- Nickel-Catalyzed Alkoxy–Alkyl Interconversion with Alkylborane Reagents through C?O Bond Activation of Aryl and Enol Ethers
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A nickel-catalyzed alkylation of polycyclic aromatic methyl ethers as well as methyl enol ethers with B-alkyl 9-BBN and trialkylborane reagents that involves the cleavage of stable C(sp2)?OMe bonds is described. The transformation has a wide substrate scope and good chemoselectivity profile while proceeding under mild reaction conditions; it provides a versatile way to form C(sp2)?C(sp3) bonds that does not suffer from β-hydride elimination. Furthermore, a selective and sequential alkylation process by cleavage of inert C?O bonds is presented to demonstrate the advantage of this method.
- Guo, Lin,Liu, Xiangqian,Baumann, Christoph,Rueping, Magnus
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supporting information
p. 15415 - 15419
(2016/12/03)
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- Palladium-catalyzed carbonylations of aryl bromides using paraformaldehyde: Synthesis of aldehydes and esters
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Carbonylation reactions represent useful tools for organic synthesis. However, the necessity to use gaseous carbon monoxide is a disadvantage for most organic chemists. To solve this problem, novel protocols have been developed for conducting palladium-catalyzed reductive carbonylations of aryl bromides and alkoxycarbonylations using paraformaldehyde as an external CO source (CO gas free). Hence, aromatic aldehydes and esters were synthesized in moderate to good yields.
- Natte, Kishore,Dumrath, Andreas,Neumann, Helfried,Beller, Matthias
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supporting information
p. 10090 - 10094
(2015/03/31)
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- Iron-catalyzed oxidative coupling of alkylamides with arenes through oxidation of alkylamides followed by Friedel-Crafts alkylation
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FeCl3 in combination with t-BuOOt-Bu as an oxidant was found to be an efficient catalyst for oxidation of alkylamides to α-(tert-butoxy) alkylamides. FeCl2 and CuCl showed, respectively, almost the same and slightly lower activities
- Shirakawa, Eiji,Uchiyama, Nanase,Hayashi, Tamio
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experimental part
p. 25 - 34
(2011/03/22)
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- ALPHA7 NICOTINIC ACETYLCHOLINE RECEPTOR INHIBITORS
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The present invention provides compounds and compositions, methods of making them, and methods of using them to modulate α7 nicotinic acetylcholine receptors and/or to treat any of a variety of disorders, diseases, and conditions. Provided compounds can a
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Page/Page column 140
(2010/04/03)
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- SAR studies of capsazepinoid bronchodilators 3: The thiourea part (coupling region) and the 2-(4-chlorophenyl)ethyl moiety (C-region)
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Certain derivatives and analogues of capsazepine are potent in vitro inhibitors of bronchoconstriction in human small airways. During an investigation of the dependency of the potency on the structural features of the capsazepinoids in the thiourea moiety (coupling region) and the 2-(4-chlorophenyl)ethyl moiety (C-region), it was revealed that capsazepinoids with a thiourea or an amide link between the B-ring and the C-region in general have a good bronchorelaxing activity, while urea is a less attractive choice. Further, it was shown that 1,2,3,4-tetrahydroisoquinolines with a 2-(phenyl)ethyl derivative as the C-region are considerably more potent than those with an octyl group, while 2,3,4,5-tetrahydro-1H-2-benzazepines were found to be more insensitive to the nature of the C-region.
- Berglund, Magnus,Dalence-Guzman, Maria F.,Skogvall, Staffan,Sterner, Olov
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p. 2529 - 2540
(2008/09/21)
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- NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS
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The present invention provides compounds of formula (I) and compositions thereof, methods of making them, and methods of using them to modulate alpha7 nicotinic acetylcholine receptors and/or to treat any of a variety of disorders, diseases, and conditions. Provided compounds can affect, among other things, neurological, psychiatric and/or inflammatory system.
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Page/Page column 109
(2008/12/07)
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- Nickel-catalyzed cross-coupling of aryl methyl ethers with aryl boronic esters
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(Chemical Equation Presented) To C-OMe and go: The title reaction, involving cleavage of a C-OMe bond, is demonstrated for the coupling of aryl methyl ethers on fused aromatic systems, such as naphthalene and phenanthrene, as well as anisoles containing electron-withdrawing groups with a wide range of boronic esters. cod=cycloocta-1,5-diene, Cy=cyclohexyl.
- Tobisu, Mamoru,Shimasaki, Toshiaki,Chatani, Naoto
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experimental part
p. 4866 - 4869
(2009/02/08)
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- MODULATORS OF ALPHA7 NICOTINIC ACETYLCHOLINE RECEPTORS AND THERAPEUTIC USES THEREOF
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Compounds with α7 nicotinic acetylcholine receptor (α7 nAChR) agonistic activity, processes for their preparation, pharmaceutical compositions containing the same and the use thereof for the treatment of neurological and psychiatric diseases.
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Page/Page column 76
(2010/11/28)
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- Substituted naphthoic acid derivatives useful in the treatment of insulin resistance and hyperglycemia
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This invention provides compounds of Formula I having the structure wherein: R1 is hydroxyl, alkoxy of 1-4 carbons or —O(CH2)nX; n is an integer of 1-3; X is CONHR6 or CO2R6; R2
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Page/Page column 6
(2008/06/13)
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- NAPTHTHALENE DERIVATIVES WHICH INHIBIT THE CYTOKINE OR BIOLOGICAL ACTIVITY OF MACROPHAGE MIGRATION INHIBITORY FACTOR (MIF)
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Where Y, R1-R8 and R101-R108 are as defined in the specification. Compounds of formula (II) and methods of inhibiting the cytokine or biological activity of Macrophage Migrating Inhibitory Factor (MIF) comprising contacting MIF with a compound of formula (I) are provided. The invention also relates to methods of treating diseases or conditions where MIF cytokine or biological activity is implicated comprising administration of compounds of formula (I), either alone or as part of a combination therapy.
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- Solvolyses of naphthoyl chlorides. Solvent effect and Grunwald-Winstein correlation analyses with YxBnCl scales
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The solvolyses of 1-naphthoyl (2), 2-naphthoyl (3), 4-methyl-1-naphthoyl (4) and 6-methoxy-2-naphthoyl (5) chlorides in a variety of solvents were studied, and correlation analyses by using the single- and dual-parameter Grunwald-Winstein equations were examined. An excellent linear relationship (R = 0.995) for 4, log (k/k0) = 0.733YxBnCl + 0.269NOTs, was observed. An SN1-like mechanism with decreasing extent of nucleophilic solvent participation was found in the solvolysis of 2 and 4.2-Naphthoyl chloride is likely to have a mechanism at the borderline of SN1-like dissociation and an addition-elimination process. 6-Methoxy-2-naphthoyl chloride shows more SN1-like character than 3 and is associated with nucleophilic solvent intervention more pronounced than that for 2 and 4. The applicability and the advantages of using the YxBnCl scale for different types of substrates are discussed. Copyright
- Liu, Kwang-Ting,Hwang, Patty Y.-H.,Chen, Hun-I.
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p. 750 - 757
(2007/10/03)
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- Process for the preparation of aromatic methoxycarboxylic acid methyl esters
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In a process, improved in respect of yield, purity and simple procedure, for the preparation of aromatic methoxycarboxylic acid methyl esters by methylation of the corresponding aromatic hydroxycarboxylic acids with dimethyl sulfate in the presence of water and a base, a procedure is followed in which the water, base and aromatic hydroxycarboxylic acid are initially introduced into the reaction vessel, 1 to 2.5 times the molar amount of dimethyl sulfate (based on the methylatable hydroxyl and carboxyl groups) is metered in and, during this procedure, the pH of the reaction mixture is controlled by addition of an aqueous base in finely divided form.
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- Sequential Acetalization-Pyrolysis of α-Acetylcinnamates and α-Acetylbenzalacetones. A Method for the Generation of 2-Carbonyl-Subsituted Naphthalenes
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Substituted 2-acetonaphthones and 2-naphthoate methyl esters can be generated from benzaldehydes in a sequence of three reaction steps.Knoevenagel condensation of a benzaldehyde with 2,4-pentandione of methyl acetoacetate yields α-carbonyl-substituted benzalacetones.The α-carbonyl-substituted benzalacetones are then cyclized to generate the α-carbonyl-substituted naphthalenes by a sequential acetalization with trimethyl orthoformate followed by subsequent pyrolysis of the dimethyl acetal either in the vapor phase at 475 deg C or by being heated in boiling 1-methylnaphthalene. 2-Acetonaphthones are obtained when 2,4-pentanedione is used and 2-naphthoate methyl esters are obtained from methyl acetoacetate.
- Zoeller, Joseph R.,Sumner, Charles E.
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p. 319 - 324
(2007/10/02)
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- Analogues of clofibrate and clobuzarit containing fluorine in the side chains
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A series of analogues of clofibrate and 2-[4-(4-chlorophenyl)phenylmethoxy]-2-methylpropionic acid (clobuzarit) has been prepared by replacing the methyl groups by trifluoromethyl groups and changing the aromatic moiety. The activity of these compounds has been assayed on the plasma levels of cholesterol, Total Esterified Fatty Acids (T.E.F.A.) and fibrinogen in rats. It appears that derivatives of the first series which contain only one trifluoromethyl group are hypocholesterolaemic and that many mono- of bis- trifluoromethyl derivatives of the second series lower the levels of both cholesterol and T.E.F.A. in contrast to clobuzarit.
- Haydock,Mulholland,Telford,et al.
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p. 205 - 214
(2007/10/02)
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