridinone as the oxidant under mild conditions. A wide variety of primary and secondary alcohols with various functional groups can be oxidized to aldehydes and ketones in high yields. The reaction proceeds under neutral conditions making it compatible with acid- or base-sensitive substrates, and it is amenable to gram scale.
- Zhu, Yingguang,Zhao, Baoguo,Shi, Yian
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supporting information
p. 992 - 995
(2013/04/10)
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- Oxidation of alcohols to carbonyl compounds with diisopropyl azodicarboxylate catalyzed by nitroxyl radicals
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A nitroxyl-radical-catalyzed oxidation of alcohols using diisopropyl azodicarboxylate (DIAD) as the terminal oxidantis reported. A variety of primary and secondary alcohols including aliphatic, benzylic, and allylic alcohols are efficiently oxidized to their corresponding aldehydes and ketones without overoxidation to carboxylic acid. 1,2-Diols are oxidized to hydroxyl ketones or diketones depending on the amount of DIAD used.
- Hayashi, Masaki,Shibuya, Masatoshi,Iwabuchi, Yoshiharu
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experimental part
p. 3005 - 3009
(2012/05/04)
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- 9-azanoradamantane N-Oxyl (Nor-AZADO): A highly active organocatalyst for alcohol oxidation
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A highly active organocatalyst for alcohol oxidation has been developed. 9-Azanoradamantane N-oxyl (Nor-AZADO 4), constituting an unhindered, stable nitroxyl radical, exhibits superior catalytic activity to 2,2,6,6- tetramethylpiperidine-1-oxyl (TEMPO) and AZADOs in the oxidation of alcohols to their corresponding carbonyl compounds.
- Hayashi, Masaki,Sasano, Yusuke,Nagasawa, Shota,Shibuya, Masatoshi,Iwabuchi, Yoshiharu
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experimental part
p. 1570 - 1573
(2012/01/05)
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- Synthesis and solution properties of pH responsive methoxy poly(ethylene glycol)-b-poly(γ-amino-ε-caprolactone)
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A series of water-soluble and cationic methoxy poly(ethylene glycol)-b-poly(γ-amino-ε-caprolactone) (mPEG-b-PACL) has been synthesized via ring opening polymerization of γ-(carbamic acid benzyl ester)-ε-caprolactone (γCABεCL) using mPEG as a macroinitiato
- Liu, Jianjing,Zhang, Yan,Yan, Jinliang,Lang, Meidong
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p. 6677 - 6682
(2011/10/13)
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- Highly efficient, organocatalytic aerobic alcohol oxidation
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5-Fluoro-2-azaadamantane N-oxyl (5-F-AZADO) realizes a simple, organocatalytic aerobic alcohol oxidation system that has a wide scope under mild conditions at ambient pressure and temperature and is weakly acidic and halogen- and transition-metal-free. The oxoammonium nitrate (5-F-AZADO +NO3-) works as a bifunctional catalyst of 5-F-AZADO and NOx that enables the catalytic aerobic oxidation of alcohols by itself (a metal-salt-free system).
- Shibuya, Masatoshi,Osada, Yuji,Sasano, Yusuke,Tomizawa, Masaki,Iwabuchi, Yoshiharu
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supporting information; experimental part
p. 6497 - 6500
(2011/06/23)
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- Novel poly(ε-caprolactone)s bearing amino groups: Synthesis, characterization and biotinylation
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A novel functional ε-caprolactone monomer containing protected amino groups, γ-(carbamic acid benzyl ester)-ε-caprolactone (γCABεCL), was successfully synthesized. A series of copolymers [poly(CL-co-CABCL)] were prepared by ring-opening polymerization of
- Yan, Jinliang,Zhang, Yi,Xiao, Yan,Zhang, Yan,Lang, Meidong
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p. 400 - 407
(2011/12/01)
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- Serotonin derivatives as a new class of non-ATP-competitive receptor tyrosine kinase inhibitors
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The discovery of new templates and their subsequent elaboration to clinically useful receptor tyrosine kinase (RTK) inhibitors continues to be an important issue. RTKs are a class of enzymes responsible for the activation of different cellular signal transduction cascades. The majority of the known small molecules RTK inhibitors are ATP-competitive and they are multiple targeted inhibitors. We describe here serotonin derivatives as a new class of multiple targeted RTK inhibitors. In contrast to most other RTK inhibitors they act via a non-ATP-competitive (allosteric) mechanism. Furthermore, they are able to inhibit the proliferation of HUVE cells, fibroblasts and two cancer cell lines.
- Büttner, Anita,Cottin, Thomas,Xu, Jing,Tzagkaroulaki, Lito,Giannis, Athanassios
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experimental part
p. 3387 - 3402
(2010/10/03)
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- TETRAHYDROCARBAZOLE DERIVATIVES USEFUL AS ANDROGEN RECEPTOR MODULATORS
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The present invention provides a compound of the formula: Formula I or a pharmaceutically acceptable salt thereof; pharmaceutical compositions comprising an effective amount of a compound of Formula I in combination with a suitable carrier, diluent, or ex
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Page/Page column 147-148
(2010/11/25)
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- 2-Amino-4-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors
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Novel compounds are provided which are glycogen phosphorylase inhibitors which are useful in treating, preventing or slowing the progression of diseases requiring glycogen phosphorylase inhibitor therapy such as diabetes and related conditions (such as hy
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Page/Page column 29
(2010/11/08)
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- (Spirocyclylamido)aminothiophene compounds
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Compounds represented by Formula (I): or a pharmaceutically acceptable salt or N-oxide thereof, wherein A, R1, X and Y are defined herein, are useful in the treatment of tumors and cancers such as mastocytosis/mast cell leukemia, gastrointestin
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Page/Page column 10
(2010/10/20)
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- Phenol compound having antioxidative activity and the process for preparing the same
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Disclosed are a phenol compound represented by the formula (1): STR1 wherein R0 represents H, alkyl or alkyloxy; R1 represents alkyl; R2 represents alkyl or alkyloxy; OR3 represents OH; R4 represents H, lower alkyl or acyl, each of the above substituents may be substituted; W represents O, S or NR7 ; where R7 represents H, alkyl, aryl, OH or alkyloxy, a group of the formula (2): STR2 represents an amino which may be mono- or di-substituted or heterocyclic group containing N atom, or a pharmaceutically acceptable salt thereof, and a process for preparing the same.
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- Terminally modified tri-, tetra- and pentapeptide anaphylatoxin receptor ligands
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Oligopeptide compounds or oligopeptide analogue compounds of the formula A-B-D-E-G-J-L are ligands for the anaphylatoxin receptor and are useful in the treatment of inflammatory disease states. Also disclosed are anaphylatoxin receptor ligand compositions
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- Syntheses of the Saturated Analogues of 4-Nitrophenol and 4-Nitroaniline
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Two syntheses for 4-nitrocyclohexanol and 4-nitrocyclohexanamine are presented.Both conveniently start from commercially available 4-aminocyclohexanol.
- Janda, Kim D.,Ashley, Jon A.
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p. 1073 - 1082
(2007/10/02)
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