Month: April 2022

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: 847818-64-8, is researched, Molecular C7H13BN2O2, about A versatile method for Suzuki cross-coupling reactions of nitrogen heterocycles, the main research direction is heteroaryl halide heteroarylboronic acid Suzuki cross coupling palladium; heteroarylboronic acid aryl halide Suzuki cross coupling palladium; nitrogen heterocycle preparation; pyridine aryl derivative preparation; palladium Suzuki cross coupling catalyst.Reference of (1-Isobutyl-1H-pyrazol-5-yl)boronic acid.

A wide-ranging study of Suzuki reactions which use nitrogen-containing heterocycles was described. This method was highly versatile (a single procedure was used for all substrates, including boronate esters and trifluoroborates), compatible with a variety of unprotected functionalities (e.g., NH2- and OH-substituted substrates), and efficient even with inactivated aryl chlorides.

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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 《Naphthyridine chemistry. V. One-step synthesis of 1,8-naphthyridines》. Authors are Paudler, William W.; Kress, Thomas J..The article about the compound:4-Methyl-1,8-naphthyridinecas:1569-17-1,SMILESS:CC1=C2C=CC=NC2=NC=C1).Recommanded Product: 4-Methyl-1,8-naphthyridine. Through the article, more information about this compound (cas:1569-17-1) is conveyed.

cf. CA 66, 6881q; 65, 16955a; 64, 5057c. 2-Aminopyridine treated with Utermohlen’s “”sulfo-mix”” (CA 38, 9735) and glycerol gave 30% 1,8-naphthyridine. Similarly were prepared 2-methyl-, 4-methyl-, and 2,4-dimethyl-1,8-naphthyridines (I,II, and III). N.M.R. spectra data are given for the compounds

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Reference:
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: 4-Methyl-1,8-naphthyridine( cas:1569-17-1 ) is researched.SDS of cas: 1569-17-1.Jones, Richard A. Y.; Wagstaff, Nigel published the article 《Kinetics of quaternization of some naphthyridines and methylnaphthyridines》 about this compound( cas:1569-17-1 ) in Chemical Communications (London). Keywords: quaternization kinetics heterocycle; kinetics quaternization heterocycle; heterocycle quaternization kinetics; naphthyridines quaternization kinetics; quinoline quaternization kinetics; isoquinoline quaternization kinetics. Let’s learn more about this compound (cas: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

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

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 Polar properties and reactivities of some 5-substituted furfurals, the main research direction is dipole moment furfurals; furfurals dipole moment; Hammett constant furfurals; reaction rates furfurals; rates reaction furfurals.Synthetic Route of C5H3IO2.

The dipole moments (μ) were determined of the following 5-substituted furfurals (I) (substituent and μ given): Et2N, 5.66; Me2N, 5.50; piperidino, 5.43; PhNMe, 4.95; morpholino, 4.81; Me, 3.94; CHO, 3.46; H, 3.57; Br, 3.37; Cl, 3.37; I, 3.29. Linear correlations were obtained between μ and Hammett σ constant of the substituents. The relative reaction rates (k) were also determined for the reactions of I with PhNH2. A linear plot was obtained when μ were plotted vs. log k. I (R = Me, NMe2, or NEt2) have in solution primarily the cis configuration.

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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 Chemoenzymatic Approach to (S)-1,2,3,4-Tetrahydroisoquinoline Carboxylic Acids Employing D-Amino Acid Oxidase, published in 2019, which mentions a compound: 91523-50-1, Name is 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid, Molecular C10H11NO3, Safety of 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid.

Optically pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids constitute an important class of building blocks for the synthesis of natural products and synthetic pharmaceuticals. However, redox deracemization of racemic 1,2,3,4-tetrahydroisoquinoline carboxylic acids as an attractive method is still challenging for the lack of suitable oxidoreductases. Herein, a D-amino acid oxidase from Fusarium solani M-0718 (FsDAAO) with broad substrate scope and excellent enantioselectivity was exploited through genome mining, and applied for the kinetic resolution of a number of racemic 1- and 3-carboxyl substituted tetrahydroisoquinolines to yield the corresponding (S)-enantiomers with excellent enantiomeric excess (ee) values (up to >99%). By using FsDAAO in combination with ammonia-borane in one pot, deracemization of these racemic carboxyl-substituted tetrahydroisoquinolines was achieved with conversions up to >98% and >99% ee. Preparative-scale deracemization of racemic 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid and 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid was also demonstrated with good isolated yields (82% and 73%, resp.) and ee>99%. Our study provides an effective method for the synthesis of enantiomeric pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids. This method is expected to provide access to chiral carboxyl-substituted 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydro-ss-carbolines.

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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 Preparation and properties of 3,5-disubstituted rhodanines, the main research direction is rhodanine benzylfurfurylidene; benzylrhodanine furfurylidene; furfurylidenerhodanine benzyl.SDS of cas: 2689-65-8.

3-Benzyl-5-furfurylidenerhodanines I (R = H, Cl, Br, I) were prepared by condensation of 3-benzylrhodanine (II) with furfural or its 5-halo derivatives in AcOH-AcONa. II was prepared by treatment of PhCH2NH2 with CS2 and KOH, condensation of the resulting PhCH2NHCS2K with ClCH2CO2K, and cyclization in the presence of concentrated HCl.

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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 Iterative Arylation of Amino Acids and Aliphatic Amines via δ-C(sp3)-H Activation: Experimental and Computational Exploration, published in 2019, which mentions a compound: 2689-65-8, mainly applied to arylalkyl amine preparation; aliphatic amine aryl iodide arylation palladium catalyst; amino acid derivative aryl iodide arylation palladium catalyst; BODIPY labeling; arylation; density functional calculations; mechanistic studies; natural products, Reference of 5-Iodo-2-furaldehyde.

Directed C-H functionalization has been realized as a complementary tool to the traditional approaches for a straightforward access of non-proteinogenic amino acids; albeit such a process is restricted mostly up to the γ-position. In the present work, we demonstrate the diverse (hetero)arylation of amino acids and analogous aliphatic amines selectively at the remote δ-position by tuning the reactivity controlled by ligands. An organopalladium δ-C(sp3)-H activated intermediate has been isolated and crystallog. characterized. Mechanistic investigations carried out exptl. in conjunction with computational studies shed light on the difference in the mechanistic picture depending on the substrate structure.

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

Synthetic Route 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 Solvent effect on rotational isomerism of furfural and its 5-substituted derivatives. Author is Rodgriguez, M.; Fernandez Bertran, J..

The solvent effect on the rotamer distribution of I (R = H) was determined from the 5Jα,4 and the 6Jα,5 in the PMR; 5Jn was inversely proportional to 6J. Polar solvents favored the cis-OO population. The substituent effect on the equilibrium was determined from the 5J for I (R = NO2, Cl, Br, I, Me2N); electron donating substituents also favored the cis-OO rotamer.

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

Safety of 4-Methyl-1,8-naphthyridine. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 4-Methyl-1,8-naphthyridine, is researched, Molecular C9H8N2, CAS is 1569-17-1, about Kinetics of quaternization of some naphthyridines and methylnaphthyridines. Author is Jones, Richard A. Y.; Wagstaff, Nigel.

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