5174-92-5

Basic information

• Product Name: 3-Phenyl-1,8-naphthyridin-2(1H)-one
• Synonyms: 3-Phenyl-1,8-naphthyridin-2(1H)-one
• CAS NO: 5174-92-5
• Molecular Formula: C₁₄H₁₀N₂O
• Molecular Weight: 222.242
• Mol File: 5174-92-5.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-Phenyl-1,8-naphthyridin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Phenyl-1,8-naphthyridin-2(1H)-one(5174-92-5)
• EPA Substance Registry System: 3-Phenyl-1,8-naphthyridin-2(1H)-one(5174-92-5)

Safety Data

• Hazardous Substances Data: 5174-92-5(Hazardous Substances Data)

Upstream product

• 5174-94-7 2-amino-3-phenyl-1,8-naphthyridine 
• 7521-41-7 2-Aminonicotinaldehyde 
• 140-29-4 phenylacetonitrile 
• 128071-75-0 2-bromopyridine-3-carboxaldehyde 
• 103-81-1 Benzeneacetamide 

Downstream Products

• 33760-73-5 2-chloro-3-phenyl-1,8-naphthyridine 
• 847613-60-9 ethyl (2-oxo-3-phenyl-2H-[1,8]naphthyridin-1-yl)-acetate 
• 928342-64-7 (2-oxo-3-phenyl-2H-[1,8]naphthyridin-1-yl)-acetic acid (1-phenyl-ethylidene)-hydrazide 
• 928342-65-8 (2-oxo-3-phenyl-2H-[1,8]naphthyridin-1-yl)-acetic acid (1-p-tolyl-ethylidene)-hydrazide 
• 928342-68-1 (2-oxo-3-phenyl-2H-[1,8]naphthyridin-1-yl)-acetic acid [1-(4-bromo-phenyl)-ethylidene]-hydrazide 
• 928342-67-0 (2-oxo-3-phenyl-2H-[1,8]naphthyridin-1-yl)-acetic acid [1-(4-chloro-phenyl)-ethylidene]-hydrazide 
• 928342-66-9 (2-oxo-3-phenyl-2H-[1,8]naphthyridin-1-yl)-acetic acid [1-(4-methoxy-phenyl)-ethylidene]-hydrazide 
• 928342-70-5 (2-oxo-3-phenyl-2H-[1,8]naphthyridin-1-yl)-acetic acid [1-(4-nitro-phenyl)-ethylidene]-hydrazide 
• 928342-69-2 (2-oxo-3-phenyl-2H-[1,8]naphthyridin-1-yl)-acetic acid [1-(3-nitro-phenyl)-ethylidene]-hydrazide 
• 928342-71-6 (2-oxo-3-phenyl-2H-[1,8]naphthyridin-1-yl)-acetic acid (1-naphthalen-2-yl-ethylidene)-hydrazide 
• 847613-61-0 (2-oxo-3-phenyl-2H-[1,8]naphthyridin-1-yl)acetic acid hydrazide 
• 847613-62-1 (2-oxo-3-phenyl-2H-[1,8]naphthyridin-1-yl)acetic acid benzylidene hydrazide 
• 847613-63-2 (2-oxo-3-phenyl-2H-[1,8]naphthyridin-1-yl)-acetic acid (4-methyl-benzylidene)-hydrazide 
• 847613-66-5 (2-Oxo-3-phenyl-2H-[1,8]naphthyridin-1-yl)-acetic acid [1-(4-chloro-phenyl)-meth-(E)-ylidene]-hydrazide 

Relevant articles and documents

A Simple “Green” Synthesis of Novel Bis(3-aryl-1,8-naphthyridin-2-yl)sulfanes and 2-(Methylthio)-3-aryl-1,8-naphthyridines under Microwave Irradiation and Conventional Conditions

An eco-friendly and highly efficient synthesis of substituted bis(3-aryl-1,8-naphthyridin-2-yl)-sulfanes and 2-(methylthio)-3-aryl-1,8-naphthyridines under microwave and conventional conditions. The products are obtained with high yields and purity within short reaction time. The synthesized derivatives are screened for anti-microbial activity against bacteria and fungi. Molecular docking of the synthesized compounds with DNA Gyrase is studied.

An Efficient Microwave-Assisted Synthesis of Novel 2-{4-[(3-Aryl-1,8-naphthyridin-2-yl)amino]phenyl}-1H-benzo[de]isoquinoline-1,3(2H)-diones and Their Antimicrobial Activity

The Buchwald–Hartwig amination reaction between 2-chloro-3-aryl-1,8-naphthyridines and 2-(4-aminophenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione in the presence of the catalytic system Pd(PPh3)4 and the base KO-t-Bu in toluene was studied. The reaction was initiated by microwave irradiation. Highly efficient synthesis has been developed for 2-{4-[(3-aryl-1,8-naphthyridin-2-yl)amino]phenyl}-1H-benzo[de]isoquinoline-1,3(2H)-diones. Structures of the synthesized compounds were evaluated by IR, 1H and 13C NMR spectroscopy. All products were tested for antimicrobial activity against Escheria coli, Bacillus subtilis, Klebsiella pneumoniae, and Staphylococcus aureus.

Synthesis of 1,2,4-triazolo[4,3-a] [1,8]naphthyridines

2-Hydroxy-3-phenyl-1,8-naphthyridine (2) on treatment with POCl3 gives 2-chloro-3-phenyl-1,8-naphthyridine (3) which on hydrazinolysis yields 2-hydrazino-3-phenyl-1,8-naphthyridine (4). The hydrazine 4 on condensation with aromatic aldehydes in ethanol containing a catalytic amount of gl. acetic acid affords 3-phenyl-1,8-naphthyridin-2-yl hydrazones (5), which on oxidative cyclization with nitrobenzene under reflux results in the formation of 1-aryl-4-phenyl-1,2,4-triazolo[4,3-a][1,8]naphthyridines (6). Further, 4 when treated with formic acid and gl. acetic acid yields the respective 1,2,4-triazolo[4,3-a][1,8]naphthyridines (7 and 8). The structures of the compounds 3-8 have been established on the basis of their elemental analyses and spectral (IR, 1H NMR and mass) data and are evaluated for their antimicrobial activities.