- Mn/Cu catalyzed addition of arylboronic acid to nitriles: Direct synthesis of arylketones
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A direct and efficient synthesis of arylketones via arylboronic acid addition to nitriles in presence of inexpensive Mn/Cu catalytic system is reported. The use of non-precious Mn and Cu salts has been found to be highly advantageous both in terms of accessibility as well as cost effectiveness. A series of arylboronic acids as well as nitriles were used to synthesize a variety of symmetrical and unsymmetrical arylketones. Based on the literature studies, the reaction mechanism is anticipated to go through an aryl radical intermediate which reacted with the copper activated nitrile to give the desired arylketones after the hydrolysis of the imine intermediate.
- Moustafa, Dina,Sweet, Chelsea,Lim, Hyun,Calalpa, Brenda,Kaur, Parminder
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Read Online
- NOVEL DIHYDROPYRIMIDIN-2(1H)-ONE COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS
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The present invention is directed to novel dihydropyrimidin-2(1H)-one compounds useful as S-nitrosoglutathione reductase (GSNOR) inhibitors, pharmaceutical compositions comprising such compounds, and methods of making and using the same.
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Page/Page column 146-147
(2011/04/24)
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- Intramolecular cation-π interactions control the conformation of nonrestricted (phenylalkyl)pyridines
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NOEsy and fluorescence spectroscopy reveal that conversion of conformationally flexible (phenylalkyl)pyridines into their corresponding N-methyl-pyridinium iodides results in intramolecular π-stacking. The Royal Society of Chemistry.
- Richter, Isabella,Minari, Jusaku,Axe, Philip,Lowe, John P.,James, Tony D.,Sakurai, Kazuo,Bull, Steven D.,Fossey, John S.
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p. 1082 - 1084
(2008/12/20)
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- An improved and practical procedure for the synthesis of substituted phenylacetylpyridines
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A general procedure for the synthesis of substituted phenylacetylpyridines in excellent yields is described using a Horner-Emmons condensation between α-aminoalkylphosphonates of pyridinecarboxaldehydes and benzaldehydes with cesium carbonate at room temperature.
- Journet, Michel,Cai, Dongwei,Larsen, Robert D.,Reider, Paul J.
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p. 1717 - 1720
(2007/10/03)
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- Proton activating factors and keto-enol-zwitterion tautomerism of 2-, 3- And 4-phenylacetylpyridines
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Equilibrium constants for keto-enol tautomerism of 2-, 3- and 4-phenylacetylpyridines in aqueous solution at 25°C have been measured as pKTE = 3.35, 4.2 and 3.1 respectively (KTE = [enol]/[ketone], PKTE = -log KTE). Corresponding values for the N-protonated ketones are 1.64, 2.80 and 1.54. These enol contents are consistently higher than those of the isomeric phenacylpyridines, except in the case of the (unprotonated) 2-isomer where the greater enol content of the latter (pKTE = 2.0) can be attributed to more effective stabilization by hydrogen-bonding to the pyridyl nitrogen in a six- than five-membered ring. The tautomeric constants were obtained by combining rate constants for enolisation, measured by halogen trapping, with rate constants for relaxation of the enol tautomer (generated by quenching the enolate anion into acid or acidic buffers) to its more stable keto isomer. Approximate tautomeric constants for zwitterion formation (pKTZ = 4.6, 7.4 and 6.1 for 2-, 3- and 4-isomers respectively) are inferred from measurements of ionisation constants and keto-enol tautomeric constants for N-methylated ketones by taking the N-methylated enolate anions as models for the zwitterions and correcting for the substituent effect of the methyl group. The tautomerism is discussed in terms of the relationship pKT = ΔpKab + log PAF which dissects tautomeric constants into contributions from (a) a difference in pKas of non-interacting acidic and basic tautomeric sites (ΔpKab) and (b) a mutual stabilisation of these sites from conjugative, inductive or hydrogen-bonded interactions between them. This stabilisation is described by a proton activating factor (PAF) measuring the effect of protonation at one tautomeric site upon the ionisation constant at the other.
- McCann, Geraldine M.,More O'Ferrall, Rory A.,Walsh, Sinead M.
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p. 2761 - 2772
(2007/10/03)
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- Substituted (1,2-Diarylethyl)amide Acyl-CoA:Cholesterol Acyltransferase Inhibitors: Effect of Polar Groups on in Vitro and in Vivo Activity
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Substituted (1,2-diarylethyl)amides have been prepared and evaluated for their ability to inhibit microsomal acyl-CoA:cholesterol acyltransferase activity in vitro and to lower hepatic cholesteryl ester content in vivo in a cholesterol-fed hamster.Simple unsubstituted (diarylethyl)amides were potent inhibitors in vitro but showed poor activity in vivo.Introduction of polar groups at specific locations on the diarylethylamine moiety decreased in vitro activity but increased in vivo activity.Both effects were highly structure dependent, suggesting specific interactions which were mediating activity in each model.Optimization of these opposing effects led to compounds which were potent in both models.
- Clader, John W.,Berger, Joel G.,Burrier, Robert E.,Davis, Harry R.,Domalski, Martin,et al.
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p. 1600 - 1607
(2007/10/02)
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- The anion of 4-dimethoxymethylpyridine. A convenient synthesis of some 4-pyridyl ketones
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n-Butyllithium at -78°C abstracts the methine proton from 4-dimethoxymethylpyridine. The anion reacts efficiently with electrophiles. Simple ketal products can be readily hydrolysed to 4-pyridyl ketones.
- Sheldrake
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p. 1967 - 1971
(2007/10/02)
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- Inhibitors of acyl-coenzyme A: cholesterol acyl transferase
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Amides of the formula STR1 wherein R1 and R2 are independently heteroaryl, X-substituted heteroaryl, X-substituted phenyl, N-substituted triazinyl or N-substituted imidazolyl; and in addition, one of R1 and R2 can be as defined above and the other can be phenyl; R3 is an alkyl chain of 2 to 25 carbon atoms, saturated or unsaturated; an alkyl chain as defined substituted by one or more substituents selected from the group consisting of phenyl, X-substituted phenyl, heteroaryl and X-substituted heteroaryl; an alkyl chain as defined interrupted by one or more groups independently selected from the group consisting of --O--, --S--, --SO--, --SO2 --, --NH--, --N(lower alkyl)--, --C(O)--, phenylene, X-substituted phenylene, heteroarylene and X-substituted heteroarylene; or an interrupted alkyl chain as defined substituted by one or more substituents selected from the group consisting of phenyl, X-substituted phenyl, heteroaryl and X-substituted heteroaryl; R4 is hydrogen, lower alkyl, phenyl, X-substituted phenyl, heteroaryl or X-substituted heteroaryl; or a pharmaceutically acceptable salt thereof, useful as inhibitors of acyl-coenzyme A:cholesterol acyl transferase and therefore in the treatment of atherosclerosis are disclosed.
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- Equilibrium and Kinetic Acidities of Benzylic Ketones. Application of the Marcus Equation to the Deprotonation of Carbon Acids
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Equilibrium constants and rates of ketone-enolate ion equilibration have been measured for the deprotonation of eight 3-(X-phenylacetyl)pyridines 1 (pKa 13.2 for X = H), ten 4-(X-phenylacetyl)pyridines 2 (pKa 12.2 for X = H), nine 1-
- Bunting, John W.,Stefanides, Dimitrios
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p. 4008 - 4017
(2007/10/02)
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- Synthese von Pyridylphenyl-imidazothiazolen
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The synthesis of the isomeric 6(5)-phenyl-5(6)-pyridyl-2,3-dihydroimidazothiazoles are described.Only the synthesis of 5-phenyl-6-(2-pyridyl)-2,3-dihydroimidazothiazole failed.
- Klose, Walter,Schwarz, Katica
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p. 669 - 671
(2007/10/02)
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- 1-Phenylisoquinoline derivatives, pharmaceutical products containing these compounds and their use
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1-Phenylisoquinoline derivatives of the general formula I STR1 and a process for their preparation are described. They act on the central nervous system, in particular as antidepressants.
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