Tag: M.W:100-200

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 Vicarious nucleophilic substitution of hydrogen, bisannulation and competitive reactions of α-haloalkyl carbanions with bicyclic azaaromatic compounds, published in 1991-03-31, which mentions a compound: 1569-17-1, Name is 4-Methyl-1,8-naphthyridine, Molecular C9H8N2, Electric Literature of C9H8N2.

Carbanions of RR1CHSO2R2 (I; R = Cl, R1 = H, Me, R2 = NMe2, Ph, CMe3, morpholino, tolyl; R = Br, R1 = H, R2 = tolyl) react with bicyclic heteroaromatic compounds (quinoxalines, naphthyridines, and 5-azaquinoxalines) according to 2 general pathways: vicarious nucleophilic substitution (VNS) of hydrogen and/or bisannulation. In some cases other competitive reactions are observed Factors governing the direction of these reactions are discussed in terms of the charge distribution in the anionic σ adducts and the reaction conditions. For example reaction of quinoxaline and quinoxaline N-oxide with I (R = Cl, R1 = H, R2 = Ph) gave bisazirinoquinoxaline II and VNS product III resp.

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

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 4-Methyl-6-(methylthio)pyrimidin-2-ol( cas:16710-11-5 ) is researched.Application In Synthesis of 4-Methyl-6-(methylthio)pyrimidin-2-ol.Erkin, A. V.; Krutikov, V. I. published the article 《4-arylamino-2-(2-acetoxyethyl)amino-6-methylpyrimidines: Synthesis, deacetylation, and biological activity》 about this compound( cas:16710-11-5 ) in Russian Journal of General Chemistry. Keywords: ethanolamine acetate arylaminopyrimidinyl tuberculostatic preparation; pyrimidinediamine acetoxyethyl aryl tuberculostatic preparation; deacetylation acetoxyethylaminopyrimidine. Let’s learn more about this compound (cas:16710-11-5).

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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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, RSC Advances called 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., which mentions a compound: 91523-50-1, SMILESS is OC(=O)C1NCCC2=C1C=CC(O)=C2, Molecular C10H11NO3, Recommanded Product: 91523-50-1.

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

Computed Properties of C9H8N2. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 4-Methyl-1,8-naphthyridine, is researched, Molecular C9H8N2, CAS is 1569-17-1, about 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..

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

Computed Properties of C9H8N2. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 4-Methyl-1,8-naphthyridine, is researched, Molecular C9H8N2, CAS is 1569-17-1, about Syntheses of nitrogen-containing compounds. XVII. Improvement of one-step synthesis of naphthyridine derivatives and their methylation with demethyl sulfoxide in the presence of base. Author is Hamada, Yoshiki; Takeuchi, Isao; Hirota, Minoru.

1,8-Naphthyridines were synthesized in a high yield by the reaction of 2-aminopyridines with glycerol, in the presence of Na m-nitrobenzenesulfonate, in H2SO4. Methylation of naphthyridines with Me2SO in the presence of NaH or KOBu-tert afforded their mono-Me or di-Me compounds This methylation with methylsulfinyl carbanion was examined from the Hueckel MO method; the calculation agreed with the exptl. results.

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1,8-Naphthyridine | C8H6N2 – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 4-Methyl-1,8-naphthyridine, is researched, Molecular C9H8N2, CAS is 1569-17-1, about A one-pot method for the synthesis of naphthyridines via modified Friedlander reaction, the main research direction is naphthyridine preparation; pyridinamine acrolein Friedlander cyclocondensation.COA of Formula: C9H8N2.

A one-pot method for the preparation of 1,8-naphthyridine derivatives is reported. The method involves the dimetalation of an appropriate N-2-pyridylpivalamide or tert-butylcarbamate followed by reaction with a β-dimethylamino- or β-alkoxyacrolein derivative This method is also applicable to 1,6-naphthyridines.

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

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 4-Methyl-1,8-naphthyridine( cas:1569-17-1 ) is researched.Synthetic Route of C9H8N2.Wozniak, Marian published the article 《Hydrogen-deuterium exchange in 1,8-naphthyridine and some its monosubstituted derivatives》 about this compound( cas:1569-17-1 ) in Zeszyty Naukowe Uniwersytetu Jagiellonskiego, Prace Chemiczne. Keywords: naphthyridine derivative hydrogen deuterium exchange; substituent effect hydrogen exchange naphthyridine. Let’s learn more about this compound (cas:1569-17-1).

Hydrogen-deuterium exchange in 1,8-naphthyridine and 10 of its derivatives containing Me, hydroxy, amino, nitro and chloro substituents are reported. A discussion of the factors influencing the relative positional reactivity toward deuterium in these compounds is presented.

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

Recommanded Product: 1569-17-1. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 4-Methyl-1,8-naphthyridine, is researched, Molecular C9H8N2, CAS is 1569-17-1, about Kinetics of quaternization of some naphthyridines and methylnaphthyridines. Author is Jones, Richard A. Y.; Wagstaff, Nigel.

The 2nd order rate constants for the reaction of MeI with some naphthyridines and methylnaphthridines in MeCN were determined by a conductimetric method. The following results were obtained at 24.8° (compound, and rate constant × 10-4 l./mole/sec. given): quinoline, 0.517; isoquinoline, 4.23; 1,5-naphthyridine, 0.232; 1,6-naphthyridine, 1.66; 1,8-naphthyridine, 4.25; 2-methyl-1,8-naphthyridine, 3.61; 3-methyl-1,8-naphthyridine, 5.74; 4-methyl-1,8-naphthyridine, 7.26; and 2,7-dimethyl-1,8-naphthyridine, 1.85. The rate constants are used to deduce the quaternization kinetics of the reactions.

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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: 91523-50-1, is researched, SMILESS is OC(=O)C1NCCC2=C1C=CC(O)=C2, Molecular C10H11NO3Conference, Applied Biocatalysis called Chemo-enzymatic synthesis of (S)-1,2,3,4-tetrahydroisoquinoline carboxylic acids using D-amino acid oxidase, Author is Ju, Shuyun; Qian, Mingxin; Xu, Gang; Yang, Lirong; Wu, Jianping, the main research direction is tetrahydroisoquinoline carboxylic acid FsDAAO catalyst enantioselective enzymic resolution; chiral tetrahydroisoquinoline carboxylic acid preparation.HPLC of Formula: 91523-50-1.

In this context, an (R)-selective D-amino acid oxidase from Fusarium solani M-0718 (FsDAAO) with broad substrate scope and excellent enantioselectivity was found through genome mining. This enzyme was applied for the kinetic resolution of a range of racemic 1- and 3-carboxyl substituted THIQs with different substitutions on the aryl rings. Preparative-scale deracemization of racemic 1,2,3,4- tetrahydroisoquinoline-1-carboxylic acid and 1,2,3,4-tetrahydroisoquinoline-3- carboxylic acid was further demonstrated.

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

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Syntheses of naphthyridine derivatives. IV. Syntheses of 1,8-naphthyridines and their hydrogenation, published in 1942, which mentions a compound: 1569-17-1, mainly applied to , HPLC of Formula: 1569-17-1.

Heating 10 g. 2,6-diaminopyridine (I) and 14 g. freshly distilled AcCH2CO2Et at 145-50° 2 h. and taking up with alc. gives 6.5 g. solid, 5 g. of which is taken up in 60 mL. 33% H2SO4, ice-cooled, 3 g. saturated NaNO2 solution added, the mixture let stand 1 h., poured into 150 mL. boiling water, filtered after cooling, the product taken up in hot aqueous NaOH, filtered after cooling, and acidified with HCl, giving 2,7-dihydroxy-4-methyl-1,8-naphthyridine (II), white needles, m. above 350°. I and AcCH2COMe (equimol. amounts) do not condense on heating up to 135°; addition of ZnCl2 and heating at 120-30° 3 h. gives a solid product, which, treated with NaOH, taken up with CHCl3, and extracted with AcOEt, yields 2,4-dimethyl-7-amino-1,8-naphthyridine (III), columns, m. 220°; III with HNO2 gives the 7-HO analog (IV), columns, m. 251°. Heating IV and POCl3 in a sealed tube at 140° 30 min., decomposing with ice, and treating with NaOH to pH 8 gives the 7-Cl analog (V), needles, m. 146-7°. Dehalogenation by catalytic hydrogenation of V in MeOH-KOH with Pd-C gives the 5,6,7,8-tetrahydride (VI), needles, m. 118°, and with Pd-CaCO3 2,4-dimethyl-1,8-naphthyridine (VII), needles, m. 85-6°. Boiling of V with MeONa-MeOH 30 min., removing the MeOH, adding water, taking up with AcOEt, and recrystallizing from petr. ether gives the 7-MeO compound (VIII), prisms, m. 65°; picrate, columns, m. 188-9°. Treating II with POCl3 in a sealed tube at 150° 20 min., pouring on ice, making alk. with NaOH, and recrystallizing from Me2CO give 2,7-dichloro-4-methyl-1,8-naphthyridine (IX), columns, m. 194°. Catalytic dehalogenation of IX with Pd-CaCO3 gives ether-petr. ether insoluble and soluble portions; the insoluble portion gives a mono-Cl derivative, needles, m. 104°; the soluble portion gives 4-methylnaphthyridine (X), b0.05 130-40° (picrate, columns, m. 207°). Tetrahydride of VII, columns, m. 118° (picrate, columns, m. 207°; acetate, white, m. 42-3°). Catalytic reduction of 4-methyl-1,8-naphthyridine with PtO gives a petr. ether-insoluble portion, m. 102-3°, and a soluble portion, m. 62-3°, both tetrahydrides.

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