51420-71-4

Usage

InChI:InChI=1/C10H10N2O/c1-6-5-7(2)11-10-8(6)3-4-9(13)12-10/h3-5H,1-2H3,(H,11,12,13)

Upstream product

• 39565-07-6 7-amino-2,4-dimethyl-1,8-naphthyridine 
• 141-86-6 2.6-diaminopyridine 
• 123-54-6 acetylacetone 

Downstream Products

• 77223-21-3 7-chloro-2,4-dimethyl-1,8-naphthyridine 
• 7544-64-1 2,4-dimethyl[1,8]naphthyridine 
• 65541-95-9 5,7-dimethyl-1,2,3,4-tetrahydro[1,8]naphthyridine 
• 79060-65-4 4-<(2-oxo-2-phenyl)ethyl>-7-hydroxy-2-methyl-1,8-naphthyridine 
• 79060-68-7 2-<(2-oxo-2-phenyl)ethyl>-7-hydroxy-4-methyl-1,8-naphthyridine 

Relevant academic research and scientific papers

2-Amino-5,7-dimethyl-1,8-naphthyridine as a fluorescent reagent for the determination of nitrite

A new fluorescent reagent 2-amino-5,7-dimethyl-1,8-naphthyridine (ADMND) was proposed for the determination of trace nitrite. The reaction is based on the diazotization of naphthyridine amine with nitrite to form a diazonium salt that hydrolyzed when boiling to give hydroxyl group substituted naphthyridine. Fluorescence quenching degree of ADMND by nitrite ion is linear in the nitrite concentration range of 1 × 10-7 to 2.5 × 10-6 mol l-1 with a detection limit of 4.06 × 10-8 mol l-1. Reaction and determination acidity for nitrite is the same which made the method much simpler compared with the widely accepted fluorescence method with DAN as a fluorescence reagent.

A flexible synthesis of naphthyridine derivatives through diazotization, triflation, and Suzuki reaction

A facile and suitable method for the synthesis of different 1,8-Naphthyridine derivatives is depicted. The procedure is based on the diazotization and triflation reactions of commercially available 1,8-naphthyridine-2-amines followed by cross-coupling with aromatic and heteroaromatic boronic acids through Suzuki reaction. These processes reserved the required yields in high percentage. All synthesized compounds were identified by spectral data.

The First 1-Hydroxypropylidenebisphosphonic Acid with 1,8-Naphthyridinone Substituent: Synthesis and Structure

1-Hydroxy-3-(5,7-dimethyl-2-oxo-1,2-dihydro-1,8-naphthyridin-1-yl)propylidenebisphosphonic acid has been synthesized. The structure of the acid and its precursors synthesized for the first time, 3-(5,7-dimethyl-2-oxo-1,2-dihydro-1,8-naphthyridin-1-yl)propionic acid and the corresponding methyl ester, in the solid state and in the DMSO solution has been elucidated by means of vibrational (IR and Raman) and multinuclear (1H, 13C, and 31P) NMR spectroscopy.

Cu(I) and Pb(II) complexes containing new tris(7-naphthyridyl)methane derivatives: Synthesis, structures, spectroscopy and geometric conversion

Two novel facial-capping tris-naphthyridyl compounds, 2-chloro-5-methyl-7- ((2,4-dimethyl-1,8-naphthyridin-7(1H)-ylidene)(2,4-dimethyl-1, 8-naphthyridin-7-yl))methyl-1,8-naphthyridine (L1) and 2-chloro-7-((2-methyl-1,8-naphthyridin-7(1H)-ylidene)(2-methyl-1, 8-naphthyridin-7-yl))methyl-1,8-naphthyridine (L2), as well as their Cu(I) and Pb(II) complexes, [CuLa(PPh3)]BF4 (1) (PPh3 = triphenylphosphine, La = bis(2,4-dimethyl-1,8- naphthyridin-7-yl)(2-chloro-5-methyl-1,8-naphthyridin-7-yl)methane), [CuL b(PPh3)]BF4 (2) (Lb = bis(2-methyl-1,8-naphthyridin-7-yl)(2-chloro-1,8-naphthyridin-7-yl)methane), [Pb(OLa)(NO3)2] (3) (OLa = bis(2,4-dimethyl-1,8-naphthyridin-7-yl)(2-chloro-5-methyl-1,8-naphthyridin-7-yl) methanol) and [Pb(Lb)2][Pb(CH3OH)(NO 3)4] (4), have been synthesized and characterized by X-ray diffraction analysis, MS, NMR and elemental analysis. The structural investigations revealed that the transfer of the H-atom at the central carbon to an adjacent naphthyridine-N atom affords L1 and L2 possessing large conjugated architectures, and the central carbon atoms adopt the sp2 hybridized bonding mode. The reversible hydrogen transfer and a geometric configuration conversion from sp2 to sp3 of the central carbon atom were observed when Pb(II) and Cu(I) were coordinated to L1 or L2. The molecular energy changes accompanying the hydrogen migration and titration of H+ to different receptor-N at L1 were calculated by density functional theory (DFT) at the SCRF-B3LYP/6-311++G(d,p) level in a CH2Cl2 solution, and the observed lowest-energy absorption and emission for L1 and L 2 can be tentatively assigned to an intramolecular charge transfer (ICT) transition in nature.

Pyridine and related aza heterocycle derivatives as cardiovascular agents

Novel pharmaceutical compounds and compositions having nitrogen containing ring systems which may be represented by the following structural formula: wherein R1 or R3 is a moiety of the formula: wherein R6 is selected from either hydrogen or acetyl; R7 is selected from 2, 3 or 4-pyridyl or 1-imidazolyl and Q is -(CH2)n, where n is an integer from 1 to 5 and R1 and R2, R2 and R3, R3 and R4 or R4 and R5 taken together may be -CH=CH-CH=CH-. The compounds and compositions are useful as inhibitors of thromboxane synthetase and in the treatment of hypertension and arrythmia in mammals.

REGIOINTEGRITY OF CARBANIONS DERIVED BY SELECTIVE METALATIONS OF DIMETHYLPYRIDINES AND -QUINOLINES

Metalation of 2,4-dimethylpyridine and -quinolines by strong basic reagents in ethyl ether in the absence of HMPA affords 2-lithiomethyl derivatives regardless of the reaction length.The use of THF in such metalations promotes the formation of the 2-lithiomethyl reagents which isomerize to the more thermodynamically stable 4-lithiomethyl derivatives after relatively long reaction periods or in the presence of amines or an excess of the parent heterocycle.The latter derivatives appear to be formed directly from the heterocycles in ammonia or in the presence of HMPA.The results are discussed in terms of "coordination-only" versus "acid-base" limiting mechanisms for metalations as a function of ion pairing.NMR spectra for certain of the carbanions in ethyl ether and THF are described which support the above concepts.Related metalations of 2,4-dimethylquinoline-N-oxide give only the 2-lithiomethyl derivative.Similar reactions of 7-hydroxy-2,4-dimethyl-1,8-naphthyridine lead in synthetically useful yields to derivatization of the 2- and 4-methyl groups via dianions by using n-butyllithium in ethyl ether and sodium amide in liquid ammonia, respectively, followed by the addition of appropriate electrophiles.