360774-14-7

Usage

Uses

Used in Medicinal Chemistry:
2-(Benzyloxy)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile is used as a building block or intermediate in the synthesis of pharmaceuticals for its potential biological activity. It is particularly valuable in drug development due to its ability to target specific biological pathways or receptors.
Used in Drug Development:
In the pharmaceutical industry, 2-(Benzyloxy)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile is utilized as a key component in the creation of new drugs. Its unique structure allows it to interact with biological targets, potentially leading to the development of novel therapeutic agents.
Further research and studies are necessary to fully understand the properties and potential applications of 2-(Benzyloxy)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile, ensuring its safe and effective use in medicinal chemistry and drug development.

Upstream product

• 100-39-0 benzyl bromide 
• 108106-97-4 2-oxo-2,5,6,7-tetrahydro-3-cyano-1H-cyclopenta[b]pyridine-3-carbonitrile 
• 100-44-7 benzyl chloride 
• 120-92-3 cyclopentanone 

Downstream Products

• 234752-98-8 2-(Benzyloxy)-3-(3-[6-(benzyloxy)pyridin-2-yl]-1-{[tert-butyl(dimethyl)silyl]oxy}prop-2-ynyl)-6,7-dihydro-5H-cyclopenta[b]pyridine 
• 201274-51-3 1-[2-(Benzyloxy)-6,7-dihydro-5H-cyclopenta[b]pyridin-3-yl]-3-[6-(benzyloxy)pyridin-2-yl]prop-2-yn-1-ol 
• 201274-49-9 2-(Benzyloxy)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carbaldehyde 

Relevant academic research and scientific papers

Zinc (II)-mediated selective O-benzylation of 2-Oxo-1,2-dihydropyridines systems

The selective O-benzylation of 2-oxo-1,2-dihydropyridines plays a critical role in organic synthesis of natural products and biological active molecules. Herein we report a novel ternary system of ZnO, ZnCl2 and N,N-diisopropylethylamine (DIEA), that is highly effective for selective O-benzylation of 2-oxo-1,2-dihydropyridines using abundant substituted benzyl halides and related substituted 2-oxo-1,2-dihydropyridines compounds. This process allows access to a variety of O-benzyl products under mild reaction conditions, which are important synthetic intermediates in the protection of functional groups, and represents a new method toward the development for the O-benzylation of 2-oxo-1,2-dihydropyridines.

Fusicoccin synthesis by intramolecular [4+4] photocycloaddition of 2-pyridones: Stereocontrol of the cycloaddition and elaboration of the pentacyclic product

Intramolecular photocycloaddition of a three-carbon tethered pyrindinone-pyridone system yields the 5-8-5 ring system of the fusicoccin/ophiobolin/ceroplastol families. The stereoselectivity of the cycloaddition was found to be dependent on nitrogen substitution; N-methylation led to exclusively trans products while an absence of nitrogen substitution resulted in solvent-dependent stereoselectivity. Solvent and concentration effects for this cycloaddition were consistent with a hydrogen-bonded dimer that enforces a pro-cis conformation in nonpolar solvents and at higher concentrations. The cis-isomer, a fusicoccin synthesis intermediate, underwent a Cope rearrangement at ambient temperature but could be trapped efficiently as the mono epoxide, yielding a product with six new stereogenic centers. A four-step transformation of an amide carbonyl to a methyl group was achieved using a carbamoyl group to activate the amide for cleavage.

Fusicoccin ring system by [4 + 4] cycloaddition. 2. A model study

A synthetic approach to fusicoccin A utilizing intramolecular photocycloaddition of tethered 2-pyridones has been completed. This study has led to the first solvent-dependent 2-pyridone photocycloaddition yielding either cis or trans products. Epoxidation of the cis photoproduct is selective for the disubstituted alkene, stabilizes the product, and is properly located for installation of the trans-1,2-diol. Activation of the secondary amide by reaction with an isocyanate led to the reduction of the neopentyl amide carbonyl to a methyl group.