4789-06-4

Usage

Uses

Used in Organic Synthesis:
(1-oxido-2-pyridinyl)(phenyl)methanone serves as a key building block in organic synthesis, where it is utilized for the construction of more complex organic molecules with specific properties. Its unique structure allows for versatile chemical reactions, making it a valuable component in the synthesis of a wide range of compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (1-oxido-2-pyridinyl)(phenyl)methanone is employed as a starting material for the development of new pharmaceuticals. Its reactivity and structural features make it suitable for the design and synthesis of bioactive molecules with potential therapeutic applications.
Used in Drug Development:
(1-oxido-2-pyridinyl)(phenyl)methanone is being studied for its potential pharmacological activities, with ongoing research exploring its use in drug development. Its unique chemical properties and reactivity make it a promising candidate for the creation of novel therapeutic agents that could address various medical conditions.

Upstream product

• 694-59-7 pyridine N-oxide 
• 611-73-4 Benzoylformic acid 
• 110-86-1 pyridine 
• 530-48-3 1,1-Diphenylethylene 
• 108-86-1 bromobenzene 
• 20469-72-1 phenylboronic acid-d₂ 
• 98-80-6 phenylboronic acid 
• 108-88-3 toluene 
• 20531-86-6 2-benzylpyridine-N-oxide 
• 100-44-7 benzyl chloride 
• 100-51-6 benzyl alcohol 
• 91-02-1 phenyl(pyridin-2-yl)methanone 

Downstream Products

• 5583-33-5 (S)-(+)-α-phenyl-2-pyridylmethanol 
• 91-02-1 phenyl(pyridin-2-yl)methanone 
• 31796-72-2 phenyl(2-pyridinyl)methanol 
• 80099-99-6 (6-chlorolpyridin-2-yl)(phenyl)methanone 
• 19125-73-6 4-deuterated-N,N-dimethylaniline 
• 613-37-6 4-methoxylbiphenyl 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 1563017-45-7 (4-methoxyphenyl)(1-oxido-2-pyridinyl)methanone 

Relevant academic research and scientific papers

Enantioselective addition of nitromethane to 2-acylpyridine N -Oxides. Expanding the generation of quaternary stereocenters with the henry reaction

The direct asymmetric Henry reaction with prochiral ketones, leading to tertiary nitroaldols, is an elusive reaction so far limited to a reduced number of reactive substrates such as trifluoromethyl ketones or α-keto carbonyl compounds. Expanding the scop

Palladium-Catalysed Chemo- and Regioselective C–H Bond Acylation of Pyridine N-Oxides with Benzyl Halides and Alcohols

A palladium-catalysed method for the acylation of ortho C–H bonds of pyridine N-oxides using readily available benzyl halides and benzyl alcohols as the active acylating agents is described. This procedure provides a new approach to 2-acylpyridine N-oxides, which may be used as precursors for the synthesis of pharmaceuticals and agrochemicals.

Visible-Light-Induced Decarboxylative Acylation of Pyridine N-Oxides with α-Oxocarboxylic Acids Using Fluorescein Dimethylammonium as a Photocatalyst

Herein, the development of a visible-light-induced catalytic system to achieve the decarboxylative acylation of pyridine N-oxides with α-oxocarboxylic acids, at room temperature and using the organic dye fluorescein dimethylammonium as a new type of photocatalyst, is reported. A series of 2-arylacylpyridine N-oxides were selectively synthesized in moderate to good yields by controlling the polarity of the reaction solvent. The developed strategy was successfully applied in the synthesis of an important intermediate of the drug, acrivastine, on a gram scale. Notably, this is the first time that fluorescein dimethylammonium has been used to catalyze the Minisci-type C?H decarboxylative acylation reaction. The mechanism of decarboxylative acylation was studied by capturing adducts of acyl radicals and 1,1-diphenylethylene to confirm a radical mechanism. The disclosed catalytic system provides a green synthetic strategy for decarboxylative acylation without the use of additional oxidants or metal catalysts. (Figure presented.).

Rhodium-Catalyzed Pyridine N-Oxide Assisted Suzuki-Miyaura Coupling Reaction via C(O)-C Bond Activation

A rhodium-catalyzed Suzuki-Miyaura coupling reaction via C(O)-C bond activation to form 2-benzoylpyridine N-oxide derivatives is reported. Both the C(O)-C(sp2) and C(O)-C(sp3) bond could be activated during the reaction with yields up to 92%. The N-oxide moiety could be employed as a traceless directing group, leading to free pyridine ketones.

Visible-Light-Promoted Copper-Catalyzed Regioselective Benzylation of Pyridine N-Oxides versus Thermal Acylation Reaction with Toluene Derivatives

Copper-catalyzed visible light mediated direct C–H bond benzylation of pyridine N-oxides with toluene derivatives was accomplished by recent developments in photochemical carbon–carbon bond formation through a photo-induced bond-dissociation strategy. Thi

Iridium-Catalyzed Highly Enantioselective Transfer Hydrogenation of Aryl N-Heteroaryl Ketones with N-Oxide as a Removable ortho-Substituent

A highly enantioselective transfer hydrogenation of non-ortho-substituted aryl N-heteroaryl ketones, using readily available chiral diamine-derived iridium complex (S,S)-1f as a catalyst and sodium formate as a hydrogen source in a mixture of H2O/i-PrOH (v/v = 1:1) under ambient conditions, is described. The chiral aryl N-heteroaryl methanols were obtained with up to 98.2% ee by introducing an N-oxide as a removable ortho-substituent. In contrast, no more than 15.1% ee was observed in the absence of an N-oxide moiety. Furthermore, the practical utility of this protocol was also demonstrated by gram-scale asymmetric synthesis of bepotastine besilate in 51% total yield and 99.9% ee.

Copper-Catalyzed Aerobic Oxygenation of Benzylpyridine N-Oxides and Subsequent Post-Functionalization

A copper-catalyzed aerobic oxidation of benzylpyridine N-oxides is reported. The N-oxide moiety acts as a built-in activator for the benzylic methylene oxidation, without requirement of additives. Reaction conditions were identified which suppress undesired benzoylpyridine formation via N-deoxygenation involving intermolecular oxygen transfer. The versatility of the N-oxide group of the benzoylpyridine N-oxide reaction products for post-functionalization of the pyridine ring is demonstrated through efficient C–C, C–N, C–O and C–Cl bond forming procedures, with both nucleophiles and electrophiles. Finally, the applicability of the new synthetic methodology is demonstrated in an alternative route towards the antihistaminic drug Acrivastine via three consecutive N-oxide activated C–H functionalization processes, starting from picoline N-oxide. (Figure presented.).

Bifunctional Oxo-Tethered Ruthenium Complex Catalyzed Asymmetric Transfer Hydrogenation of Aryl N-Heteroaryl Ketones

A facile asymmetric transfer hydrogenation of ortho-substituted aryl N-heteroaryl ketones and non-ortho-substituted N-oxide of aryl N-heteroaryl ketones using a readily available oxo-tethered ruthenium complex as a catalyst and sodium formate as a hydrogen source in an aqueous solution has been discovered. A variety of chiral aryl N-heteroaryl methanols were obtained with up to 99.9% ee.

Silver catalyzed decarboxylative acylation of pyridine-N-oxides using α-oxocarboxylic acids

Silver catalyzed acylation of pyridine-N-oxides by α-oxocarboxylic acid is demonstrated. This decarboxylative acylation using a metal catalyst takes place at 50°C via a radical process.

Oxidation reactions using polymer-supported 2-benzenesulfonyl-3-(4- nitrophenyl)oxaziridine

A thermally stable polymer-supported oxidant has been developed. Polymer-supported 2-benzenesulfonyl-3-(4-nitrophenyl)oxaziridine was applied to microwave-assisted reactions that occurred at high temperatures and was shown to oxidize alkenes, silyl enol ethers, and pyridines to the corresponding epoxides and pyridine N-oxides in excellent to good yields and with much shorter reaction times. It also enabled tetrahydrobenzimidazoles to be oxidatively rearranged to spiro fused 5-imidazolones in a more efficient manner. Recycling of the polymer-supported oxidant is also possible with minimal loss of activity after several reoxidations.