56664-26-7

Usage

InChI:InChI=1/C13H13N/c1-11-6-5-9-14-13(11)10-12-7-3-2-4-8-12/h2-9H,10H2,1H3

Upstream product

• 82198-73-0 2-benzyl-3-methylpyridine N-oxide 
• 108-86-1 bromobenzene 
• 1251919-69-3 potassium 2-(3-methylpyridin-2-yl)acetate 
• 1003-73-2 3-picoline-N-oxide 
• 103-54-8 cinnamyl acetate 
• 3430-17-9 2-bromo-3-picoline 
• 6921-34-2 benzylmagnesium chloride 
• 100-52-7 benzaldehyde 
• 16214-99-6 N-benzyl-3-methyl-pyridinium chloride 
• 108-99-6 3-Methylpyridine 
• 100-39-0 benzyl bromide 

Downstream Products

• 82198-73-0 2-benzyl-3-methylpyridine N-oxide 

Relevant academic research and scientific papers

Acylation of 2-benzylpyridine N-oxides and subsequent in situ [3,3]-sigamatropic rearrangement reaction

An effective method for the acylation of 2-benzylpyridine N-oxides and their fast in situ [3,3]-sigmatropic rearrangement was reported. This transformation has a wide substrate scope under mild conditions, giving moderate to excellent yields. The application for the synthesis of chiral phenyl-2-pyridylmethanol products was briefly explored. Furthermore, an interesting example of tandem substitution and in situ [3,3]-sigamatropic rearrangement of 2-benzylpyridine N-oxide with benzenecarboximidoyl chloride was reported.

Photocatalyzed ortho-Alkylation of Pyridine N-Oxides through Alkene Cleavage

A photocatalyzed reaction of pyridine N-oxides with alkenes gives ortho-alkylated pyridines with cleavage of the carbon–carbon double bond. Benzyl and secondary alkyl groups are incorporated at the ortho position of pyridines in one pot.

A VERSATILE LIGAND FOR PALLADIUM-CATALYZED META-C-H FUNCTIONALIZATIONS

A class of mono-protected 3-amino-2- hydroxypyridine (MPAHP) ligands that enable the meta- C-H arylation of anilines, phenols, phenylacetic acids, and biologically relevant heterocyclic compounds using norbornene as a transient mediator is disclosed. The applicability of this meta-arylation methodology in the pharmaceutical industry is illustrated for heteroaryl substrates and heteroaryl iodide coupling partners, a feat made possible by using the MPAHP ligand. The enabling nature of MPAHP ligands to achieve other meta-C-H functionalization processes is also illustrated by the development of a meta-C-H amination reaction and a meta-C-H alkynylation reaction.

Ligand-Promoted Meta-C-H Arylation of Anilines, Phenols, and Heterocycles

Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic aryl iodides as coupling partners is also realized for the first time using this ligand. The utility for this transformation for drug discovery is showcased by allowing the meta-C-H arylation of a lenalidomide derivative. The first steps toward a silver-free protocol for this reaction are also demonstrated.

Palladium-catalyzed decarboxylative couplings of 2-(2-Azaaryl)acetates with aryl halides and triflates

Pd-catalyzed decarboxylative cross-couplings of 2-(2-azaaryl)acetates with aryl halides and triflates have been discovered. This reaction is potentially useful for the synthesis of some functionalized pyridines, quinolines, pyrazines, benzoxazoles, and benzothiazoles. Theoretical analysis shows that the nitrogen atom at the 2-position of the heteroaromatics directly coordinates to Pd(II) in the decarboxylation transition state.

Proton-Transfer Processes in Well-Defined Media: Experimental Investigation of Photoinduced and Thermal Proton-Transfer Processes in Single Crystals of 2-(2,4-Dinitrobenzyl)pyridine Derivatives

A detailed spectroscopic study of photoinduced and thermally activated proton-transfer processes for a series of different crystals of 2-(2,4-dinitrobenzyl)pyridine derivatives has been performed.The quantitative analysis of ground- and excited-state activation barriers and preexponential factors in deuterated and nondeuterated crystals shows clearly that the observed photochromism is linked to a proton-transfer process.Furthermore, it is clearly seen that the supramolecular environment of the transferred proton participates in the proton-transfer process.These supramolecular effects control the relative rates and efficiencies of the observed proton-transfer processes in both the ground and excited state, yielding, at room temperature, photoproducts having lifetimes ranging between hours and weeks.At least two proton-accepting groups may be active in the abstraction of the proton from its relatively stable benzylic position.Additionally, low-temperature measurements of proton-transfer processes show that tunneling processes prevail at temperatures below 100 K only in the excited state.No evidence for tunneling could be found for ground-state processes.

Flash Vacuum Pyrolysis of Substituted Pyridine N-Oxides and Its Application to Syntheses of Heterocyclic Compounds

Flash vacuum pyrolysis of 2-picoline N-oxide gave 2-picoline, pyridine, 2-ethylpyridine, 2-vinylpyridine, 2-pyridylmethanol, bis(2-pyridyl)methane, 1,2-bis(2-pyridyl)ethane, and 1,2-bis(2-pyridyl)ethylene.These reactions are explained by intermediary participation of the 2-picolyl radical.Flash vacuum pyrolysis of methyl-substituted 2-benzylpyridine N-oxides led to methyl-substituted pyridoindoles or to benzoquinoline in moderate yields.