Month: March 2022

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《The hydrogen bonding energies from near-ultraviolet absorption spectra in p-bromophenol and o-hydroxybiphenyl》. Authors are Devanathan, T..The article about the compound:5-Iodo-2-furaldehydecas:2689-65-8,SMILESS:IC1=CC=C(O1)C=O).SDS of cas: 2689-65-8. Through the article, more information about this compound (cas:2689-65-8) is conveyed.

K, ΔG, and ΔH were estimated for the systems: (I) p-bromophenol (0.07994M) and EtOAc (0.4033M), and (II) o-hydroxybiphenyl (0.1212M) and EtOAc (0.3231M), with n-heptane as the solvent. For I, at 35 and 55°, resp., λ = 284 mμ, K = 29.16 and 20.09, ΔG = -2.07 and -1.96 kcal./mole, and ΔH = -3.90 kcal./mole. For II, at 45, 55, and 65°, resp., λ = 284mμ, K = 2.98, 2.06, and 1.36, ΔG = -0.69, -0.47, and -0.21 kcal./mole, and ΔH = -0.84 kcal./mole. The calculated ΔH value of II is too low, which indicates an intramol. H bond.

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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 1,8-Naphthyridines. I. Derivatives of 2- and 4-methyl-1,8-naphthyridines, published in 1965, which mentions a compound: 1569-17-1, Name is 4-Methyl-1,8-naphthyridine, Molecular C9H8N2, Related Products of 1569-17-1.

2-Methyl-1,8-naphthyridine has been prepared by a series of reactions starting with 2-methyl-5-hydroxy-1,8-naphthyridine-6-carboxylic acid and compared with the known 4-methyl-1,8-naphthyridine. The compound previously thought to be 2-methyl-4-hydroxy-7-amino-l,8-naphthyridine has been shown to be 2-hydroxy-4-methyl-7-amino-1,8-naphthyridine by conversion to 4-methyl-1,8-naphthyridine. A new ring closure has furnished 2-methyl-7-amino-1,8-naphthyridine and, in addition, 2-amino-5-methyl-1,8-naphthyridine and 2-methyl-5-amino-1,8-naphthyridine have been prepared by other means.

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

HPLC of Formula: 2689-65-8. 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 Metallic salt-catalyzed direct indium insertion into alkyl iodides and their applications in cross-coupling reactions. Author is Chen, Bing-Zhi; Wang, Chuang-Xin; Jing, Zhen-Hua; Chu, Xue-Qiang; Loh, Teck-Peng; Shen, Zhi-Liang.

An efficient method for the synthesis of alkyl indium reagents by an indium(III) or lead(II) halide-catalyzed direct insertion of indium into alkyl iodides and their applications in palladium-catalyzed cross-coupling reactions with aryl halides is developed. NMR and ESI-MS analyses indicated that rather than the formation of the commonly recognized alkyl indium sesquihalide with the formulation of R3In2X3, the formed alkyl indium reagent in the present protocol should be a mixture of an alkyl indium dihalide (RInX2) and a dialkyl indium halide (R2InX) (both of them presumably exist as dimers).

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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).Category: naphthyridine. 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

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2-Bromo-1-(1-methyl-1H-pyrrol-2-yl)ethanone, is researched, Molecular C7H8BrNO, CAS is 65438-97-3, about 4-Acetylamino-3-(imidazol-1-yl)-benzoic acids as novel inhibitors of influenza sialidase, the main research direction is acetylaminoimidazolylbenzoic acid preparation influenza sialidase inhibitor; imidazolylbenzoic acid preparation influenza sialidase inhibitor; benzoic acid imidazolyl preparation influenza sialidase inhibitor; virucide anti viral agent acetylaminoimidazolylbenzoic acid.Category: naphthyridine.

Two methods for the synthesis of 4-acetylaminobenzoic acids substituted at the 3-position with imidazoles are described. Thus, 4-acetylamino-3-aminobenzoic acid tert-Bu ester was N-alkylated with RCH2COBr (R = Ph, Et, benzofuran-3-yl, etc.) followed by cyclization with cyanamide and hydrolysis to give imidazolylbenzoic acids I (R1 = Ph, furyl, Et, etc.; R2 = NH2). Imidazolylbenzoic acids I (R1 = H; R2 = NH2, H, Et) were prepared by addition of the appropriate imidazole to 3-fluoro-4-nitrobenzoic acid tert-Bu ester followed by reduction of the nitro group, acetylation, and hydrolysis. Many of the compounds are inhibitors of influenza virus sialidases with levels of activity similar to the recently described 4-acetylamino-3-guanidino-benzoic acid (BANA 113).

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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 General synthetic approach towards annelated 3a,6-epoxyisoindoles by tandem acylation/IMDAF reaction of furylazaheterocycles. Scope and limitations.Recommanded Product: 2689-65-8.

An efficient and versatile one-pot synthesis of 3,6a-epoxyisoindoles annelated with oxazine, oxazole, thiazine, thiazole, pyrimidine fragments and with their benzoannelated analogs is presented. The method is based on tandem N-acylation/intramol. cycloaddition (the intramol. Diels-Alder reaction of furan, IMDAF) reaction between α,β-unsaturated acid anhydrides and α-furyl substituted azaheterocycles. The latter can be easily prepared by condensation of diverse furfurals and 1,2- or 1,3-N,X-binucleophiles (aminoalcs., aminothiols, diamines). The observed IMDAF reaction is stereoselective: exo-adducts are formed exclusively with large prevalence of one of the diastereoisomers. In most cases, the condensation/N-acylation/IMDAF reaction sequence may be carried out via a one-pot domino protocol. The scope and limitations of the proposed approach are thoroughly investigated. The obtained Diels-Alder adducts are attractive and useful substrates for further transformations. Fused isoindoles can be prepared from them in one-step by aromatization of the 7-oxabicyclo[2.2.1]heptene ring. Other transformations, including halogenation, ring cleavage, and Wagner-Meerwein skeletal rearrangement, are also demonstrated. The spatial structures of the obtained compounds have been established by X-ray diffraction analyses.

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

Application of 2689-65-8. 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 Mechanism and kinetics of furfural oxidation by hydrogen peroxide. Author is Badovskaya, L. A.; Kul’nevich, V. G.; Muzychenko, G. F.; Kaklyugina, T. Ya..

The 1st-order rate constants and activation parameters for oxidation of furfural by H2O2 and the effect of 5-substituents on the rate constant indicated a heterolytic mechanism with loss of rotational and translational degrees of freedom in the transition state.

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

Application of 2689-65-8. 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: 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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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: 5-Iodo-2-furaldehyde( cas:2689-65-8 ) is researched.Name: 5-Iodo-2-furaldehyde.Hoyle, William; Roberts, Gordon P.; Meth-Cohn, Otto published the article 《Potential antimicrobial furans》 about this compound( cas:2689-65-8 ) in Journal of Medicinal Chemistry. Keywords: furan antibacterial. Let’s learn more about this compound (cas:2689-65-8).

Furan derivatives bearing isosteric and isoelec. functional groups in place of a 2-nitro group lacked antibacterial activity, confirming the essential role of the nitro group in activity. Functional groups employed were sulfo, sulfamoyl, carboxyl, methoxycarbonyl, carbamoyl, and cyano. For example, 5-iodo-2-furaldehyde [2689-65-8] reacted with Cu2(CN)2 in DMF to form 5-formyl-2-furonitrile [42061-89-2], which was condensed with semicarbazide [57-56-7], 3-amino-2-oxazolidinone, or 1-aminohydantoin to yield 5-cyano-2-furancarboxaldehyde semicarbazone [42061-90-5], 3-[[(5-cyano-2-furanyl)methylene]amino]-2-oxazolidinone [42978-22-3], and 1-[[(5-cyano-2-furanyl)methylene]amino]-2,4-imidazolidinedione (I) [42061-92-7], resp.

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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: 2689-65-8, is researched, SMILESS is IC1=CC=C(O1)C=O, Molecular C5H3IO2Journal, Journal of Heterocyclic Chemistry called [4+2] Cycloaddition of α,β-unsaturated acid anhydrides to 2-furylpiperidin-4-ones: The short route to annulated 8,10a-epoxypyrido[2,1-a]isoindoles, Author is Zubkov, Fedor I.; Airiyan, Inga K.; Dzyubenko, Anastasiya A.; Yudina, Nataliya I.; Zaytsev, Vladimir P.; Nikitina, Eugeniya V.; Varlamov, Alexey V.; Khrustalev, Victor N.; Grudinin, Dmitry G., the main research direction is regioselective stereoselective preparation epoxypyridoisoindole; intramol Diels Alder reaction furfurylacrylamide unsaturated anhydride.HPLC of Formula: 2689-65-8.

A one-step preparation procedure of 8,10a-epoxypyrido[2,1-a]isoindoles and their 7-carboxylic derivatives is reported. The key synthetic step includes the intramol. exo-Diels-Alder reaction (IMDAF) of N-furfurylacrylamide, produced in situ from 2-furylpiperidin-4-ones and α,β-unsaturated acid anhydrides. The synthesis of the title compounds can be performed under mild conditions with a high level of regio- and stereoselectivity. The same strategy has been successfully used for the synthesis of 9,11a-epoxyimidazo[4′,5′:3,4]pyrido[2,1-a]isoindole-8-carboxylic acid from maleic anhydride and the spinacine derivatives – 4-(2-furyl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridines.

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