29955-23-5Relevant academic research and scientific papers
Transition-Metal-Free Intermolecular α-Arylation of Ketones via Enolonium Species
Maksymenko, Shimon,Parida, Keshaba N.,Pathe, Gulab K.,More, Atul A.,Lipisa, Yuriy B.,Szpilman, Alex M.
supporting information, p. 6312 - 6315 (2017/12/08)
Herein it is shown, for the first time, that enolonium species are powerful electrophiles capable of reacting with aromatic compounds in an intermolecular manner to afford α-arylated ketones. The reaction is compatible with a variety of functional groups, is of wide scope with respect to aromatic compounds and ketone, and even works for polymerization-prone substrates such as substituted pyrroles, thiophenes, and furans. Only 1.6 to 5 equiv of the commodity aromatic substrates is needed.
Cyclic α-Alkoxyphosphonium Salts from (2-(Diphenylphosphino)phenyl)methanol and Aldehydes and Their Application in Synthesis of Vinyl Ethers and Ketones via Wittig Olefination
Huang, Wenhua,Rong, Hong-Ying,Xu, Jie
, p. 6628 - 6638 (2015/10/06)
Cyclic α-alkoxyphosphonium salts have been synthesized from (2-(diphenylphosphino)phenyl)methanol and aldehydes in 36-89% yields. These phosphonium salts are bench-stable solids and undergo Wittig olefination with aldehydes under basic conditions (K2CO3 or t-BuOK) to form benzylic vinyl ethers, which are readily hydrolyzed to 1,2-disubstituted ethanones under acidic conditions. The formation mechanism of these phosphonium salts via hemiacetal is also proposed.
NOVEL DIHYDROPYRIMIDIN-2(1H)-ONE COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS
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Page/Page column 138, (2011/04/24)
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.
Towards a facile synthesis of triarylethanones: Palladium-catalyzed arylation of ketone enolates under homogeneous and heterogeneous conditions
Churruca, Fátima,SanMartin, Raul,Carril, Mónica,Tellitu, Imanol,Domínguez, Esther
, p. 2393 - 2408 (2007/10/03)
The palladium-catalyzed regioselective α-monoarylation of deoxybenzoins and α,α-diarylation of acetophenones provides general, efficient access to 1,2,2-triarylethanones. After a comprehensive search for suitable experimental conditions to optimize such transformations, both reactions are alternatively conducted by means of either commercially available polymer-anchored catalysts or a very simple homogeneous catalytic system, thus avoiding the use of complex ligands. In addition, the synthesis of deoxybenzoins employing polymer-supported fibrous palladium catalysts is reported for the first time, and the excellent catalyst recycling properties suggest applicability to industrial purposes.
Two general routes to 1,4-disubstituted-2,3,4,5-tetrahydro- 1H-3-benzazepines.
Gerritz,Smith,Nanthakumar,Uehling,Cobb
, p. 4099 - 4102 (2007/10/03)
[structure] Two general routes to 1,4-disubstituted-2,3,4, 5-tetrahydro-1H-3-benzazepines are described. Both routes utilize an appropriately functionalized phenethylamino alcohol as the penultimate intermediate: the first route makes use of the reductive amination of a benzyl alkyl ketone with alpha-(aminomethyl)benzyl alcohol, while the second route utilizes the addition of a Grignard reagent to the oxazolidine derived from a substitued phenylacetaldehyde and alpha-(methylaminomethyl)benzyl alcohol. In all cases studied, the cis-1,4-disubstituted-2,3,4, 5-tetrahydro-1H-3-benzazepine was obtained as the major product.
Substituted (1,2-Diarylethyl)amide Acyl-CoA:Cholesterol Acyltransferase Inhibitors: Effect of Polar Groups on in Vitro and in Vivo Activity
Clader, John W.,Berger, Joel G.,Burrier, Robert E.,Davis, Harry R.,Domalski, Martin,et al.
, p. 1600 - 1607 (2007/10/02)
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.
N-acyl-tetrahydroisoquinolines as inhibitors of acyl-coenzyme a:cholesterol acyl transferase
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, (2008/06/13)
N-acyltetrahydroisoquinolines including novel compounds of the formula STR1 wherein R1 is a C10-C25 alkyl chain; a substituted C10-C25 alkyl chain; an interrupted C10-C25 alkyl chain; a substituted interrupted C10-C25 alkyl chain; diphenylamino
A Modified Bischler-Napieralski Procedure for the Synthesis of 3-Aryl-3,4-dihydroisoquinolines
Larsen, Robert D.,Reamer, Robert A.,Corley, Edward G.,Davis, Paul,Grabowski, Edward J. J.,et al.
, p. 6034 - 6038 (2007/10/02)
A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented.Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3.Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields.The method is also highly effective with (2-phenylethyl)amides.
SYNTHESIS AND PROPERTIES OF HETEROCYCLIC CARBOXONIUM SYSTEMS VII.* SYNTHESIS AND PROPERTIES OF 2-BENZYL-SUBSTITUTED 1,3-DIOXOLANIUM SALTS
Mezheritskaya, L. V.,Matsovskaya, E. S.,Dorofeenko, G. N.
, p. 174 - 178 (2007/10/02)
A method was developed for the synthesis of 2-benzyl-substituted 1,3-dioxolanium salts by acylation of pinacone by arylacetyl chlorides in the presence of silver perchlorate or of boron trifluoride etherate.The reactions of the salts with various aldehydes, acetals, ketals, ethyl orthoformate, and organomagnesium compounds were investigated.
