Month: April 2022

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis and study of N-oxides of heterocyclic compounds. I. N-Oxides of derivatives of morphine, tetra-hydroisoquinoline, and quinoline》. Authors are Khaletskii, A. M.; Pesin, V. G.; Tsin, Chshou.The article about the compound:8-Hydroxyquinoline 1-oxidecas:1127-45-3,SMILESS:OC1=CC=CC2=CC=C[N+]([O-])=C12).SDS of cas: 1127-45-3. Through the article, more information about this compound (cas:1127-45-3) is conveyed.

cf. Ochiai, C.A. 48, 3359i. Heating 8.4 g. codeine with 45 ml. 3% H2O2 at 50-60° gave after evaporation 8 g. codeine N-oxide, m. 206-8° (H2O); HCl salt, m. 214-17° (EtOH). To 5 g. dihydrohydroxycodeinone-HCl was added 10 ml. 10% NaOH yielding 93% dihydrohydroxycodeinone, m. 213-16°, which with 3% H2O2 as above gave 46.2% dihydrohydroxycodeinone N-oxide, decompose 152-3°, which gives a red color with Ac2O; picrate, m. 190-2°; HCl salt, m. 167-8°. The oxide treated with SO2 in warm EtOH gave 62.5% C18H23O8NS, decompose 169-70°, which was evidently an isomer of dihydrohydroxycodeinone sulfate; with BaCl2 solution it readily gave BaSO4; hydrolysis with 10% NaOH gave the original dihydrohydroxycodeinone, m. 207-9° (sulfate, m. 138-9°). Salsolidine (3 g.) in 20 ml. Me2CO and 30 ml. H2O treated with 2.5 ml. 30% H2O2 after several days at room temperature gave 15.48% N-hydroxysalsolidine, m. 100-1° (aqueous EtOH), which reduced Fehling and Tollens reagents. Similarly, N-methylsalsolidine gave N-methylsalsolidine N-oxide picrate, m. 133-4° (aqueous EtOH); HCl salt analog, decompose 162-3°. Oxidation of salsoline with 3% H2O2 in AcOH or with BzO2H in CHCl3 either gave no reaction or failed to yield any definite products. N-Methylsalsoline with aqueous H2O2 at room temperature in 3 days gave N-methylsalsoline N-oxide, m. 183° (EtOH); HCl salt, m. 186°. Oxidation of 8-hydroxyquinoline in CHCl3 with BzO2H with cooling gave yellow 8-hydroxyquinoline N-oxide, m. 137-8° (H2O); the same formed on oxidation with 30% H2O2 in AcOH-Ac2O at 40-5° in 3 hrs., but with 30% H2O2-AcOH in 2 hrs. only the starting material was recovered. 8-Hydroxyquinoline N-oxide treated with alc. KOH and Etl at reflux gave 8-ethoxyquinoline N-oxide, isolated as picrate, m. 135-8°; the same formed on treatment of 8-ethoxyquinoline with AcOH-Ac2O-30% H2O2 at 45-50°; HCl salt, m. 158°; free oxide, m. 61-2°. Similarly 2-phenylquinoline-4-carboxylic acid and AcOH-H2O2 gave 76% N-oxide, m. 244°, and 15% benzoylanthranilic acid, m. 170-2°. Oxidation of 2-phenylquinoline-4-carboxylic acid with BzO2H in CHCl3 in 2 days gave no evident reaction, the same being true of oxidation with 25% H2O2 in EtOH-Me2CO at 50°. Reduction of 2-phenylquinoline-4-carboxylic acid N-oxide with Na hydrosulfite in aqueous EtOH gave the original 2-phenylquinoline-4-carboxylic acid, m. 205-7°.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Electric Literature of C38H34N2O4P2. 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: (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine, is researched, Molecular C38H34N2O4P2, CAS is 221012-82-4, about Rhodium-Catalyzed Asymmetric [2+2+2] Cycloaddition of 1,6-Enynes with Racemic Secondary Allylic Alcohols through Kinetic Resolution. Author is Suzuki, Shunsuke; Shibata, Yu; Tanaka, Ken.

It has been established that a cationic rhodium(I)/P-phos complex catalyzes the asym. [2+2+2] cycloaddition of 1,6-enynes R1CCCH2ZCH2CH(=CH2)R2 (R1 = Me, Ph, pentyl; R2 = H, Me) with racemic secondary allylic alcs. R3CH(OH)CH=CH2 to produce the corresponding chiral bicyclic cyclohexenes I, possessing three stereogenic centers, as a single diastereomer with excellent ee values. Mechanistic experiments revealed that the present cycloaddition proceeds through the kinetic resolution of the racemic secondary allylic alcs., in which one enantiomer preferentially reacts with the 1,6-enyne.

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

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: 13940-83-5, is researched, SMILESS is [H]O[H].[H]O[H].[H]O[H].[H]O[H].[Ni+2].[F-].[F-], Molecular F2H8NiO4Journal, Chimia called Photoelectron spectrometry of inorganic solid, Author is Joergensen, Christian K., the main research direction is photoelectron spectrometry inorganic solid; Hartree potentials photoelectron spectrometry; Madelung potential ionic compound.Reference of Nickel(ii)fluoridetetrahydrate.

A discussion ia given of the highly different probability of ionization of each shell of a given element by x-ray photons. The chem. shift of ionization energies I indicate differing Hartree potentials. The multiple I of an inner shell in systems having pos. spin quantum number S were studied in 11 high-spin Ni(II) compounds Scotch tape was used as internal standard The Madelung potential in almost ionic compounds and the relation between optical electronegativities and I of valence electrons are treated.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

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 8-Hydroxy-1-methoxyquinoline methosulfate, published in 1965, which mentions a compound: 1127-45-3, Name is 8-Hydroxyquinoline 1-oxide, Molecular C9H7NO2, Reference of 8-Hydroxyquinoline 1-oxide.

The crude title compound, not described previously, m. 126-8° (decomposition) and is very soluble in water, soluble in alcs., and insoluble in nonpolar solvents. Reaction with nucleophilic compounds gives 2-substituted 8-hydroxyquinolines. A mixture of 48.3 g. powd. 8-hydroxyquinoline 1-oxide (m. 138.5-39°) (Phillips, et al., CA 51, 11349a; Murase and Demura, CA 58 3390b, recrystallized twice from water and C6H6) and 37.9 g. freshly distilled Me2SO4 is warmed on a water bath 2 hrs. with reflux. The mass is cooled and stirred until crystallization, 200 ml. dry Et2O is added, and the mixture stirred until all material is hardened. The solid is washed with 50-100 ml. Et2O in a mortar after filtration, washed on the filter with Et2O, and dried in a vacuum desiccator. Yield 77.6-9.3 g. hygroscopic material. Recrystallization of 20 g. from EtOH-Et2O gave 3.67 g., m. 143-4.5°.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

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: 19777-66-3, is researched, SMILESS is C[C@H](N)CN.[H]Cl.[H]Cl, Molecular C3H12Cl2N2Journal, Article, Chemistry – A European Journal called π-π Stacking interaction in an oxidized CuII-Salen complex with a side-chain indole ring: An approach to the function of the tryptophan in the active site of galactose oxidase, Author is Oshita, Hiromi; Suzuki, Takashi; Kawashima, Kyohei; Abe, Hitoshi; Tani, Fumito; Mori, Seiji; Yajima, Tatsuo; Shimazaki, Yuichi, the main research direction is galactose oxidase active site mimic copper salen complex tryptophan; copper; heterocycles; oxidation; pi interactions; radicals.Formula: C3H12Cl2N2.

In order to gain new insights into the effect of the π-π stacking interaction of the indole ring with the CuII-phenoxyl radical as seen in the active form of galactose oxidase, we have prepared a CuII complex of a methoxy-substituted salen-type ligand, containing a pendent indole ring on the dinitrogen chelate backbone, and characterized its one-electron-oxidized forms. The X-ray crystal structures of the oxidized CuII complex exhibited the π-π stacking interaction of the indole ring mainly with one of the two phenolate moieties. The phenolate moiety in close contact with the indole moiety showed the characteristic phenoxyl radical structural features, indicating that the indole ring favors the π-π stacking interaction with the phenoxyl radical. The UV/Vis/NIR spectra of the oxidized CuII complex with the pendent indole ring was significantly different from those of the complex without the side-chain indole ring, and the absorption and CD spectra exhibited a solvent dependence, which is in line with the phenoxyl radical-indole stacking interaction in solution The other physicochem. results and theor. calculations strongly support that the indole ring, as an electron donor, stabilizes the phenoxyl radical by the π-π stacking interaction.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

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: 32717-95-6, is researched, Molecular C16H16Cl2Cu2, about Asymmetric [4 + 3] Annulations for Constructing Divergent Oxepane Frameworks via Cooperative Tertiary Amine/Transition Metal Catalysis, the main research direction is oxepane framework preparation enantioselective diastereoselective; indole vinyl carbonate amine metal catalyst annulation.Recommanded Product: 32717-95-6.

Asym. [4+3] annulations between isatin-derived Morita-Baylis-Hillman carbonates and two types of vinyl carbonates synergistically catalyzed by tertiary amines and transition metals, through chemoselective assemblies of in situ formed allylic ylides and metal-containing 1,4-dipoles were reported. A range of oxepane frameworks I [R1 = H, 5-Me, 5-Br, etc.; R2 = Me, Et; R3 = Me, allyl, Bn, etc.] and II [X = CF, CCH3, NH, etc.] were generally constructed in moderate to good yields with high stereocontrol. Moreover, all four diastereomers for the products bearing vicinal stereocenters were accessible by tuning tertiary amine and metal catalysts.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

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 Effects of substituents on the intramolecular hydrogen bond in 8-quinolinol-N-oxides, published in 1980-10-31, which mentions a compound: 1127-45-3, Name is 8-Hydroxyquinoline 1-oxide, Molecular C9H7NO2, SDS of cas: 1127-45-3.

IR spectral and deuteration studies on 8-quinolinol-N-oxides and its 5-nitro-, 5-nitroso-, 5-amino-, 5-phenylazo-, 5,7-dibromo- and 5,7-diiodo-derivatives in solid and in solution state confirm the presence of a strong intramol. unsym. H bond involving the hydroxyl hydrogen atom and the N-oxide oxygen atom. The structure of the complex absorption pattern in the region 2850 cm-1-1800 cm-1 is explained in terms of Fermi resonance interaction between the νOH of O-H…O and the overtone and combination bands of (δOH + νC-O) and other fundamental vibrations of the mol. The absence of any significant absorptions in the νOH region in the spectra of 5,7-dichloro- and 5,7-dinitro-derivatives coupled with strong and broad absorption in 1500 cm-1-600 cm-1 region is perhaps due to the presence of very short hydrogen bonds in these compounds

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Oh, Sangmi; Kim, Sungbum; Kong, Sunju; Yang, Gyongseon; Lee, Nakyung; Han, Dawoon; Goo, Junghyun; Siqueira-Neto, Jair L.; Freitas-Junior, Lucio H.; Song, Rita published the article 《Synthesis and biological evaluation of 2,3-dihydroimidazo[1,2-a]benzimidazole derivatives against Leishmania donovani and Trypanosoma cruzi》. Keywords: dihydroimidazobenzimidazole derivative preparation antileishmanial antitrypanosomal; 2,3-Dihydroimidazo[1,2-a]benzimidazole; Anti-parasitic activity; Chagas disease; Leishmaniasis.They researched the compound: 1-(Bromomethyl)-4-ethylbenzene( cas:57825-30-6 ).Electric Literature of C9H11Br. 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:57825-30-6) here.

A high-throughput (HTS) and high-content screening (HCS) campaign of a com. library identified 2,3-dihydroimidazo[1,2-a]benzimidazole analogs as a novel class of anti-parasitic agents. A series of synthetic derivatives were evaluated for their in vitro anti-leishmanial and anti-trypanosomal activities against Leishmania donovani and Trypanosoma cruzi, which were known as the causative parasites for visceral leishmaniasis and Chagas disease, resp. In the case of Leishmania, the compounds were tested in both intracellular amastigote and extracellular promastigote assays. Compounds I and II showed promising anti-leishmanial activity against intracellular L. donovani (3.05 and 5.29 μM, resp.) and anti-trypanosomal activity against T. cruzi (1.10 and 2.10 μM, resp.) without serious cytotoxicity toward THP-1 and U2OS cell lines.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Zhang, Qiao; Wang, Simin; Zhang, Qian; Xiong, Tao published the article 《Radical Addition-Triggered Remote Migratory Isomerization of Unactivated Alkenes to Difluoromethylene-Containing Alkenes Enabled by Bimetallic Catalysis》. Keywords: difluoromethyl alkene preparation diastereoselective; alkene radical addition isomerization.They researched the compound: 1-(Bromomethyl)-4-ethylbenzene( cas:57825-30-6 ).Quality Control of 1-(Bromomethyl)-4-ethylbenzene. 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:57825-30-6) here.

A fascinating alkene remote migratory isomerization engendered by carbon radical addition to C=C bond in alkenes Ar(CH2)nCH=CH2 (Ar = C6H5, 4-FC6H4, 2-pyridyl, etc.; n = 2, 4, 5, 6, 7) via bimetallic catalysis has been disclosed. A diverse array of alkenes bearing distantly incorporated the difluoromethylene ArCH=CH(CH2)mCF2C(O)R (m = 1, 4, 5, 6, 9; R = OMe, OEt, morpholin-4-yl, etc.) functionality have been expediently obtained. The retainment of C=C bonds in products could serve as an useful synthetic platform furnishing otherwise difficult to access value-added densely functionalized difluoromethylene containing mols. In addition, some exptl. studies have been implemented to shed light on the probable mechanism.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

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: 221012-82-4, is researched, SMILESS is COC(C=C1P(C2=CC=CC=C2)C3=CC=CC=C3)=NC(OC)=C1C4=C(OC)N=C(OC)C=C4P(C5=CC=CC=C5)C6=CC=CC=C6, Molecular C38H34N2O4P2Journal, Advanced Synthesis & Catalysis called Copper-Catalyzed Asymmetric Borylative Cyclization of Cyclohexadienone-Containing 1,6-Dienes, Author is He, Cheng-Yu; Li, Qing-Hua; Wang, Xin; Wang, Feng; Tian, Ping; Lin, Guo-Qiang, the main research direction is copper catalyzed asym borylative cyclization cyclohexadienone diene; borylated tetrahydrobenzofuranone preparation; crystal structure borylated tetrahydrobenzofuranone; mol structure borylated tetrahydrobenzofuranone.Category: quinoxaline.

Due to the low reactivity of 1,6-dienes and the challenge of selectively differentiating such two olefins, the development of metal-catalyzed asym. cyclization of 1,6-dienes remains largely underdeveloped. Herein, the authors describe the 1st Cu(I)-catalyzed asym. borylative cyclization of cyclohexadienone-tethered terminal alkenes (1,6-dienes) via a tandem process: the regioselective borocupration of the electron-rich terminal alkene and subsequent conjugate addition of stereospecific secondary alkyl-Cu(I) to the electron-deficient cyclohexadienone, affording enantioenriched bicyclic skeletons bearing three contiguous stereocenters in all cis-form. Meanwhile, this mild catalytic protocol is generally compatible with a wide range of functional groups, which allows further facile conversion of the cyclization products.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider