Month: April 2022

Electric Literature of C5H3IO2. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about Uracil-Directed Ligand Tethering: An Efficient Strategy for Uracil DNA Glycosylase (UNG) Inhibitor Development. Author is Jiang, Yu Lin; Krosky, Daniel J.; Seiple, Lauren; Stivers, James T..

Uracil DNA glycosylase (UNG) is an important DNA repair enzyme that recognizes and excises uracil bases in DNA using an extrahelical recognition mechanism. It is emerging as a desirable target for small-mol. inhibitors given its key role in a wide range of biol. processes including the generation of antibody diversity, DNA replication in a number of viruses, and the formation of DNA strand breaks during anticancer drug therapy. To accelerate the discovery of inhibitors of UNG we have developed a uracil-directed ligand tethering strategy. In this efficient approach, a uracil aldehyde ligand is tethered via alkyloxyamine linker chem. to a diverse array of aldehyde binding elements. Thus, the mechanism of extrahelical recognition of the uracil ligand is exploited to target the UNG active site, and alkyloxyamine linker tethering is used to randomly explore peripheral binding pockets. Since no compound purification is required, this approach rapidly identified the first small-mol. inhibitors of human UNG with micromolar to submicromolar binding affinities. In a surprising result, these uracil-based ligands are found not only to bind to the active site but also to bind to a second uncompetitive site. The weaker uncompetitive site suggests the existence of a transient binding site for uracil during the multistep extrahelical recognition mechanism. This very general inhibitor design strategy can be easily adapted to target other enzymes that recognize nucleobases, including other DNA repair enzymes that recognize other types of extrahelical DNA bases.

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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: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about [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, the main research direction is regioselective stereoselective preparation epoxypyridoisoindole; intramol Diels Alder reaction furfurylacrylamide unsaturated anhydride.Quality Control of 5-Iodo-2-furaldehyde.

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

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).Related Products 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

Product Details of 2689-65-8. 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 Palladium-Catalyzed Cross-Coupling of Indium Homoenolate with Aryl Halide with Wide Functional Group Compatibility. Author is Shen, Zhi-Liang; Lai, Yin-Chang; Wong, Colin Hong An; Goh, Kelvin Kau Kiat; Yang, Yong-Sheng; Cheong, Hao-Lun; Loh, Teck-Peng.

An efficient palladium-catalyzed cross-coupling of indium homoenolate with aryl halide is described. The reactions proceeded efficiently in DMA at 100 °C to afford the desired products of β-aryl ketones in moderate to good yields. Various important functional groups including ketone, ester, aldehyde, nitrile, hydroxide, and nitro groups can be well tolerated in the protocol.

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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, Chemicke Zvesti called Furan derivatives. LXXX. Synthesis and properties of substituted furfurylideneoxindoles, Author is Kovac, J.; Stetinova, J., which mentions a compound: 2689-65-8, SMILESS is IC1=CC=C(O1)C=O, Molecular C5H3IO2, COA of Formula: C5H3IO2.

Oxindoles I (R1 = R2 = H, R = H, NO2, Cl, Br, I, Me, MeS, CO2Me, p- and m-O2NC6H4, Me2N; R1 = H, R2 = NO2, R = H, Cl, Br, I, Me, MeS, Ac, 4-O2NC6H4; R1 = Ac, R2 = H, R = H, NO2, Cl, Br, I, Me, MeS, NMe2) were prepared by condensation of oxindole, 5-nitrooxindole, and 1-acetyloxindole, resp., with the resp. furancarboxyaldehydes, some I (R1 = Ac) were prepared by acetylation of I (R1 = H). UV, IR and mass spectra of I were interpreted.

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

Electric Literature of C5H3IO2. 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 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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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

HPLC of Formula: 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 Preparation of Aryl and heteroaryl indium(III) reagents by the direct insertion of indium in the presence of LiCl. Author is Chen, Yi-Hung; Knochel, Paul.

Sensitive functional groups, including ketone, aldehyde, and ester groups, may be present in aryl In reagents prepared in good to excellent yields by the treatment of aryl and heteroaryl iodides with In powder in the presence of LiCl. These functionalized organoindium(III) reagents readily undergo Pd-catalyzed cross-coupling with functionalized aryl iodides, including those containing NH or OH groups.

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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: 5-Iodo-2-furaldehyde(SMILESS: IC1=CC=C(O1)C=O,cas:2689-65-8) is researched.Application In Synthesis of 5-Iodo-2-furaldehyde. The article 《Determination of NH2 concentration on 3-aminopropyl tri-ethoxy silane layers and cyclopropylamine plasma polymers by liquid-phase derivatization with 5-iodo 2-furaldehyde》 in relation to this compound, is published in Applied Surface Science. Let’s take a look at the latest research on this compound (cas:2689-65-8).

The quantification of concentration of primary amines, e.g. in plasma polymerized layers, is a very important task for surface anal. However, the commonly used procedure, such as gas phase derivatization with benzaldehydes, shows several drawbacks, the most important of which are the side reaction effects. The authors propose and validate a liquid phase derivatization using 5-iodo 2-furaldehyde (IFA). The content of NH2 groups can be determined from the at. concentrations measured by XPS, in particular from the ratio of I 3d and N 1s peak intensities. First, the authors demonstrate the method on a prototypical system such as 3-aminopropyl tri-ethoxy silane (APTES) layer. Here the XPS anal. carried out after reaction of APTES layer with IFA gives the fraction of primary amines (NH2/N) of 38.3 ± 7.9%. Comparing this value with that obtained by N 1s curve fitting of APTES layer giving 40.9 ± 9.5% of amine groups, all primary amines were derivatized by reaction with IFA. The second system to demonstrate the method comprises cyclopropylamine (CPA) plasma polymers that were free from conjugated imines. In this case the method gives the NH2 fraction ∼8.5%. This value is closely matching the NH2/N ratio estimated by 4-trifluoromethyl benzaldehyde (TFBA) derivatization. The reaction of IFA with CPA plasma polymer exhibiting high d. of conjugated imines revealed the NH2/N fraction of ∼10.8%. This value was significantly lower compared to 17.3% estimated by TFBA derivatization. As the overestimated d. of primary amines measured by TFBA derivatization is probably related to the side reaction of benzaldehydes with conjugated imines, the proposed IFA derivatization of primary amines can be an alternative procedure for the quantification of surface amine groups.

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

Application In Synthesis of 5-Iodo-2-furaldehyde. 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 [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..

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

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: 16710-11-5, is researched, Molecular C6H8N2OS, about Thiouracils. 2. Tautomerism and infrared spectra of thiouracils. Matrix-isolation and ab initio studies, the main research direction is thiouracil tautomer IR; methylthiouracil isomer IR; MO ab initio thiouracil.Reference of 4-Methyl-6-(methylthio)pyrimidin-2-ol.

A study of the IR spectra of thiouracils isolated in low-temperature inert matrixes demonstrated that 2- and 4-thiouracils together with their N1- and N3-methylated derivatives as well as 2,4-dithiouracil exist under these conditions only in the oxothione or dithione tautomeric forms. In contrast, S2- and S4-methylated derivatives exist as a mixture of hydroxy and oxo tautomeric forms under the same conditions. The ratio of concentrations of the oxo and hydroxy tautomers and the free energy differences, were exptl. estimated, from the ratio of the absorbances of the NH and OH stretches. An assignment of the observed IR bands, particularly those related to the C:S stretching vibrations, is proposed on the basis of the comparison of the matrix spectra with those calculated by using ab initio methods (3-21G* basis set).

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