Phenyl pyridyl ketone

Scheme 14.13 Proposed mechanism for the hydrogenation of phenyl acetylene by [Pd(methyl 2-pyridyl ketone thiosemicarba-zonato)Cl] (29a).

The (E)-alkene (74) is formed from Wittig reaction of the corresponding phenyl 3-pyridyl ketone the stereochemical preference is determined by an interaction (either hydrogen bonding or salt bridging) between the carboxylic acid chain being introduced and the amide tether provided by the reactant." ... 

The preferential formation of ( )-alkene on Wittig reaction of phenyl 3-pyridyl ketones (bearing an oxazole carboxamide group at the / -position of the phenyl ring) with Ph3P=CH(CH2)4C02 K+ has been attributed to interaction between the amide (rather than oxazole) moiety and the carboxyl terminus during oxaphosphetane formation. ... 

Several related examples of transition metal-catalyzed addition of C-H bonds in ketones to olefins have been reported (Table 2) [11-14]. The alkylation of diterpenoid 6 with olefins giving 7 proceeds with the aid of Ru(H)2(CO)(PPh3)3 (A) or Ru(CO)2(PPh3)3 (B) as catalyst [11], Ruthenium complex C, Ru(H)2(H2)(CO) (PCy3)2, has catalytic activity in the reaction of benzophenone with ethylene at room temperature [12]. The alkylation of phenyl 3-pyridyl ketone 8 proceeds with A as catalyst [13], Alkylation occurs selectively at the pyridine ring. Application of this C-H/olefin coupling to polymer chemistry using ce,co-dienes such as 1,1,3,3-tetramethyl-l,3-divinyldisiloxane 11 has been reported [14]. 

The yeast-induced reduction of (5e) —> (6e), (R = substituted phenyls, R = Me) is one of the very first preparative-scale alcohol dehydrogenase catalyzed reactions to have been reported. While the transformations of (5a-j) demonstrate that broad structural mlerances are possible in the substrate ketones, the enzymes are sometimes very discriminating. For example, while the BY-catalyzed reductions of the 2-, 3- and 4-substituted pyridyl ketones (5g) proceed smoothly with high stereospecificitythe analogous furanyl and thiophenyl ketones give virtually racemic product alcohols, and 2-acetylpyrrole is not a substrate at all. ... 

Diaryl ketones can also be prepared by coupling aryl iodides with phenylboronic acid (12-28), in the presence of CO and a palladium catalyst.This reaction has been extended to heteroaromatic systems, with the preparation of phenyl 4-pyridyl ketone from phenylboronic acid and 4-iodopyridine. 2-Bromopyridine as coupled with phenylboronic acid, CO and a palladium catalyst to give phenyl... 

Indirect oxidation with tris-(4-bromophenyl)amine or 2,3-dihydro-2,2-dimethylphe-nothiazine-6(l/7)-one transforms formazane to tetrazolium, semicarbazones to 2-amino-1,3,4-oxadiazoles, benzaldehyde 2-pyridylhydrazones to 5-triazolo[4,3-a]pyridinium compounds, and phenyl 2-pyridyl ketone phenylhydrazone to 1/7-1,2,3-triazolo[3,4-a]-pyridi-nium compounds [123]. 

The synthesis of the 3- and 4- pyridyl Grignard reagents (120) and (121) has been achieved by reaction of the corresponding phenyl pyridyl sulphoxide with phenyl magnesium bromide (Scheme 34). The pyridyl Grignards were trapped with aldehydes and ketones, and the... 

It is synthesized by Grignard reaction of phenyl-2-pyridyl ketone with phenyl magnesium bromide followed by catalytic reduction to get the official compound. 

Phenyl 2-pyridyl ketone (293) underwent Wittig-Homer reactions to give the unsaturated ester (294) and the acrylonitrile (296). However, neither... 

A mixture of 4.5 g 2-benzyl-phenyl 2-pyridyl ketone (0.017 mol), 25 mL 48% hydro-bromic acid, and 50 mL glacial acetic acid was reflux for 52 h. The solution was neutralized with dilute NaOH, and the resultant precipitate was collected, washed with water, and dried 3.9 g of 9-(2-pyridyl)anthracene was obtained, in a yield of 92%. The product was recrystallized from a mixture of ethanol and methanol to afford light yellow-green crystals, m.p. 163-165°C. 

Arnino-3-hydroxy-5-hydroxymethylpyiidine dihydrochloiide is prepared by hydrogenation of the oxime of 4-formyl-3-hydroxyl-5-hydroxymethylpyridine in aqueous hydrochloric acid over palladium-charcoal. 2-(ci -Aminobenzyl)pyridine is obtained by the reduction of phenyl 2-pyridyl ketone oxime with zinc dust and acetic acid. ... 

Another method of preparing aminoalkynylpyridines involves the reaction of lithium alkynes with pyridyl ketones. Thus, 4-diethylamino-1-phenyl-1-(2-pyridyl)-2-butyn-l-ol (IX-2S4) is obtained by the reaction of lithium amide with diethylamino-2-propyne followed by 2-benzoylpyridine. Similarly, the use of 3-... 

Vingiello and Schlechter described the Bradsher cyclodehydration of o-benzylphenyl ketone containing a strongly basic group in the presence of either phenyl acid phosphate or benzenesulfonic acid. 4-Benzylphenyl pyridyl ketone (18) underwent cyclization in the presence of phenyl acid... 

FhenftUiyiHZ-t dy. fceton 81, 333. [2.4-I imethyl-phenyl]>d.pyridyl-keton 811311. 

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