2683-66-1

Usage

Chemical Properties

White to off-white crystalline powder

Uses

4-Benzyloxypyridine N-Oxide is an intermediate in the synthesis of 4-Hydroxy-1-methyl-2-pyridone (H947715), a reactant used in the synthesis of 3-deaza-3-halouracil nucleosides with cytostatic activity in three cancer cell lines.

General Description

4-(Benzyloxy)pyridine N-oxide is a 4-substituted pyridine-1-oxide. It undergoes hydrogenation over palladium to afford pyridine. It participates in the stereoselective synthesis of substituted pyridines, piperidines and piperazines.

InChI:InChI=1/C12H11NO2/c14-13-8-6-12(7-9-13)15-10-11-4-2-1-3-5-11/h1-9H,10H2

Upstream product

• 93-59-4 Perbenzoic acid 
• 49826-70-2 4-(benzyloxy)pyridine 
• 137858-02-7 4-(N-pyridinium)pyridine-N-oxide chloride tetracyanoethylene complex 
• 100-51-6 benzyl alcohol 
• 1124-33-0 4-nitraminopyridine N-oxide 
• 5421-92-1 1-(4-pyridyl)pyridinium chloride hydrochloride 
• 1121-76-2 4-chloropyridine N-oxide 
• 694-59-7 pyridine N-oxide 

Downstream Products

• 626-64-2 pyridin-4-ol 
• 49826-70-2 4-(benzyloxy)pyridine 
• 107624-22-6 4-(benzyloxy)-2-methylpyridine 
• 935266-97-0 4-(benzyloxy)-2-phenyl-pyridine-1-oxide 
• 1060724-82-4 7-benzyloxytetrazolo[1,5-a]pyridine 
• 100382-00-1 4-benzyloxypyridine-2-carbonitrile 
• 1092694-31-9 4-benzyloxy-2-deuteriumpyridine 1-oxide 
• 1092694-33-1 4-benzyloxy-2-iodopyridine 1-oxide 
• 1092694-61-5 4-benzyloxy-2-(cyclohexyl-1-ol)pyridine 1-oxide 
• 1092694-32-0 4-benzyloxy-2-(phenylmethanol)pyridine 1-oxide 
• 1620125-59-8 4-(benzyloxy)-2-(5-methylthiophen-2-yl)pyridine 1-oxide 
• 1620125-60-1 4-(benzyloxy)-2-(5-ethylfuran-2-yl)pyridine 1-oxide 

Relevant academic research and scientific papers

FUMAGILLOL COMPOUNDS AND METHODS OF MAKING AND USING SAME

Disclosed herein, in part, are fumagillol compounds and methods of use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making fumagillol compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.

Visible Light-Mediated Decarboxylative Alkylation of Pharmaceutically Relevant Heterocycles

A net redox-neutral method for the decarboxylative alkylation of heteroarenes using photoredox catalysis is reported. Additionally, this method features the use of simple, commercially available carboxylic acid derivatives as alkylating agents, enabling the facile alkylation of a variety of biologically relevant heterocyclic scaffolds under mild conditions.

Nickel-catalyzed C–H trifluoromethylation of pyridine N-oxides with Togni's reagent

The first nickel-catalyzed C–H trifluoromethylation of pyridine N-oxides with Togni's reagent has been achieved. Trifluoromethylation proceeds smoothly under mild conditions with moderate functional group compatibility. Notable advantages of this method include the using of low cost of nickel catalyst, and its simple convenient operation.

Visible-Light-Induced C2 Alkylation of Pyridine N-Oxides

A photoredox catalytic method has been developed for the direct C2 alkylation of pyridine N-oxides. This reaction is compatible with a range of synthetically relevant functional groups for providing efficient synthesis of a variety of C2-alkylated pyridine N-oxides under mild conditions. Mechanistic studies are consistent with the generation of a radical intermediate along the reaction pathway.

Base free regioselective synthesis of α-triazolylazine derivatives

A regioselective α-heteroarylation followed by deoxygenation towards the synthesis of variety of azine triazole from simple azine N-oxides derivatives and N-tosyl-1,2,3-triazoles has been described. The reaction is metal free and base free with shorter reaction time, high yields and a broad substrate scope.

Rational design and synthesis of 4-substituted 2-pyridin-2-ylamides with inhibitory effects on SH2 domain-containing inositol 5′-phosphatase 2 (SHIP2)

Novel 4-substituted 2-pyridin-2-ylamides were developed using in-silico ligand-based drug design (LBDD) in an attempt to identify inhibitors of SH2-containing 5′-inositol phosphatase 2 (SHIP2), which is implicated in insulin-resistant type 2 diabetes. Among the compounds synthesized, N-[4-(4-chlorobenzyloxy)pyridin-2-yl]-2-(2,6-difluorophenyl)- acetamide (CPDA, 4a) was identified as a potent SHIP2 inhibitor. CPDA was found to enhance in vitro insulin signaling through the Akt pathway more efficiently than the previously reported SHIP2 inhibitor AS1949490, and ameliorated abnormal glucose metabolism in diabetic (db/db) mice.

Discovery of N-substituted pyridinones as potent and selective inhibitors of p38 kinase

The identification and evolution of a series of potent and selective p38 inhibitors is described. p38 inhibitors based on a N-benzyl pyridinone high-throughput screening hit were prepared and their SAR explored. Their design was guided by ligand bound co-

The first total synthesis of novel human chymase inhibitor SPF32629A

The first total synthesis of SPF32629A, a novel human chymase inhibitor, has been accomplished from the readily available precursor 4-nitropyridine N-oxide, following an efficient strategy with a sequence of eight straightforward steps.

PYRIDONE DERIVATIVE

The invention provides pyridone derivatives represented by a general formula (I) [in the formula, R 1 and R 2 may be same or different and stands for H, etc., or R 1 and R 2 may form an aliphatic nitrogen-containing heterocyclic group together with the N to which they bind; X 1 -X 3 may be same or different and stand for methine or N, provided not all of them simultaneously stand for nitrogen; X 4 -X 7 may be same or different and stand for methine or N, provided that three or more of them do not simultaneously stand for N; Y 1 and Y 3 may be same or different and stand for single bond, -0-, -NR-, -S-, etc ; Y 2 stands for lower lkylene, etc.; R stands for H, etc., L stands for methylene; Z 1 and Z 2 may be same or different and stand for single bond or lower alkylene; or R 1 , L and Z 2 may form an aliphatic nitrogen-containing heterocyclic group with the N to which R 1 binds; and Ar stands for aromatic carbocyclic group, etc.].

THE MOLECULAR COMPLEX OF 4-(N-PYRIDINIUM)PYRIDINE-N-OXIDE CHLORIDE WITH TETRACYANOETHYLENE IN THE SYNTHESIS OF SUBSTITUTED PYRIDINE N-OXIDES

The structure of the complex of 4-(N-pyridinium)pyridine-N-oxide chloride with tetracyanoethylene was studied by 13C NMR spectroscopy.The results of the investigation, suggesting the use of this complex in the synthesis of substituted pyridine derivatives, were confirmed experimentally by its reaction with oxygen and with nitrogen-containing nucleophiles.