- Radical hydroxymethylation of alkyl iodides using formaldehyde as a C1 synthon
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Radical hydroxymethylation using formaldehyde as a C1 synthon is challenging due to the reversible and endothermic nature of the addition process. Here we report a strategy that couples alkyl iodide building blocks with formaldehyde through the use of photocatalysis and a phosphine additive. Halogen-atom transfer (XAT) from α-aminoalkyl radicals is leveraged to convert the iodide into the corresponding open-shell species, while its following addition to formaldehyde is rendered irreversible by trapping the transient O-radical with PPh3. This event delivers a phosphoranyl radical that re-generates the alkyl radical and provides the hydroxymethylated product.
- Caiger, Lewis,Constantin, Timothée,Douglas, James J.,Juliá, Fabio,Leonori, Daniele,Sheikh, Nadeem S.,Sinton, Conar
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p. 10448 - 10454
(2021/08/20)
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- PYRAZOLE AMIDE DERIVATIVE
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The present invention relates to a novel compound having a function of inhibiting RORγ activity. The present invention also relates to pharmaceutical composition comprising the compound, a use of the compound in treating or preventing autoimmune diseases, inflammatory diseases, metabolic diseases, or cancer diseases.
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Page/Page column 189
(2015/09/28)
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- Synthesis of epibatidine analogues having a 2-substituted 2-azabicyclo[2.2.2]octane skeleton
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The synthesis of 1-cyano-2-aza-[2.2.2]bicyclooctanes has been studied using the dynamic cyanide addition to cyclohexanone derivatives. These compounds were further elaborated into a new class of epibatidine derivatives from which a number of examples were
- Wauters, Iris,De Blieck, Ann,Muylaert, Koen,Heugebaert, Thomas S. A.,Stevens, Christian V.
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p. 1296 - 1304
(2014/03/21)
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- Synthesis of Epibatidine Analogues Having a 2-Substituted 2-Azabicyclo[2.2.2]octane Skeleton
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The synthesis of 1-cyano-2-aza-[2.2.2]bicyclooctanes has been studied using the dynamic cyanide addition to cyclohexanone derivatives. These compounds were further elaborated into a new class of epibatidine derivatives from which a number of examples were
- Wauters, Iris,De Blieck, Ann,Muylaert, Koen,Heugebaert, Thomas S. A.,Stevens, Christian V.
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p. 1296 - 1304
(2015/10/05)
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- Control of transient aluminum-aminals for masking and unmasking reactive carbonyl groups
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A new reagent, the dimethylaluminum N,O-dimethylhydroxylamine complex, is effective at masking reactive carbonyl groups in situ from nucleophilic addition. This reagent allows chemoselective addition of reducing reagents, Grignard reagents, organolithiums, Wittig reagents, and enolates into substrates with multiple carbonyl groups. Moreover, the trapped carbonyl group, a stable aminal, can be unmasked in situ for additional synthetic manipulations.
- Barrios, Francis J.,Springer, Brannon C.,Colby, David A.
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supporting information
p. 3082 - 3085
(2013/07/26)
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- CYCLOHEXYL-AZETIDINYL ANTAGONISTS OF CCR2
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The present invention comprises compounds of Formula (I). wherein: R1, R2, X, and Z are as defined in the specification. The invention also comprises a method of preventing, treating or ameliorating a syndrome, disorder or disease, wherein said syndrome, disorder or disease is type II diabetes, obesity and asthma. The invention also comprises a method of inhibiting CCR2 activity in a mammal by administration of a therapeutically effective amount of at least one compound of Formula (I).
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Page/Page column 62
(2012/01/03)
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- BRIDGED COMPOUNDS AS HIV INTEGRASE INHIBITORS
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Compounds of Formula I are inhibitors of HIV integrase and inhibitors of HIV replication: the asterisk * in Q denotes the point of attachment to the rest of the compound; and n, L1, L2, X1, X2, χ3, Y, Z, R1, Rs
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Page/Page column 58
(2010/08/09)
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- One-pot synthesis of symmetrical 1,3-diarylureas or substituted benzamides directly from benzylic primary alcohols and effective oxidation of secondary alcohols to ketones using phenyliodine diacetate in combination with sodium azide
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Benzylic primary alcohols can be directly converted into symmetrical 1,3-diarylureas or substituted benzamides via an one-pot oxidative reaction using the combined reagent of phenyliodine diacetate and sodium azide. This new reaction constitutes a step-economical way to prepare symmetric 1,3-diarylureas or substituted benzamides depending upon the substituents on the phenyl rings of starting alcohols. The sodium acetate generated in situ from the ligand exchange between phenyliodine diacetate and sodium azide plays the pivotal role in the formation of 1,3-diarylureas. In addition, it is also found that various secondary alcohols can be readily oxidized to their corresponding ketones in excellent yields using the same reagent system of phenyliodine diacetate and sodium azide. Generally, secondary alcohols are preferentially oxidized to the corresponding ketones in the presence of primary ones with the limited amounts of phenyliodine diacetate and sodium azide.
- Li, Xiao-Qiang,Wang, Wei-Kun,Han, Yi-Xin,Zhang, Chi
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experimental part
p. 2588 - 2598
(2010/12/25)
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- HIV Integrase Inhibitors
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The disclosure generally relates to the novel compounds of formula I, including their salts, which inhibit HIV integrase and prevent viral integration into human DNA. This action makes the compounds useful for treating HIV infection and AIDS. The invention also encompasses pharmaceutical compositions and methods for treating those infected with HIV.
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Page/Page column 65
(2009/10/17)
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- Conformationally restricted nonchiral pipecolic acid analogues
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(Chemical Equation Presented) Practical syntheses of 2-azabicyclo[3.1.1] heptane-1-carboxylic (2,4-methanopipecolic), 2-azabicyclo [2.2.2]octane-1- carboxylic (2,5-ethanopipecolic), and 9-azabicyclo[3.3.1]nonane-1-carboxylic (2,6-propanopipecolic) acids a
- Radchenko, Dmytro S.,Kopylova, Nataliya,Grygorenko, Oleksandr O.,Komarov, Igor V.
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scheme or table
p. 5541 - 5544
(2009/12/04)
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- Novel Angiogenesis inhibitors and pharmaceutical/cosmetic applications thereof
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Novel derivatives of fumagalone have the general formula (I): and are useful angiogenes is inhibitors; these can be formulated into pharmaceutical compositions suited for human or veterinary medicine, or can be formulated into cosmetic compositions.
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Page/Page column 7; sheet 2
(2010/11/27)
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- New bioorganic reagents: Evolved cyclohexanone monooxygenase - Why is it more selective?
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Four mutants of the cyclohexanone monooxygenase (CHMO) evolved as catalysts for Baeyer-Villiger oxidation of 4-hydroxycyclohexanone were investigated as catalysts for a variety of 4-substituted and 4,4-disubstituted cyclohexanones. Several excellent catalytic matches (mutant/substrate) were identified. The most important, however, is the finding that, in a number of cases, a mutant with a single exchange, Phe432Ser, was shown to be as robust and more selective as a catalyst than the wild-type CHMO. All biotransformations were performed on a laboratory scale, allowing full characterization of the products. The absolute configurations of two products were established. A model suggesting a possible role of the 432 serine residue in enantioselectivity control is proposed.
- Kayser, Margaret M.,Clouthier, Christopher M.
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p. 8424 - 8430
(2007/10/03)
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- METHODS OF RADIOFLUORINATION OF BIOLOGICALLY ACTIVE VECTORS
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The invention relates to conjugates of formula (V) or (VI): wherein X is -CO-NH-, -NH-, -O-, -NHCONH-, or -NHCSNH-; their use as radiopharmaceuticals, processes for their preparation, and synthetic intermediates used in such processes.
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Page/Page column 25
(2010/02/08)
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- Cr(III) or Ce(IV) Impregnated Perfluorinated Resin-Sulfonic Acid Catalyst for the Oxidation of Alcohols
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Sereval polymer supported catalysts are prepared by treatment of Nafion 551 (abbreviated NAFK below) with metal salts.Cr/NAFK and Ce/NAFK found to be effective catalysts for the dehydrogenative oxidation of alcohols to the corresponding ketones by means of t-butyl hydroperoxide.Selective oxidation of secondary alcohols in the presence of primary ones was performed using a Ce/NAFK-NaBrO3 system.
- Kanemoto, Shigekazu,Saimoto, Hiroyuki,Oshima, Koichiro,Utimoto, Kiitiro,Nozaki, Hitosi
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p. 519 - 523
(2007/10/02)
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- Cerium or Ruthenium Catalyzed Oxidation of Alcohols to Carbonyl Compounds by Means of Sodium Bromate
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Sodium bromate has been found to be effective oxidant for oxidation of alcohols in the presence of cerium or ruthenium compounds in biphase reaction.Selective oxidation of secondary alcohols was performed in the presence of primary ones using cerium(IV) ammonium nitrate (CAN) or cerium(IV) sulfate (CS) as catalyst.For instance, treatment of 1,10-undecanediol with CS/NaBrO3 provided 11-hydroxy-2-undecanone in 82percent yield.Ruthenium catalyzed biphase oxidation of alcohols with sodium bromate provided the corresponding aldehydes or ketones in good to excellent yields.
- Kanemoto, Shigekazu,Tomioka, Hiroki,Oshima, Koichiro,Nozaki, Hitosi
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p. 105 - 108
(2007/10/02)
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- Perfluorocarbon polymer oxidation catalyst and preparation of carbonyl compound
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This invention deals with the use of a perfluorocarbon polymer oxidation catalyst consisting of a perfluorocarbon main chain and a side chain constructed from structural units of chromium (III) difluoromethylene sulfonate or cerium (IV) difluoromethylene sulfonate in a method of preparing a carbonyl compound through an oxidation of an alcohol.
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- A New Synthesis of Bicycloocta-2,4-diene and Its Cycloaddition Reactions with Dienophiles.
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Bicycloocta-2,4-diene (4) has been synthesized by a new, nine-step route, starting from 2--1,3-butadiene and acrolein.Diene (4) proved almost as unreactive toward Diels-Alder cycloadditions as the previously studied 7,7-dimethy
- Yin, Tyze-Kuan,Lee, Jon Gun,Borden, Weston Thatcher
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p. 531 - 534
(2007/10/02)
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- Cr(III) OR Ce(IV) IMPREGNATED PERFLUORINATED RESIN-SULFONIC ACID CATALYSTS FOR THE OXIDATION OF ALCOHOLS
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Several polymer supported catalysts are prepared by treatment of NafionR 511 (abbreviated as NAFK below) with metal salts and found to be effective in promoting the dehydrogenative oxidation of alcohols with tBuOOH.
- Kanemoto, Sigekazu,Saimoto, Hiroyuki,Oshima, Koichiro,Nozaki, Hitosi
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p. 3317 - 3320
(2007/10/02)
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- 2-Cyanoaziridinyl-(1)-2-substituted-aziridinyl-(1)-methanes
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A 2-cyanoaziridinyl-(1)-2-substituted-aziridinyl-(1)-methane STR1 wherein R is a nitrile or carbamoyl group, and R1 and R2 each independently is a hydrogen atom, an aliphatic hydrocarbon radical containing up to 10 carbon atoms optionally substituted by hydroxyl, alkoxy, amino, alkylamino, dialkylamino, alkoxycarbonyl, cyano, 1, 2 or 3 halogens, cycloalkyl, phenyl or phenoxy; nitrile, carboxyl, alkoxycarbonyl or optionally hydrogenated monocyclic heteroaryl or phenyl optionally substituted by alkyl, alkoxy, hydroxy, alkoxcarbonyl, dialkylamino, alkylthio, trifluoromethyl, nitro, carbamoyl, nitrile, sulphonamido, hydroxyalkyl, methylenedioxy, or halogen; or R1 and R2, together with the carbon atom to which they are attached, form a ring containing up to 8 ring members of which at least one may be oxygen, sulphur, SO, SO2 NH, N-alkyl, N-acyl or N-alkoxycarbonylalkyl, and which can be substituted by alkyl, alkoxy, hydroxyl, alkylenedioxy, alkoxycarbonyl, hydroxyalkyl, alkoxycarbonylalkyl, dialkylamino, oxo or 2-cyanoaziridino groups, or can be fused to 1 or 2 benzene rings or can be bridged by alkylene radicals containing up to 3 carbon atoms. The compounds are characterized by cytostatic and immune response-stimulating activity.
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- CERIUM CATALYZED SELECTIVE OXIDATION OF SECONDARY ALCOHOLS IN THE PRESENCE OF PRIMARY ONES
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The combination of (NH4)2Ce(NO3)6-NaBrO3 or Ce(SO4)2.2H2SO4-NaBrO3 has been found to be effective for the title selective oxidation.
- Tomioka, Hiroki,Oshima, Koichiro,Nozaki, Hitosi
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p. 539 - 542
(2007/10/02)
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