65182-60-7

Usage

Chemical structure

A naphthyridine core with a 4-chlorophenyl group attached at the 2-position.

Usage

Synthesis of pharmaceuticals and agrochemicals
Building block in the development of new drugs and pesticides

Applications

Medicinal chemistry
Treatment of various diseases

Research and development

Creation of new compounds with enhanced properties and activities

Importance

Valuable building block in drug discovery and development
Versatile and significant chemical in the field of pharmaceuticals and agrochemicals

Upstream product

• 7521-41-7 2-Aminonicotinaldehyde 
• 17059-59-5 1-(4-chloro-phenyl)-3-phenyl-propane-1,3-dione 
• 99-91-2 para-chloroacetophenone 
• 3391-10-4 1-(p-chlorophenyl)ethyl alcohol 
• 23612-57-9 (2-amino-3-pyridinyl)methanol 
• 102000-72-6 3-vinylpyridin-2-amine 

Relevant academic research and scientific papers

Transition metal-free α-methylation of 1,8-naphthyridine derivatives using DMSO as methylation reagent

A practical approach to the direct α-methylation of 1,8-naphthyridines under mild reaction conditions has been developed using simple and readily available DMSO as a convenient and environmentally friendly carbon source. This method is transition metal-free and highly chemoselective, shows good functional group tolerance, and uses DMSO as a methyl source, providing efficient and rapid access to an important compound class, 2-methyl-1,8-naphthyridines.

Sustainable synthesis of N-heterocycles in water using alcohols following the double dehydrogenation strategy

The present study describes the first example of synthesis of pharmaceutically relevant N-heterocycles like substituted quinolines, acridines and 1,8-naphthyridines in water under air using alcohols in presence of a new water soluble Ir-complex. The viability and efficiency of this approach was demonstrated by the efficient synthesis of biologically active natural product (±)-galipinine and gram scale synthesis of various N-heteroaromatics. Several kinetic experiments and DFT calculations were carried out to support the plausible reaction mechanism which disclosed that this system followed a concerted outer sphere mechanism for the dehydrogenation of alcohols.

Direct Access to Nitrogen Bi-heteroarenes via Iridium-Catalyzed Hydrogen-Evolution Cross-Coupling Reaction

Through cooperative actions of iridium catalyst and NaOTf additive we report a new direct access to nitrogen bi-heteroarenes via hydrogen-evolution cross-coupling of the β-site of indoles/pyrrole with the α-site of N-heteroarenes. The reaction proceeds in an atom- and redox-economic fashion together with the merits of an easily available catalyst system, broad substrate scope, excellent functional tolerance, and no need for external oxidants, offering a practical way to create π-conjugated systems.

Hydrogen-Transfer-Mediated α-Functionalization of 1,8-Naphthyridines by a Strategy Overcoming the Over-Hydrogenation Barrier

A general catalytic hydrogen transfer-mediated α-functionalization of 1,8-naphthyridines is reported for the first time that benefits from a hydrogen transfer-mediated activation mode for non-activated pyridyl cores. The pyridyl α-site selectively couples with the C8-site of various tetrahydroquinolines (THQs) to afford novel α-functionalized tetrahydro 1,8-naphthyridines, a class of synthetically useful building blocks and potential candidates for the discovery of therapeutic and bio-active products. The utilization of THQs as inactive hydrogen donors (HDs) appears to be a key strategy to overcome the over-hydrogenation barrier and address the chemoselectivity issue. The developed chemistry features operational simplicity, readily available catalyst and good functional group tolerance, and offers a significant basis for further development of new protocols to directly transform or functionalize inert N-heterocycles.

Microwave assisted synthesis of 1,8- naphthyridines

A highly efficient and practical methodology for the synthesis of 2-aryl-1.8-naphthyridines 3 is described starting from 2-aminonicotinaldehyde 1 and various acetophenones under microwave conditions.

Substituted 1,8-Naphthyridines: Part VI - Synthesis of 3-Aroyl-2-phenyl-1,8-naphthyridines

The condensation of 2-aminonicotinaldehyde (1) with ω-benzoylacetophenones (2) leads to either 3-aroyl-2-phenyl-1,8-naphthyridines (3) in the presence of gl. acetic acid containing a catalytic amount of conc.H2SO4, or to 2-aryl-1,8-naphthyridines (4) in e