867267-26-3

Usage

Chemical structure

An aldehyde derivative of nicotinic acid with two methoxy groups attached to the 2 and 5 positions of the benzene ring

Usage

Commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals

Applications

Used as a flavoring agent in food products in the flavor and fragrance industry

Biological activities

Has been studied for its potential antioxidant and anti-inflammatory properties.

InChI:InChI=1/C8H9NO3/c1-11-7-3-6(5-10)8(12-2)9-4-7/h3-5H,1-2H3

Upstream product

• 2591-86-8 N-Formylpiperidine 
• 867267-24-1 2,5-dimethoxypyridine 
• 867267-31-0 5-hydroxy-2-methoxy-pyridine-3-carbaldehyde 
• 74-88-4 methyl iodide 
• 51834-97-0 6-methoxypyridine-3-ol 
• 867267-30-9 2-methoxy-5-(triisopropylsilanyloxy)-pyridine-3-carbaldehyde 
• 867267-29-6 2-methoxy-5-(triisopropylsilanyloxy)pyridine 

Relevant academic research and scientific papers

ANTIBACTERIAL COMPOUNDS AND USES THEREOF

The present invention relates to compounds of formula (I) including any stereochemically isomeric form thereof, or pharmaceutically acceptable salts thereof, for the treatment of tuberculosis.

Solvent-dependent oxidations of 5- and 6-azaindoles to trioxopyrrolopyridines and functionalised azaindoles

A regioselective synthesis of 4,7-dimethoxy 5- and 6-azaindoles 2 has been achieved, based on the appropriate choice of ortho-directing or ortho-repulsing groups in the formylation of a pyridine ring. Studies on the regioselectivity of the formylation step and on the preparation of azidoacrylate intermediates 4 are described in this paper. The reactivity of the 5- and 6-azaindole structures towards BBr3-mediated selective monodemethylation and oxidative demethylation reactions were also investigated. The regioselectivity of the deprotection was confirmed using a chemical approach. Oxidation reactions were then carried out on either dimethoxy- or hydroxymethoxyazaindoles, in different solvents, using [bis(trifluoroacetoxy)iodo]benzene. In acetonitrile-water, trioxopyrrolopyridines 12 were obtained, whereas the formation of functionalised azaindoles 17 was observed in acetonitrile-methanol. The tautomeric structure of the trioxopyrrolopyridines was proved by X-ray diffraction analysis. The Royal Society of Chemistry.

A regioselective route to 5- and 6-azaindoles

The synthesis of 4,7-dimethoxy 5- and 6-azaindoles, a structural unit that is present in recently developed anti-HIV-1 agents, was achieved in a regioselective manner. The developed strategy is based on the appropriate choice of a protecting group during a lithium-mediated formylation step, followed by thermal cyclization of azidoacrylates. Georg Thieme Verlag Stuttgart.