Heterocyclic Building Blocks-Naphthyridine

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.HPLC of Formula: 1569-17-1.Sacconi, Luigi; Foa, Marco; Bencini, Elena; Nocci, Roberto; Sabarino, Giampiero published the article 《New catalytic systems for 2,6-dimethylphenol polycondensation》 about this compound( cas:1569-17-1 ) in Chimica e l’Industria (Milan, Italy). Keywords: copper complex polymerization catalyst dimethylphenol; imidazole copper polymerization catalyst dimethylphenol; naphthyridine copper polymerization catalyst dimethylphenol; polydimethylphenol copper complex polymerization catalyst. Let’s learn more about this compound (cas:1569-17-1).

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

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about A new approach to furan-containing macrolactones.Reference of 5-Iodo-2-furaldehyde.

Furan and THF heterocycles are part of many natural products, like the Galerucella pheromone, furano epothilones, bipinnatin, and amphidinolides. This paper describes a short and efficient synthetic approach to furan-containing macrolactones in 4 steps, including as key steps a Sonogashira reaction and an olefin metathesis. The resulting compounds were tested at the National Cancer Institute for their cytotoxicity, but did not exhibit significant cytotoxicity in the human tumor cell line screen.

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

Safety of 5-Iodo-2-furaldehyde. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about Electrochemically Promoted Nickel-Catalyzed Carbon-Sulfur Bond Formation. Author is Wang, Yang; Deng, Lingling; Wang, Xiaochen; Wu, Zhengguang; Wang, Yi; Pan, Yi.

This work describes a nickel-catalyzed Ullmann-type thiolation of aryl iodides under mild electrochem. conditions. The simple undivided cell with graphite felt/nickel foam electrode setups offers excellent substrate tolerance, affording aryl and alkyl sulfides in good chem. yields. Furthermore, the mechanism for this electrochem. cross-coupling reaction has been investigated by cyclic voltammetry.

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

Ballester, L.; Caballero, B.; Fernandez Bertran, J.; Gra, R. published the article 《Study of the first harmonic of the carbonyl stretching vibration of furfural and 5-substituted derivatives》. Keywords: IR furfural solvent effect; LFER furfural carbonyl stretch.They researched the compound: 5-Iodo-2-furaldehyde( cas:2689-65-8 ).Application In Synthesis of 5-Iodo-2-furaldehyde. 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:2689-65-8) here.

The solvent effect on the frequencies of the 1st harmonic of the CO group stretching vibrations in furfural and its 5-NO2, 5-Br, 5-I, 5-Me, or 5-Me2N derivatives was examined The transitions were assigned to the 00 cis and 00 trans rotamers. The 5-substituent affected the CO stretch analogously to the effects of p-substituents on the CO stretch in BzH; the rotamer CO stretching frequencies showed a LFER with σp.

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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 Spectral data of substituted naphthyridines. V. The IR spectra of substituted 1,8-naphthyridines, published in 1979, which mentions a compound: 1569-17-1, Name is 4-Methyl-1,8-naphthyridine, Molecular C9H8N2, SDS of cas: 1569-17-1.

In general the IR spectra of 1,8-naphthyridines show a ring bending (skeletal) vibration at 690-740-cm-1, three adjacent H absorption at 750-795 and 810-885 cm-1, two adjacent H absorptions at 785-855 cm-1 and isolated H absorptions at 795-810 and 885-920 cm-1.

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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 Synthesis and nanoparticle encapsulation of 3,5-difuranylvinyl-boradiaza-s-indacenes for near-infrared fluorescence imaging, published in 2009-05-28, which mentions a compound: 2689-65-8, mainly applied to nanoparticle encapsulation furanylvinyl boradiazaindacene dye near IR fluorescence imaging; singlet oxygen generation furanylvinyl boradiazaindacene, Recommanded Product: 2689-65-8.

The mol. design, synthesis, and photophys. study of a series of near-IR absorbing and fluorescing dyes, 3,5-difuranylvinyl-boradiaza-s-indacenes, bearing various 5-membered heteroaromatic heads at the 8-position (FBs) are reported. The correlation between the mol. structure and the spectral shift has been studied by quantum chem. calculations at various levels (B3LYP/6-31G*, HF/6-31G* and HF/PM3), which conclude that the planarity determined by the bulkiness of the head unit controls the optical band gap of FBs, by energetically affecting the LUMO rather than the HOMO. It was also shown that incorporation of heavy atoms increased the capability of singlet oxygen generation as a result of enhanced intersystem crossing, which makes FBs potentially useful for near-IR photodynamic therapy. In vitro near-IR fluorescence imaging of live tumor cells has been demonstrated through a nanocarrier approach, by encapsulating one of the FB dyes in a stable aqueous formulation of organically modified silica nanoparticles which retains the fluorescence efficiency of the hydrophobic dye in water.

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

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about Direct Synthesis of Water-Tolerant Alkyl Indium Reagents and Their Application in Palladium-Catalyzed Couplings with Aryl Halides, the main research direction is alkyl halide indium insertion reaction; water tolerant alkyl indium reagent preparation coupling aryl halide.Formula: C5H3IO2.

A mild, efficient and straightforward method for the synthesis of water-tolerant alkyl indium reagent through CuCl-mediated direct insertion of indium into alkyl halide in THF at room temperature is described.

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

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 4-Methyl-6-(methylthio)pyrimidin-2-ol, is researched, Molecular C6H8N2OS, CAS is 16710-11-5, about Pyrimidine nucleosides. I. Synthesis of 6-methylcytidine, 6-methyluridine, and related 6-methylpyrimidine nucleosides, the main research direction is pyrimidine nucleosides; nucleosides pyrimidine; cytosines; cytidines; uridines; uracils; ribofuranosyls; methylpyrimidine nucleosides.Recommanded Product: 16710-11-5.

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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1,8-Naphthyridine | C8H6N2 – PubChem

Recommanded Product: 2-Bromo-1-(1-methyl-1H-pyrrol-2-yl)ethanone. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2-Bromo-1-(1-methyl-1H-pyrrol-2-yl)ethanone, is researched, Molecular C7H8BrNO, CAS is 65438-97-3, about Visible-Light-Mediated Addition of Phenacyl Bromides onto Cyclopropenes. Author is Dange, Nitin S.; Hussain Jatoi, Ashique; Robert, Frederic; Landais, Yannick.

In the presence of the photocatalyst fac-Ir(ppy)3 (ppy = 2-pyridinylphenyl), K2CO3, and LiBr in DMF, aryl bromomethyl ketones such as phenacyl bromide underwent chemoselective photochem. addition and cyclization reactions with cyclopropenecarboxylates such as I under irradiation with blue LED at 0° followed by base-mediated ring opening at 60° without irradiation to give oxonaphthaleneacetates such as II and oxobenzo-fused heterocyclylacetates in 16-51% yields. Nonracemic II was prepared in 40% yield and 95:5 er by the reaction of nonracemic I (95:5 er) with phenacyl bromide. Oxonaphthaleneacetates derived from this reaction can be further converted in one or two steps to polycyclic products such as naphthopyranacetate III and benzoindeneacetate IV.

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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 《Syntheses of naphthyridine derivatives. IV. Syntheses of 1,8-naphthyridines and their hydrogenation》. Authors are Miyagi, Komei.The article about the compound:4-Methyl-1,8-naphthyridinecas:1569-17-1,SMILESS:CC1=C2C=CC=NC2=NC=C1).Application of 1569-17-1. Through the article, more information about this compound (cas:1569-17-1) is conveyed.

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