- Efficient oxidation of cycloalkanols by sodium nitrite with molecular oxygen in trifluoroacetic acid
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Oxidation of aliphatic cycloalkanols by sodium nitrite in trifluoroacetic acid gave α,ω-dicarboxylic acids in good yields. Adipic acid was obtained in a quantitative yield from cyclohexanol using 1 equiv of sodium nitrite under oxygen atmosphere but the oxidation required more than 3 equiv of sodium nitrite under nitrogen atmosphere. The oxidation method was applicable to the conversion of 1-alkanols to the corresponding carboxylic acids.
- Matsumura, Yoshihiro,Yamamoto, Yutaka,Moriyama, Noriaki,Furukubo, Shigeru,Iwasaki, Fumiaki,Onomura, Osamu
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- Sustainable electroorganic synthesis of lignin-derived dicarboxylic acids
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The oxidative ring opening of lignin-derived alkylated cyclohexanols to bio-based alkylated dicarboxylic acids is successfully performed by an electrocatalytic conversion. To establish this transformation as a green method, we developed a simple protocol for the anodic oxidation at nickel oxide-hydroxide (NiOOH) foam anodes in caustic soda in both a batch and flow electrolysis approach.
- Rauen, Anna Lisa,Waldvogel, Siegfried R.,Weinelt, Frank
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- A new, modulated, oxidative ring cleavage of α-nitrocycloalkanones by Oxone: Synthesis of α,ω-dicarboxylic acids and α,ω-dicarboxylic acid monomethyl esters
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By the appropriate choice of the reaction conditions Oxone produces the ring cleavage of α-nitrocycloalkanones affording good yields of α,ω-dicarboxylic acids and α,ω-dicarboxylic acid monomethyl esters, respectively, regardless the ring size and/or the presence of an alkyl group as substituent.
- Ballini, Roberto,Curini, Massimo,Epifano, Francesco,Marcotullio, Maria Carla,Rosati, Ornelio
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- A New Oxidative Cleavage of 2-Nitrocycloalkanones by Hydrogen Peroxide: An Important, Efficient Method for Dicarboxylic Acid or Ketoacid Synthesis
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2-Nitrocycloalkanones are smoothly converted into dicarboxylic acids or ketoacids, depending on whether the nitro group is secondary or tertiary, by treatment with aqueous 30percent hydrogen peroxide and potassium carbonate in methyl alcohol solution for 8-10 h at room temperature.
- Ballini, Roberto,Marcantoni, Enrico,Petrini, Marino,Rosini, Goffredo
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- Oxidation of homochiral ketals by rhenium(VII) oxide. V
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2-Hydroxyethyl enol ethers react with Re2O7 to produce 2-hydroxyketals. Where homochiral starting enol ethers are employed, greater than 99:1 diastereoselectivities are obtained. The stereocontrol is rationalized by invoking a transition state that approximates the geometry of a metallaoxetane. Finally, homochiral ketals are themselves oxidized to provide 2-hydroxyketals with high diastereoselectivity.
- Tang,Kennedy
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- Discovery and Optimization of a Compound Series Active against Trypanosoma cruzi, the Causative Agent of Chagas Disease
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Chagas disease is caused by the protozoan parasite Trypanosoma cruzi. It is endemic in South and Central America and recently has been found in other parts of the world, due to migration of chronically infected patients. The current treatment for Chagas disease is not satisfactory, and there is a need for new treatments. In this work, we describe the optimization of a hit compound resulting from the phenotypic screen of a library of compounds against T. cruzi. The compound series was optimized to the level where it had satisfactory pharmacokinetics to allow an efficacy study in a mouse model of Chagas disease. We were able to demonstrate efficacy in this model, although further work is required to improve the potency and selectivity of this series.
- Harrison, Justin R.,Sarkar, Sandipan,Hampton, Shahienaz,Riley, Jennifer,Stojanovski, Laste,Sahlberg, Christer,Appelqvist, Pia,Erath, Jessey,Mathan, Vinodhini,Rodriguez, Ana,Kaiser, Marcel,Pacanowska, Dolores Gonzalez,Read, Kevin D.,Johansson, Nils Gunnar,Gilbert, Ian H.
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p. 3066 - 3089
(2021/06/14)
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- TREATMENT OF CHAGAS DISEASE
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The invention provides compounds of the formula: wherein L1 and L2 are independently selected from O and S; R1 is C3-C6straight or branched alkyl, C3-C7cycloalkyl, C5-C7cycloalkenyl, adamantly, phenyl or saturated heterocyclyl, any of which being optionally substituted; R2 is H, methyl or ethyl; R5 is NRxCORy, NRxRy, CH2COCH3, CH2C≡N, or a 5- or 6-membered heteroaryl group which is optionally substituted; X, Y and Z are independently N or CH; Rx is independently H or C1-C4alkyl; Ry is independently H, CrC4alkyl, phenyl or benzyl, either of which is optionally substituted; n is 0-3; salts, hydrates and N-oxides, wherein the optional substituents are further defined in the claims. The compounds have utility in the prophylaxis or treatment of trypanosomal diseases, such as T. cruzi (Chagas disease).
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Page/Page column 29
(2016/01/01)
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- PROCESS FOR PRODUCING ALIPHATIC DICARBOXYLIC ACID COMPOUND
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The present invention discloses a process for producing an aliphatic dicarboxylic acid compound, which comprises oxidizing, with a nitrite or a nitrate in the presence of trifluoroacetic acid, an alicyclic secondary alcohol compound or an alicyclic ketone compound, in each of which at least one methylene group is bonded to the carbon atom having hydroxyl group bonded thereto or the carbon atom as a member of carbonyl group, wherein the reaction is conducted in the presence of water of 5 mass % or less relative to 100 mass % of the total of the trifluoroacetic acid and the water.
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Page/Page column 6
(2008/06/13)
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- ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES
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A number of chiral secondary amines have been prepared and used as precursors to the corresponding chiral lithium amide bases.Treatment of either cis-2,6-dimethylcyclohexanone or 4-tert-butylcyclohexanone with a chiral lithium amide, followed by electrophilic quench, gives chiral products in up to 88 percent enantiomeric excess.The results with 4-tert-butylcyclohexanone are in disagreement with an earlier literature report, giving products of lower enantiomeric excess but higher optical rotation.
- Cain, Christian M.,Cousins, Richard P. C.,Coumbarides, Greg,Simpkins, Nigel S.
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p. 523 - 544
(2007/10/02)
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- Chiral products via asymmetric deprotonation of 4-tert-butylcyclohexanone using chiral lithium amide bases
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The asymmetric deprotonation of 4-tert-butylcyclohexanone using chiral lithium amide bases gives derived silyl enol ether products in up to 88% ee.
- Cousins,Simpkins
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p. 7241 - 7244
(2007/10/02)
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- ASYMMETRIZATION OF MESO-CYCLIC KETONES USING HOMOCHIRAL ACETAL TEMPLATES
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Employing the homochiral acetal template, asymmetrization of meso-substituted cyclohexanones is explored.By the use of optically-active 2,4-pentanediol as a chiral protecting group, highly diastereoselective acetal cleavage is achieved when treated with organoaluminum reagent.Dialkylaluminum amides are also effective reagents for this reaction.
- Naruse, Yuji,Yamamoto, Hisashi
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p. 6021 - 6030
(2007/10/02)
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- SYNTHESIS OF BRANCHED-CHAIN ALIPHATIC DICARBOXYLIC ACIDS.
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A technically acceptable method for the preparation of branched-chain aliphatic dicarboxylic acids containing at least 3-4 carbon atoms in the side chain has been examined. The principal physicochemical properties of the acids obtained have been determined. It has been shown that increasing the size of the alkyl substituent in the cyclohexanol has no effect on the type of dicarboxylic acid formed.
- Krestinina,Koshel',Chabutkina,Antonova,Migachev
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p. 2138 - 2142
(2007/10/02)
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