Month: April 2022

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).Product Details 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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1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Application of 2689-65-8. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about 1H-Indenylfuran and -thiophene derivatives: a new class of singlet-oxygen sensitizers.

Photophys. and photochem. properties of title compounds I (X = O, S; R = H, Me) and II (R = H, inden-2-yl) were studied. All the compounds absorbed UV light at 350-380 nm. The fluorescence spectra of I and II showed bands at 410-470 nm and quantum yields in the range 0.25-0.88. Attempts to calculate the triplet energy failed except for I (X = S, R = Me) and II (R = H), which showed ET = 43-44 kcal mol-1. These compounds are a new class of singlet-oxygen sensitizers. The sensitized reaction of 2,5-dimethylfuran with singlet oxygen was followed. I (X = O, R = H) and II (R = inden-2-yl) are more reactive than α-terthiophene (III), while the other compounds show the same reactivity as III. This behavior can be explained by different intersystem crossing quantum yields. Diazabicyclo[2.2.2]octane is a quencher of singlet oxygen in this reaction. Superoxide ion formation is excluded by photooxidation of α,α’-dimethylstilbene.

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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 《Action of Methyl Iodide and of Benzyl Chloride upon 2-Oxy-4-methyl-6-methylmercaptopyrimidine》. Authors are Wheeler, Henry L.; Mcfarland, David F..The article about the compound:4-Methyl-6-(methylthio)pyrimidin-2-olcas:16710-11-5,SMILESS:CSC1=NC(O)=NC(C)=C1).Application In Synthesis of 4-Methyl-6-(methylthio)pyrimidin-2-ol. Through the article, more information about this compound (cas:16710-11-5) is conveyed.

2-Methylmercapto-4-methyl-6-chloropyrimidine, C6H7N2ClS, was made from the oxypyrimidine and PCl5, b32-5 147°, m. 39-40°. This with KSH gave 2-methylmercapto-4-methyl-6-thiopyrimidine, C6H8N2S2, m. 214°, heating at 215-23° gave 2,6-dithio-4-methyluracil. Boiling the mercapto compound with HCl formed 6-thio-4-methyluracil, C6H6ON2S, prisms decompose above 250°, which with NaOH and MeI gives 2-oxy-4-methyl-6-methylmercaptopyrimidine, C6H8ON2S, needles, m. 174-5°. The mercaptopyrimidine with NaOH and PhCH2Cl yielded after treatment with HCl a mixture of 1-benzyl and 3-benzyluracil. The methylation of 2-oxy-4-methyl-6-methylmercaptopyrimidine gave 2-oxy-3,4-dimethyl-6-methylmercaptopyrimidine, C7H10ON2S, m. 170-1° and probably the 1,4-dimethyl product not isolated. 2-Oxy-4-methyl-6-o-nitrobenzylmercaptopyrimidine, m. 205°. 2-Oxy-4-methyl-6-m-dinitrophenylmercaptopyrimidine, m. 208°.

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

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 2689-65-8, is researched, Molecular C5H3IO2, about Site-Selective C-S Bond Formation at C-Br over C-OTf and C-Cl Enabled by an Air-Stable, Easily Recoverable, and Recyclable Palladium(I) Catalyst, the main research direction is carbon sulfur bond formation palladium catalyst aryl halide thiolation; chemoselectivity; dinuclear catalysis; homogeneous catalysis; palladium; thiolation.Category: naphthyridine.

This report widens the repertoire of emerging PdI catalysis to carbon-heteroatom, i.e., C-S bond formation. While Pd0-catalyzed protocols may suffer from the formation of poisonous sulfide-bound off-cycle intermediates and lack of selectivity, the mechanistically diverse PdI catalysis concept circumvents these challenges and allows for C-S bond formation (S-aryl and S-alkyl) of a wide range of aryl halides. Site-selective thiolations of C-Br sites in the presence of C-Cl and C-OTf were achieved in a general and a priori predictable fashion. Computational, spectroscopic, x-ray, and reactivity data support dinuclear PdI catalysis to be operative. Contrary to air-sensitive Pd0, the active PdI species was easily recovered in the open atm. and subjected to multiple rounds of recycling.

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

Computed Properties of C5H3IO2. 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: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about Study of the nucleophilic substitution of halogens in furan compounds. (I). Furfurals. Author is Mocelo, R.; Pustovarov, V..

5-Bromofurfural (I, R = Br) was prepared by treating I (R = H) in dichloroethane with Br in the presence of hydroquinone. Reaction of I (R = Br) with LiCl in DMF gave 74% I (R = Cl) and with KI-HOAc gave 80% I (R = I). I (R = I) was similarly obtained in 44% yield from I (R = Cl). I (R = Cl) could also be converted to I (R = Br) with KBr-HOAc.

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

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2-Bromo-1-(1-methyl-1H-pyrrol-2-yl)ethanone(SMILESS: CN1C(C(CBr)=O)=CC=C1,cas:65438-97-3) is researched.Safety of 4-Methyl-1,8-naphthyridine. The article 《Design, synthesis and biological activities of benzo[d]imidazo[1,2-a]imidazole derivatives as TRPM2-specific inhibitors》 in relation to this compound, is published in European Journal of Medicinal Chemistry. Let’s take a look at the latest research on this compound (cas:65438-97-3).

Transient receptor potential melastatin 2 (TRPM2) channel is associated with ischemia/reperfusion injury, inflammation, cancer and neurodegenerative diseases. However, the lack of specific inhibitors impedes the development of TRPM2 targeted therapeutic agents. To develop a selective TRPM2 inhibitor, three-dimensional similarity-based screening strategy was employed using the energy-minimized conformation of non-selective TRPM2 inhibitor 2-APB as the query structure, which resulted in the discovery of a novel tricyclic TRPM2 inhibitor I with benzo[d]imidazo[1,2-a]imidazole skeleton. A series of I derivatives were subsequently synthesized and evaluated using calcium imaging and electrophysiol. approaches. Among them, preferred compounds II and III inhibited the TRPM2 channel with micromolar half-maximal inhibitory concentration values and exhibited TRPM2 selectivity over the TRPM8 channel, TRPV1 channel, InsP3 receptor and Orai channel. The anal. of structure-activity relationship provides valuable insights for further development of selective TRPM2 inhibitors. Neuroprotection assay showed that II and III could effectively reduce the mortality of SH-SY5Y cells induced by H2O2. These findings enrich the structure types of existing TRPM2 inhibitors and might provide a new tool for the study of TRPM2 function in Reactive oxygen species (ROS) -related diseases.

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

Safety of 4-Methyl-1,8-naphthyridine. 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 Hydrogen-deuterium exchange in 1,8-naphthyridine and some its monosubstituted derivatives. Author is Wozniak, Marian.

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

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 Novel Allosteric Ligands of γ-Aminobutyric Acid Transporter 1 (GAT1) by MS Based Screening of Pseudostatic Hydrazone Libraries, the main research direction is nipecotic acid pseudostatic hydrazone library preparation GAT1 allosteric ligand.Computed Properties of C5H3IO2.

This study describes the screening of dynamic combinatorial libraries based on nipecotic acid as core structure with substituents attached to the 5- instead of the common 1-position for the search of novel inhibitors of the GABA transporter GAT1. The generated pseudostatic hydrazone libraries included a total of nearly 900 compounds and were screened for their binding affinities toward GAT1 in competitive mass spectrometry (MS) based Binding Assays. Characterization of the hydrazones with the highest affinities (with cis-configured compound I bearing a 5-(1-naphthyl)furan-2-yl residue and a four atom spacer being the most potent) in binding and uptake experiments revealed an allosteric interaction at GAT1, which was not reported for any other nipecotic acid derivative up to now. Therefore, the herein introduced 5-substituted nipecotic acid derivatives could serve as valuable tools for investigations of allosterically modulated GABA transport mediated by GAT1 and furthermore as starting point for a new class of GAT1 inhibitors.

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

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Osipov, O. A.; Sheinker, V. N.; Kuzharov, A. S.; Nazarova, Z. N.; Derecha, E. G.; Bulgarevich, S. B. researched the compound: 5-Iodo-2-furaldehyde( cas:2689-65-8 ).Related Products of 2689-65-8.They published the article 《Structure and properties of heterocyclic compounds and complexes. III. Conformations of substituted furfurals studied by dipole moments and Kerr effect methods》 about this compound( cas:2689-65-8 ) in Zhurnal Obshchei Khimii. Keywords: furfural conformation dipole; dipole moment furfural; Kerr effect furfural. We’ll tell you more about this compound (cas:2689-65-8).

Conformational equilibrium of 3-bromo-, 5-bromo-, 4,5-dibromo-, 3-methyl-, 5-methyl-, 5-iodo-, and 5-nitro-2-furaldehyde were determined Substituent repulsion energy played a significant role in determining relative conformational stabilities.

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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 3-(5-X-2-Furyl)-2-cyanoacrylonitriles on reaction with 2-cyanomethylbenzothiazole, published in 1991-02-28, which mentions a compound: 2689-65-8, Name is 5-Iodo-2-furaldehyde, Molecular C5H3IO2, Product Details of 2689-65-8.

2-Cyanomethylbenzothiazole reacts with 3-(5-substituted 2-furyl)-, 3-(2-thienyl)- or 3-(2-pyrrolyl)-2-cyanoacrylonitrile in THF under catalysis of triethylamine to give 1-(2-benzothiazolyl)-1-acyano-2-heteroarylethylenes e.g. I (R = H, X = O, S, NH; R = Br, Me, NO2, X = O) as a result of replacement of malonodinitrile by 2-cyanomethylbenzothiazole.

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