Category: naphthyridine

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: 91523-50-1, is researched, SMILESS is OC(=O)C1NCCC2=C1C=CC(O)=C2, Molecular C10H11NO3Conference, Applied Biocatalysis called Chemo-enzymatic synthesis of (S)-1,2,3,4-tetrahydroisoquinoline carboxylic acids using D-amino acid oxidase, Author is Ju, Shuyun; Qian, Mingxin; Xu, Gang; Yang, Lirong; Wu, Jianping, the main research direction is tetrahydroisoquinoline carboxylic acid FsDAAO catalyst enantioselective enzymic resolution; chiral tetrahydroisoquinoline carboxylic acid preparation.HPLC of Formula: 91523-50-1.

In this context, an (R)-selective D-amino acid oxidase from Fusarium solani M-0718 (FsDAAO) with broad substrate scope and excellent enantioselectivity was found through genome mining. This enzyme was applied for the kinetic resolution of a range of racemic 1- and 3-carboxyl substituted THIQs with different substitutions on the aryl rings. Preparative-scale deracemization of racemic 1,2,3,4- tetrahydroisoquinoline-1-carboxylic acid and 1,2,3,4-tetrahydroisoquinoline-3- carboxylic acid was further demonstrated.

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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 Novel Allosteric Ligands of γ-Aminobutyric Acid Transporter 1 (GAT1) by MS Based Screening of Pseudostatic Hydrazone Libraries, published in 2018-11-21, which mentions a compound: 2689-65-8, mainly applied to nipecotic acid pseudostatic hydrazone library preparation GAT1 allosteric ligand, Recommanded Product: 2689-65-8.

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

Popiolek, Lukasz; Biernasiuk, Anna; Paruch, Kinga; Malm, Anna; Wujec, Monika published an article about the compound: 5-Iodo-2-furaldehyde( cas:2689-65-8,SMILESS:IC1=CC=C(O1)C=O ).Application In Synthesis of 5-Iodo-2-furaldehyde. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:2689-65-8) through the article.

Thirteen new 3-acetyl-2,5-disubstituted-1,3,4-oxadiazoline derivatives were synthesized from corresponding hydrazide-hydrazones of isonicotinic acid in the reaction with acetic anhydride. The obtained compounds were identified with the use of spectral methods (IR, 1H-NMR, 13C-NMR, MS). In vitro antimicrobial activity screening of synthesized compounds against a panel of bacteria and fungi revealed interesting antibacterial and antifungal activity of tested 1,3,4-oxadiazoline derivatives, which is comparable to that of commonly used antimicrobial agents.

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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 Syntheses of naphthyridine derivatives. IV. Syntheses of 1,8-naphthyridines and their hydrogenation, published in 1942, which mentions a compound: 1569-17-1, mainly applied to , HPLC of Formula: 1569-17-1.

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

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).HPLC of Formula: 1569-17-1. 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

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, Issled. Termogr. Korroz. called Thermographic study of the reaction of primary aryl amines with 5-halofurfurals, Author is Tovmas’yan, I. K.; Lyutkin, N. I.; Myasnikova, T. P., which mentions a compound: 2689-65-8, SMILESS is IC1=CC=C(O1)C=O, Molecular C5H3IO2, SDS of cas: 2689-65-8.

Thermograms of the reaction of 5-halofurfural with primary aryl amines were studied. The 1st macrostage corresponded to the formation of 5-halofurfurylidenearyl amines, the 2nd stage to N-[5-arylaminofurfurylidene]arylamine. Effect of substitutes in amine and aldehyde components on the 1st and the 2nd reaction stages was comparatively analyzed from the thermogram data.

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

SDS of cas: 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 An unusual photochemical reaction of indene with furan and thiophene derivatives. Author is D’Auria, Maurizio; De Mico, Antonella; D’Onofrio, Franco.

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 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 A simple preparative synthesis of epoxy[1,3]oxazino(or oxazolo)[2,3-a]isoindoles and their thia analogues via IMDAF, published in 2010-09-01, which mentions a compound: 2689-65-8, Name is 5-Iodo-2-furaldehyde, Molecular C5H3IO2, COA of Formula: C5H3IO2.

Azomethines, easily prepared from 5-(R)-furfurals and 1,3- or 1,2-amino alcs. (aminothiols), react under mild conditions with maleic anhydride affording 8,10a-epoxy[1,3]oxa(thia)zino[2,3-a]isoindole-7- and 7,9a-epoxy[1,3]oxa(thia)zolo[2,3-a]isoindole-6-carboxylic acids. The reaction proceeds through initial N-acylation with subsequent intramol. exo-Diels-Alder cycloaddition and stereoselectively leads to the exo adducts. The ‘one-pot’ synthetic protocol is also presented.

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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.COA of Formula: C5H3IO2. The article 《3-(5-X-2-Furyl)-2-cyanoacrylonitriles on reaction with 2-cyanomethylbenzothiazole》 in relation to this compound, is published in Collection of Czechoslovak Chemical Communications. Let’s take a look at the latest research on this compound (cas: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

Ostapko, Jakub; Kelm, Anna; Kijak, Michal; Lesniewska, Barbara; Waluk, Jacek published the article 《Two Macrocycles in One Shot: Synthesis, Spectroscopy, Photophysics, and Tautomerism of 23-Oxahemiporphycene and 21-Oxacorrole-5-carbaldehyde》. Keywords: oxahemiporphycene preparation IR NMR photophys tautomerism; oxacorrolecarboxaldehyde preparation IR NMR photophys tautomerism; corroles; porphyrinoids; reaction mechanisms; structure elucidation; tautomerism.They researched the compound: 5-Iodo-2-furaldehyde( cas:2689-65-8 ).COA of Formula: C5H3IO2. 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 synthesis of 23-oxahemiporphycene, the first monooxa analog of hemiporphycene, a structural isomer of porphyrin, is reported. Its generation under McMurry reaction conditions is surprisingly accompanied by the appearance of a formyl derivative of oxacorrole, 21-oxacorrole-5-carbaldehyde. A mechanism for the formation of the latter is proposed, relying on pinacol rearrangement of titanium pinacolate. The structures of the most stable tautomeric forms are established for both compounds based on IR and NMR spectra combined with DFT calculations Spectral and photophys. characteristics are compared with those of structurally similar macrocycles. Replacement of one nitrogen by oxygen in hemiporphycene has only a minor impact. In contrast, for corrole it leads to the enhancement of stability and to strongly reduced rates of nonradiative deactivation of the lowest excited singlet state. This is explained by the planarity of oxacorroles, achieved by removing one of the inner hydrogen atoms from the inner cavity. Unusual crystal packing is observed for the protonated form of 23-oxahemiporphycene, which exhibits a π-π stacked columnar alignment of pos. charged macrocycle units.

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