Tag: M.W:100-200

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of 1,8-naphthyridine homologs and their hydrogenation》. Authors are Ochiai, Eiji; Miyaki, Komei.The article about the compound:4-Methyl-1,8-naphthyridinecas:1569-17-1,SMILESS:CC1=C2C=CC=NC2=NC=C1).HPLC of Formula: 1569-17-1. Through the article, more information about this compound (cas:1569-17-1) is conveyed.

In earlier work (CA 33:2525.5) it was found that Me 1,4-dihydroxy-2,5-naphthyridine-3-carboxylate (C. A. numbering, 5,8-dihydroxy-1,6-naphthyridine-7-carboxylate) and the 1-Cl compound on catalytic hydrogenation take up H only on the nonsubstituted pyridine ring. In continuation of this work, 2,4-dimethyl- (I) and 4-methyl-1,8-naphthyridine (II) have been synthesized and a similar phenomenon on hydrogenation has been observed. In the meantime some other 1,8-naphthyridines described in this paper have been prepared by analogous methods by Mangini (preceding abstract). 7-Amino derivative of I (0.5 g. from 2 g. 2,6-diaminopyridine, 2 g. CH2Ac2 and 1 g. fused ZnCl2 heated 3 hrs. at 120-30°), m. 220° (Ac derivative, pale yellow, m. 300°), converted by diazotization in 40% H2SO4 into the 7-HO compound, m. 251°, which, heated 30 min. in a sealed tube at 140° with POCl3, gives the 7-Cl compound, m. 146-7°; this, boiled 30 min. with 20% MeONa in MeOH, gives the 7-MeO compound, m. 65° (picrate, m. 188-9°). Hydrogenation of 1 g. of the HO compound in 20 g. alc. with 1 g. Ni-kieselguhr under 110 atm. of H for 10 hrs. at 170-80° gave, along with 0.6 g. unchanged material, 0.2 g. of a dihydro derivative, C10H12N2O, m. 175-80°. The Cl compound (0.5 g.), shaken in 10% KOH-MeOH with 0.2 g. of 20% Pd-charcoal and H until about 1.2 mols. H had been absorbed, and the product chromatographed in benzene through Al2O3, yielded about 0.05 g. I, m. 85-6° (HCl salt, decomposes 240°; picrate, decomposes 204-6°; methiodide, yellow needles with 1 H2O, m. 93-4; chloroplatinate, I.H2PtCl6, decomposes 242-4°; chloroaurate, decomposes 166-7°). When 0.1 g. of the Cl compound in 10 cc. of 10% KOH-MeOH was hydrogenated to saturation with 0.5 g. of 20% Pd-charcoal it yielded the tetrahydro derivative (III) of I described below. With 1.2 g. of the Cl compound in 20 cc. of 5% KOH-MeOH, 0.5 g. PdO-CaCO3 and a trace of Pd-charcoal, the hydrogenation stopped in 30 min. (about 170 cc. H absorbed) and 0.8 g. I was obtained. Shaken in 10 cc. AcOH with 0.1 g. Pt oxide and H to saturation, 0.5 g. I absorbed about 160 cc. H and yielded 0.5 g. of a tetrahydro derivative (III), m. 118°, giving a pos. Liebermann reaction (picrate, m. 207°; Ac derivative, m. 42-3°); III was also obtained in 0.85-g. yield from 1 g. I in 50 cc. cyclohexane and 5 cc. alc. with 1 g. Raney Ni heated under an initial H pressure of 70 atm. 2 hrs. at 120° and 2 hrs. at 190°. III was unchanged by 4 hrs. treatment in AcOH with Pt oxide and 110 atm. H pressure, at room temperature With Na in boiling alc., however, it yielded the decahydro derivative of I, easily subliming needles, m. 92-3° (di-Ac derivative, thick oil, b0.02 135-45°). 2,7-Dichloro-4-methyl-1,8-naphthyridine in 10% KOH-MeOH hydrogenated with PdO-CaCO3 and a trace of Pd-charcoal gave, together with a mono-Cl compound, C9H7ClN2, m. 104°, chiefly (about 70%) II, b0.05 147-8° (picrate, decomposes 204-5°; perchlorate, m. 180-1°). II (1 g.) in 10 cc. AcOH with 0.5 g. Pt oxide and H yielded a mixture of 2 isomeric tetrahydro derivatives, separated by fractional crystallization from petr. ether: 0.2 g. of a more soluble isomer A (IV), m. 62-3°, giving a pos. Liebermann reaction (Bz derivative, m. 86-7°), and about 0.8 g. of a less soluble isomer B (V), m. 102-3° (picrate, decomposes 248°; Bz derivative, m. 105-6°; nitro derivative, m. 217-18° and giving a pos. Liebermann reaction, prepared by treating the tetrahydride in cold H2SO4 (dry ice-acetone) with fuming HNO3 (d.1.6), pouring on ice, crystallizing from alc., heating the crystals (m. 124-5°) in concentrated H2SO4 at 60°, again pouring on ice, filtering, making alk. with Na2HPO4 and extracting with ether). V is unchanged by hydrogenation in AcOH with PtO and 65 atm. H pressure. With Na in boiling AmOH, both isomers yield the same (racemic) decahydro derivative of II, b0.1 70-80°, m. 87°, gives a pos. Liebermann reaction (picrate, decomposes 210°). The structures of III, IV and V have not been definitely established but the following considerations make it highly probable what they are. The work of earlier investigators on the hydrogenation of quinoline homologs with Ni and H under pressure and with Sn and HCl has shown that Me groups have a disturbing influence on the hydrogenation of the ring half on which they are substituted whereas Na and alc. readily hydrogenate the Me-substituted rings. This disturbing effect of Me groups is ascribed to the inductive effect of the Me group. III is considered to be the 5,6,7,8-tetrahydro compound To further confirm this, III was heated in a little alc. with an excess of ClCH2COMe for 4 hrs. at 100°; the resulting addition product, C15H21ClN22O2, m. 181-2°, allowed to stand 1 day in a little water with 2 drops of 10% Na3CO3, gave, in addition to unchanged III, a resin whose blue Ehrlich reaction pointed to the presence of an indolizine ring. Such a ring can be formed only from a nonhydrogenated 2-methylpyridine. IV is considered to be the 1,2,3,4- and V the 5,6,7,8-tetrahydro compound because the latter is formed in the larger amount; its higher m. p. is also in harmony with such an assumption.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 16710-11-5, is researched, SMILESS is CSC1=NC(O)=NC(C)=C1, Molecular C6H8N2OSJournal, Russian Journal of General Chemistry called 4-arylamino-2-(2-acetoxyethyl)amino-6-methylpyrimidines: Synthesis, deacetylation, and biological activity, Author is Erkin, A. V.; Krutikov, V. I., the main research direction is ethanolamine acetate arylaminopyrimidinyl tuberculostatic preparation; pyrimidinediamine acetoxyethyl aryl tuberculostatic preparation; deacetylation acetoxyethylaminopyrimidine.Application In Synthesis of 4-Methyl-6-(methylthio)pyrimidin-2-ol.

The reaction of 2-(2-acetoxyethyl)amino-4-chloro-6-methylpyrimidine with aromatic amines leads to a series of 4-arylamino-2-(2-acetoxyethyl)amino-6-methylpyrimidines. Deacetylation of these compounds proceeds in both acidic and basic media. Most of the (arylamino)pyrimidines obtained exhibit a pronounced antituberculous effect.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Naphthyridine chemistry. V. One-step synthesis of 1,8-naphthyridines》. Authors are Paudler, William W.; Kress, Thomas J..The article about the compound:4-Methyl-1,8-naphthyridinecas:1569-17-1,SMILESS:CC1=C2C=CC=NC2=NC=C1).Safety of 4-Methyl-1,8-naphthyridine. Through the article, more information about this compound (cas:1569-17-1) is conveyed.

cf. CA 66, 6881q; 65, 16955a; 64, 5057c. 2-Aminopyridine treated with Utermohlen’s “”sulfo-mix”” (CA 38, 9735) and glycerol gave 30% 1,8-naphthyridine. Similarly were prepared 2-methyl-, 4-methyl-, and 2,4-dimethyl-1,8-naphthyridines (I,II, and III). N.M.R. spectra data are given for the compounds

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Winkley, Michael W.; Robins, Roland K. published the article 《Pyrimidine nucleosides. I. Synthesis of 6-methylcytidine, 6-methyluridine, and related 6-methylpyrimidine nucleosides》. Keywords: pyrimidine nucleosides; nucleosides pyrimidine; cytosines; cytidines; uridines; uracils; ribofuranosyls; methylpyrimidine nucleosides.They researched the compound: 4-Methyl-6-(methylthio)pyrimidin-2-ol( cas:16710-11-5 ).Electric Literature of C6H8N2OS. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:16710-11-5) here.

Synthesis of 6-methylprimidine nucleosides was realized. 6-Methylcytidine (I) and 6-methyl-2′-deoxycytidine were prepared by direct utilization of 6-methylcytosine (II) via silylation and subsequent treatment with the appropriate per-O-acetylglycosyl halide in MeCN. Conversion of I into 6-methyluridine was achieved in 65% yield. This direct glycosylation procedure applied to 6-methyluracil gave 6-methyl-3-(β-D-ribofuranosyl)uracil as the major product. Utilization of this general method resulted in preparation of 5,6-dimethyluridine. A new route to the synthesis of II is reported. 31 references.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Synthesis of 1,8-naphthyridine homologs and their hydrogenation, published in 1941, which mentions a compound: 1569-17-1, Name is 4-Methyl-1,8-naphthyridine, Molecular C9H8N2, Synthetic Route of C9H8N2.

In earlier work (CA 33:2525.5) it was found that Me 1,4-dihydroxy-2,5-naphthyridine-3-carboxylate (C. A. numbering, 5,8-dihydroxy-1,6-naphthyridine-7-carboxylate) and the 1-Cl compound on catalytic hydrogenation take up H only on the nonsubstituted pyridine ring. In continuation of this work, 2,4-dimethyl- (I) and 4-methyl-1,8-naphthyridine (II) have been synthesized and a similar phenomenon on hydrogenation has been observed. In the meantime some other 1,8-naphthyridines described in this paper have been prepared by analogous methods by Mangini (preceding abstract). 7-Amino derivative of I (0.5 g. from 2 g. 2,6-diaminopyridine, 2 g. CH2Ac2 and 1 g. fused ZnCl2 heated 3 hrs. at 120-30°), m. 220° (Ac derivative, pale yellow, m. 300°), converted by diazotization in 40% H2SO4 into the 7-HO compound, m. 251°, which, heated 30 min. in a sealed tube at 140° with POCl3, gives the 7-Cl compound, m. 146-7°; this, boiled 30 min. with 20% MeONa in MeOH, gives the 7-MeO compound, m. 65° (picrate, m. 188-9°). Hydrogenation of 1 g. of the HO compound in 20 g. alc. with 1 g. Ni-kieselguhr under 110 atm. of H for 10 hrs. at 170-80° gave, along with 0.6 g. unchanged material, 0.2 g. of a dihydro derivative, C10H12N2O, m. 175-80°. The Cl compound (0.5 g.), shaken in 10% KOH-MeOH with 0.2 g. of 20% Pd-charcoal and H until about 1.2 mols. H had been absorbed, and the product chromatographed in benzene through Al2O3, yielded about 0.05 g. I, m. 85-6° (HCl salt, decomposes 240°; picrate, decomposes 204-6°; methiodide, yellow needles with 1 H2O, m. 93-4; chloroplatinate, I.H2PtCl6, decomposes 242-4°; chloroaurate, decomposes 166-7°). When 0.1 g. of the Cl compound in 10 cc. of 10% KOH-MeOH was hydrogenated to saturation with 0.5 g. of 20% Pd-charcoal it yielded the tetrahydro derivative (III) of I described below. With 1.2 g. of the Cl compound in 20 cc. of 5% KOH-MeOH, 0.5 g. PdO-CaCO3 and a trace of Pd-charcoal, the hydrogenation stopped in 30 min. (about 170 cc. H absorbed) and 0.8 g. I was obtained. Shaken in 10 cc. AcOH with 0.1 g. Pt oxide and H to saturation, 0.5 g. I absorbed about 160 cc. H and yielded 0.5 g. of a tetrahydro derivative (III), m. 118°, giving a pos. Liebermann reaction (picrate, m. 207°; Ac derivative, m. 42-3°); III was also obtained in 0.85-g. yield from 1 g. I in 50 cc. cyclohexane and 5 cc. alc. with 1 g. Raney Ni heated under an initial H pressure of 70 atm. 2 hrs. at 120° and 2 hrs. at 190°. III was unchanged by 4 hrs. treatment in AcOH with Pt oxide and 110 atm. H pressure, at room temperature With Na in boiling alc., however, it yielded the decahydro derivative of I, easily subliming needles, m. 92-3° (di-Ac derivative, thick oil, b0.02 135-45°). 2,7-Dichloro-4-methyl-1,8-naphthyridine in 10% KOH-MeOH hydrogenated with PdO-CaCO3 and a trace of Pd-charcoal gave, together with a mono-Cl compound, C9H7ClN2, m. 104°, chiefly (about 70%) II, b0.05 147-8° (picrate, decomposes 204-5°; perchlorate, m. 180-1°). II (1 g.) in 10 cc. AcOH with 0.5 g. Pt oxide and H yielded a mixture of 2 isomeric tetrahydro derivatives, separated by fractional crystallization from petr. ether: 0.2 g. of a more soluble isomer A (IV), m. 62-3°, giving a pos. Liebermann reaction (Bz derivative, m. 86-7°), and about 0.8 g. of a less soluble isomer B (V), m. 102-3° (picrate, decomposes 248°; Bz derivative, m. 105-6°; nitro derivative, m. 217-18° and giving a pos. Liebermann reaction, prepared by treating the tetrahydride in cold H2SO4 (dry ice-acetone) with fuming HNO3 (d.1.6), pouring on ice, crystallizing from alc., heating the crystals (m. 124-5°) in concentrated H2SO4 at 60°, again pouring on ice, filtering, making alk. with Na2HPO4 and extracting with ether). V is unchanged by hydrogenation in AcOH with PtO and 65 atm. H pressure. With Na in boiling AmOH, both isomers yield the same (racemic) decahydro derivative of II, b0.1 70-80°, m. 87°, gives a pos. Liebermann reaction (picrate, decomposes 210°). The structures of III, IV and V have not been definitely established but the following considerations make it highly probable what they are. The work of earlier investigators on the hydrogenation of quinoline homologs with Ni and H under pressure and with Sn and HCl has shown that Me groups have a disturbing influence on the hydrogenation of the ring half on which they are substituted whereas Na and alc. readily hydrogenate the Me-substituted rings. This disturbing effect of Me groups is ascribed to the inductive effect of the Me group. III is considered to be the 5,6,7,8-tetrahydro compound To further confirm this, III was heated in a little alc. with an excess of ClCH2COMe for 4 hrs. at 100°; the resulting addition product, C15H21ClN22O2, m. 181-2°, allowed to stand 1 day in a little water with 2 drops of 10% Na3CO3, gave, in addition to unchanged III, a resin whose blue Ehrlich reaction pointed to the presence of an indolizine ring. Such a ring can be formed only from a nonhydrogenated 2-methylpyridine. IV is considered to be the 1,2,3,4- and V the 5,6,7,8-tetrahydro compound because the latter is formed in the larger amount; its higher m. p. is also in harmony with such an assumption.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Category: naphthyridine. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 4-Methyl-1,8-naphthyridine, is researched, Molecular C9H8N2, CAS is 1569-17-1, about New catalytic systems for 2,6-dimethylphenol polycondensation. Author is Sacconi, Luigi; Foa, Marco; Bencini, Elena; Nocci, Roberto; Sabarino, Giampiero.

Catalytic systems based on dimeric Cu complexes with imidazole as bridging unit and on Cu naphthyridine complexes for polymerization of 2,6-dimethylphenol were described. The polymerization conditions, e.g., nature and amount of free amine added, solvent, etc., were studied to get a polymer of suitable mol. weight

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

HPLC of Formula: 91523-50-1. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid, is researched, Molecular C10H11NO3, CAS is 91523-50-1, about Gas chromatography mass spectrometry analysis and in vitro antibacterial activity of essential oil from Trigonella foenum-graecum. Author is Moniruzzaman; Shahinuzzaman; Haque, Ahsanul; Khatun, Rahima; Yaakob, Zahira.

Objective: To evaluate the antibacterial activity of essential oil from Trigonella foenum-graecum seeds powder, and identify the compounds from the extracted oil. Methods: The seeds powder of Trigonella foenum-graecum was subjected to Clevenger extractor. Seven strains of bacteria were used to test antibacterial activity of the extract The activity against bacteria was tested by disk diffusion method using Whatman Number1 filter paper. Gas chromatog. mass spectrometry anal. was performed with an Agilent7890/5975B-gas chromatog./mass selective detector. Results: The hydrodistillation of seeds powder yielded 0.285% (v/w) of oil. Disk diffusion of the oil showed bactericidal activity against both Gram neg. and Gram pos. bacteria of lasted strains. The inhibition zone ranged from (8 ± 0) mm to (15.0 ± 0.7) mm depending on microbial strains. Gas chromatog. mass spectrometry anal. showed 14 different compounds The total compounds represented 80.96% of the oil. Conclusions: The antibacterial activity is due to the effects of different biol. active compounds present in the extract Identification of the compounds may help to develop new effective antimicrobial agent(s). Further researches on purification, characterization and toxicol. of the active compounds are needed.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Sacconi, Luigi; Foa, Marco; Bencini, Elena; Nocci, Roberto; Sabarino, Giampiero published the article 《New catalytic systems for 2,6-dimethylphenol polycondensation》. Keywords: copper complex polymerization catalyst dimethylphenol; imidazole copper polymerization catalyst dimethylphenol; naphthyridine copper polymerization catalyst dimethylphenol; polydimethylphenol copper complex polymerization catalyst.They researched the compound: 4-Methyl-1,8-naphthyridine( cas:1569-17-1 ).Recommanded Product: 4-Methyl-1,8-naphthyridine. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:1569-17-1) here.

Catalytic systems based on dimeric Cu complexes with imidazole as bridging unit and on Cu naphthyridine complexes for polymerization of 2,6-dimethylphenol were described. The polymerization conditions, e.g., nature and amount of free amine added, solvent, etc., were studied to get a polymer of suitable mol. weight

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Journal of Organic Chemistry called Nuclear magnetic resonance studies on σ-adducts of heterocyclic systems with nucleophiles. 18. Proton and carbon-13 nuclear magnetic resonance investigations on σ-adduct formation between 1,X-naphthyridines and some methyl-1,8-naphthyridines with potassium amide in liquid ammonia, Author is Van der Plas, H. C.; Van Veldhuizen, A.; Wozniak, M.; Smit, P., which mentions a compound: 1569-17-1, SMILESS is CC1=C2C=CC=NC2=NC=C1, Molecular C9H8N2, Category: naphthyridine.

The 1,5-, 1,6-, and 1,8-naphthyridines dissolved in liquid NH3 containing KNH2 showed the H-2 and C-2 resonance at about 4 and 90 ppm higher field, resp., than the H-2 and C-2 resonance of the naphthyridines observed in CDCl3 as NH2- added to all 3 naphthyridines at C-2 to give a 2-amino-1,2-dihydro-1,X-naphthyridinide ion. The 1,7-naphthyridine showed a more complex reactivity pattern toward NH2-. Besides addition at C-2, addition at C-6 and at C-8 is observed The relation of this study with that of the Chichibabin amination of the 1,X-naphthyridines is discussed. NH2- and 2-methyl- and 4-methyl-1,8-naphthyridine gave only deprotonation of the Me group; 3-methyl-1,8-naphthyridine and NH2- gave the 2-amino-1,2-dihydro-3-methyl-1,8-naphthyridinide ion.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

COA of Formula: C10H11NO3. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid, is researched, Molecular C10H11NO3, CAS is 91523-50-1, about Synthesis of novel (benzimidazolyl)isoquinolinols and evaluation as adenosine A1 receptor tools. Author is Singh, Sameek; Cooper, Samantha L.; Glenn, Jacqueline R.; Beresford, Jessica; Percival, Lydia R.; Tyndall, Joel D. A.; Hill, Stephen J.; Kilpatrick, Laura E.; Vernall, Andrea J..

G protein-coupled receptors (GPCRs) constitute the largest family of transmembrane receptors in eukaryotes. The adenosine A1 receptor (A1AR) is a class A GPCR that is of interest as a therapeutic target particularly in the treatment of cardiovascular disease and neuropathic pain. Increased knowledge of the role A1AR plays in mediating these pathophysiol. processes will help realize the therapeutic potential of this receptor. There is a lack of enabling tools such as selective fluorescent probes to study A1AR, therefore we designed a series of (benzimidazolyl)isoquinolinols conjugated to a fluorescent dye (31-35, 42-43). An improved procedure for the synthesis of isoquinolinols from tetrahydroisoquinolinols via oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and atm. oxygen is reported. This synthetic method offers advantages over previous metal-based methods for the preparation of isoquinolinols and isoquinolines, which are important scaffolds found in many biol. active compounds and natural products. We report the first synthesis of the (benzimidazolyl)isoquinolinol compound class, however the fluorescent conjugates were not successful as A1AR fluorescent ligands.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem