Month: April 2022

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: 4-Methyl-1,8-naphthyridine, is researched, Molecular C9H8N2, CAS is 1569-17-1, about Kinetics of quaternization of some naphthyridines and methylnaphthyridines.Product Details of 1569-17-1.

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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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, Heterocycles called An unusual photochemical reaction of indene with furan and thiophene derivatives, Author is D’Auria, Maurizio; De Mico, Antonella; D’Onofrio, Franco, which mentions a compound: 2689-65-8, SMILESS is IC1=CC=C(O1)C=O, Molecular C5H3IO2, SDS of cas: 2689-65-8.

Photochem. substitution of iododfurans or iodothiophenes by indene gave 2-indenylfurans or -thiophenes. E.g., irradiation of 5-iodofuran-2-carboxaldehyde in MeCN in the presence of indene gave the substitution product I.

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Reference:
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 based on formylfuro(2,3-b) benzothiachromone, published in 1974, which mentions a compound: 2689-65-8, mainly applied to furobenzothiachromone, Safety of 5-Iodo-2-furaldehyde.

ο[(5-Formyl-2-furyl)thio]-benzoic acid, obtained from reaction of ο-mercaptobenzoic acid with 5-iodofurfural, cyclized (polyphosphoric acid) to give the furobenzothiachromone I (R = CHO), which when treated with HONH2 gave I (R = CH:NOH). The latter was converted (Ac2O) to the nitrile I (R = CN), hydrolysis (polyphosphoric acid) of which gave the expected amide I (R = CONH2).

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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 《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).Electric Literature of C9H8N2. 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

HPLC of Formula: 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 Spectral data of substituted naphthyridines. V. The IR spectra of substituted 1,8-naphthyridines. Author is Wozniak, Marian; Roszkiewicz, Witold.

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

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 Furan derivatives. XLVI. Infrared spectra of substituted 2-furyl cyanides.Category: naphthyridine.

The spectral data of the cyanides I (R = H, halo, Me, NO2, AcO) in CHCl3 and CCl4 were given and the influence of substituents and solvents on the wave numbers and integrated absorption intensities of the ν(CN) bands discussed. Wave numbers of the ν(CN) bands increased with increasing electron-acceptor ability of the substituents; the wave numbers were higher than those of the corresponding substituted Ph cyanides. Integrated absorption intensities of the ν(CN) bands decreased with increasing electron-acceptor ability of the substituents and were more significantly influenced by the nature of the substituents and the polarity of the solvents than the wave numbers of these bands.

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

Safety of 5-Iodo-2-furaldehyde. 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: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about Ligand-Promoted Meta-C-H Arylation of Anilines, Phenols, and Heterocycles. Author is Wang, Peng; Farmer, Marcus E.; Huo, Xing; Jain, Pankaj; Shen, Peng-Xiang; Ishoey, Mette; Bradner, James E.; Wisniewski, Steven R.; Eastgate, Martin D.; Yu, Jin-Quan.

The authors report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic aryl iodides as coupling partners is also realized for the first time using this ligand. The utility for this transformation for drug discovery is showcased by allowing the meta-C-H arylation of a lenalidomide derivative The first steps toward a silver-free protocol for this reaction are also demonstrated.

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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 Improving the Solubility of Artificial Ligands of Streptavidin to Enable More Practical Reversible Switching of Protein Localization in Cells.Name: 5-Iodo-2-furaldehyde.

Chem. inducers that can control target-protein localization in living cells are powerful tools to investigate dynamic biol. systems. We recently reported the retention using selective hook or “”RUSH”” system for reversible localization change of proteins of interest by addition/washout of small-mol. artificial ligands of streptavidin (ALiS). However, the utility of previously developed ALiS was restricted by limited solubility in water. Here, we overcame this problem by X-ray crystal structure-guided design of a more soluble ALiS derivative (ALiS-3), which retains sufficient streptavidin-binding affinity for use in the RUSH system. The ALiS-3-streptavidin interaction was characterized in detail. ALiS-3 is a convenient and effective tool for dynamic control of a-mannosidase II localization between ER and Golgi in living cells.

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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 Furan derivatives. XLVI. Infrared spectra of substituted 2-furyl cyanides, published in 1975, which mentions a compound: 2689-65-8, Name is 5-Iodo-2-furaldehyde, Molecular C5H3IO2, COA of Formula: C5H3IO2.

The spectral data of the cyanides I (R = H, halo, Me, NO2, AcO) in CHCl3 and CCl4 were given and the influence of substituents and solvents on the wave numbers and integrated absorption intensities of the ν(CN) bands discussed. Wave numbers of the ν(CN) bands increased with increasing electron-acceptor ability of the substituents; the wave numbers were higher than those of the corresponding substituted Ph cyanides. Integrated absorption intensities of the ν(CN) bands decreased with increasing electron-acceptor ability of the substituents and were more significantly influenced by the nature of the substituents and the polarity of the solvents than the wave numbers of these bands.

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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 Stereospecific Synthesis of Tri- and Tetrasubstituted α-Fluoroacrylates by Mizoroki-Heck Reaction, published in 2016-02-05, which mentions a compound: 2689-65-8, mainly applied to stereospecific trisubstituted tetrasubstituted fluoroacrylate preparation; palladium catalyzed Mizoroki Heck reaction fluoroacylate aryl heteroaryl iodide; fluorinated analog therapeutic agent preparation Mizoroki Heck reaction, Category: naphthyridine.

Ligand-free, efficient, palladium-catalyzed Mizoroki-Heck reaction between Me α-fluoroacrylate and arene or hetarene iodides is reported for the first time. The reaction is stereospecific and provides fair to quant. yields of fluoroalkenes. The Mizoroki-Heck reaction starting from more hindered and usually reluctant trisubstituted acrylate, to access tetrasubstituted fluoroalkenes, is also reported. Finally, the use of a three-step synthesis sequence, including Mizoroki-Heck reaction, allows the synthesis of fluorinated analogs of therapeutic agents with high yield.

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