Month: April 2022

SDS of cas: 1195-58-0. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: Pyridine-3,5-dicarbonitrile, is researched, Molecular C7H3N3, CAS is 1195-58-0, about Oxidation of organic compounds. XCIV. Synthesis of 3,5-dicyanopyridine by the oxidative ammonolysis of 3,5-butidine. Author is Suvorov, B. V.; Kagarlitskii, A. D.; Belova, N. A.; Kutzhanov, R. T..

Ammoxidation of 3,5-lutidine (I) using 1:9:17 I-O-NH3 at 350° in the presence of fused vanadium oxide-titanium oxide with a 0.5 sec contact time gave 40% 3,5-pyridinedicarbonitrile (II) and 5-methyl-3-pyridinecarbonitrile. Hydrolysis of II in aqueous NaOH gave 3,5-pyridinedicarboxylic acid.

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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 3-Bromo-4-chloronitrobenzene( cas:16588-26-4 ) is researched.Recommanded Product: 16588-26-4.Liedholm, Brita published the article 《Copper(I)-induced bromine-hydrogen exchange of 2,3-dibromoanilines》 about this compound( cas:16588-26-4 ) in Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry. Keywords: copper reduction dibromoaniline; aniline dibromo debromination copper; debromination dibromoaniline copper ion. Let’s learn more about this compound (cas:16588-26-4).

The Cu(I)-induced Br/H exchange reaction of 2,3-dibromoaniline and 5-substituted 2,3-dibromoanilines in the 2-position has been kinetically studied in aqueous HOAc-HCl medium at 90°. The dehalogenation reaction is 2nd order, 1st in both substrate and Cu+, and may be interpreted as a reductive substitution, composed of two 1-electron steps. The 2,3-dibromophenol was only qual. examined but gave similar results.

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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: (5aS,10bR)-2-(2,6-Diethylphenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate( cas:1787246-78-9 ) is researched.Category: alcohols-buliding-blocks.Hovey, M. Todd; Cohen, Daniel T.; Walden, Daniel M.; Cheong, Paul H.-Y.; Scheidt, Karl A. published the article 《A Carbene Catalysis Strategy for the Synthesis of Protoilludane Natural Products》 about this compound( cas:1787246-78-9 ) in Angewandte Chemie, International Edition. Keywords: carbene catalysis mellolide protoilludane marasmane sesquiterpenoid synthesis; N-heterocyclic carbenes; armillaridin; marasmane; protoilludane; total synthesis. Let’s learn more about this compound (cas:1787246-78-9).

The Armillaria and Lactarius genera of fungi produce the antimicrobial and cytotoxic mellolide, protoilludane, and marasmane sesquiterpenoids. We report a unified synthetic strategy to access the protoilludane, mellolide, and marasmane families of natural products. The key features of these syntheses are (1) the organocatalytic, enantioselective construction of key chiral intermediates from a simple achiral precursor, (2) the utility of a key 1,2-cyclobutanediol intermediate to serve as a precursor to each natural product class, and (3) a direct chem. conversion of a protoilludane to a marasmane (I → II) through serendipitous ring contraction, which provides exptl. support for their proposed biosynthetic relationships.

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Safety of (5aS,10bR)-2-(2,6-Diethylphenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate. 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: (5aS,10bR)-2-(2,6-Diethylphenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate, is researched, Molecular C22H24BF4N3O, CAS is 1787246-78-9, about Switchable Access to Different Spirocyclopentane Oxindoles by N-Heterocyclic Carbene Catalyzed Reactions of Isatin-Derived Enals and N-Sulfonyl Ketimines. Author is Wang, Lei; Li, Sun; Bluemel, Marcus; Puttreddy, Rakesh; Peuronen, Anssi; Rissanen, Kari; Enders, Dieter.

A novel NHC-catalyzed annulation protocol for the asym. synthesis of biol. important β-lactam fused spirocyclopentane oxindoles with four contiguous stereocenters, including two quaternary carbon centers, was developed. Alternatively, spirocyclopentane oxindoles containing an enaminone moiety can be achieved using the same starting materials, isatin-derived enals, and N-sulfonyl ketimines, in the presence of a slightly different NHC catalytic system. This switchable annulation strategy enables the selective assembly of both heterocyclic scaffolds with good yields and excellent enantioselectivities for a broad range of substrates.

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Safety of 1-(4-Chlorophenyl)pyrrolidin-2-one. 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: 1-(4-Chlorophenyl)pyrrolidin-2-one, is researched, Molecular C10H10ClNO, CAS is 7661-33-8, about Selective cleavage and reconstruction of C-N/C-C bonds in saturated cyclic amines: tunable synthesis of lactams and functionalized acyclic amines. Author is He, Yan; Yang, Jintao; Zhang, Xinying; Fan, Xuesen.

Selective cleavage and functionalization of C-N/C-C bonds in saturated cyclic amines under the promotion of oxoammonium salt and tert-Bu hydroperoxide in the presence of different additives was developed. To be specific, cascade cleavage and reconstruction of C-N and C-C bonds took place under acidic conditions to provide pyrrolidin-2-ones. Under basic conditions, on the other hand, selective cleavage and functionalization of C-C bonds occurred to afford multi-functionalized acyclic N-formal amines. In addition, studies for revealing the intriguing reaction mechanisms was also been performed.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《On cyclic intermediates in substitution reactions. VII. The alkaline solvolysis of some N-aryl-4-bromobutanamides》. Authors are Heine, Harold W.; Love, Peter; Bove, John L..The article about the compound:1-(4-Chlorophenyl)pyrrolidin-2-onecas:7661-33-8,SMILESS:O=C1N(C2=CC=C(Cl)C=C2)CCC1).Category: alcohols-buliding-blocks. Through the article, more information about this compound (cas:7661-33-8) is conveyed.

cf. C.A. 49, 1556b. The rates of the solvolysis of 3 N-aryl-4-bromobutanamides have been studied in MeOH. The rates of the reaction as determined by the measurement of the release of bromide ion are 1st order with respect to MeO-. The reaction products are the corresponding pyrrolidones. These results are discussed in terms of a mechanism involving the formation and conversion of a bromoamido ion to a pyrrolidone. SOCl2 (20 cc.) added dropwise to 37.1 g. Br(CH2)3CO2H, the mixture held 2 days at room temperature, the excess SOCl2 removed in vacuo, and the residue distilled gave a distillate, b31 88-90°, nD201.4899; a 37.1-g. sample of the distillate added dropwise with stirring to 37.2 g. PhNH2 in 500 cc. CHCl3, the mixture stirred 15 min., the precipitate filtered and washed with CHCl3, the combined filtrate and washing concentrated in vacuo, and the crude residue dissolved in ligroine, b. 65-110°, cooled, and then chilled to -78° gave 38% Br(CH2)3CONHPH (I), m. 75-6°. In the same manner except with a reaction time of 4 hrs. was prepared the p-Me derivative (II) of I, m. 90-1° (from petr. ether), in 63.2% yield. The p-Cl derivative (III) of I, m. 100-1° (from petr. ether), was prepared with a reaction time of 2 hrs. in 69.2% yield. A solution (100 cc.) 0.05M in NaOMe and 0.05M in III kept at 22.9° until all bromide ion had been released, the MeOH evaporated in vacuo, the residue washed with H2O, and the residue dried at 50° and recrystallized from petr. ether (b. 30-60°) gave 0.940 g. 1-(p-chlorophenyl)pyrrolidone (IV), m. 95-7°. The average rate constants of the alk. solvolyses determined at 22.90° were: III 5.65, I 1.80, and II 1.03 × 10 l./min./mole.

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Name: 1-(4-Chlorophenyl)pyrrolidin-2-one. 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: 1-(4-Chlorophenyl)pyrrolidin-2-one, is researched, Molecular C10H10ClNO, CAS is 7661-33-8, about Late-stage oxidative C(sp3)-H methylation. Author is Feng, Kaibo; Quevedo, Raundi E.; Kohrt, Jeffrey T.; Oderinde, Martins S.; Reilly, Usa; White, M. Christina.

Frequently referred to as the ‘magic Me effect’, the installation of Me groups-especially adjacent (α) to heteroatoms-has been shown to dramatically increase the potency of biol. active mols.1-3. However, existing methylation methods show limited scope and have not been demonstrated in complex settings1. Here, we report a regioselective and chemoselective oxidative C(sp3)-H methylation method that is compatible with late-stage functionalization of drug scaffolds and natural products. This combines a highly site-selective and chemoselective C-H hydroxylation with a mild, functional-group-tolerant methylation. Using a small-mol. manganese catalyst, Mn(CF3PDP), at low loading (at a substrate/catalyst ratio of 200) affords targeted C-H hydroxylation on heterocyclic cores, while preserving electron-neutral and electron-rich aryls. Fluorine- or Lewis-acid-assisted formation of reactive iminium or oxonium intermediates enables the use of a mildly nucleophilic organoaluminum methylating reagent that preserves other electrophilic functionalities on the substrate. We show this late-stage C(sp3)-H methylation on 41 substrates housing 16 different medicinally important cores that include electron-rich aryls, heterocycles, carbonyls and amines. Eighteen pharmacol. relevant mols. with competing sites, including drugs (for example, tedizolid) and natural products, are methylated site-selectively at the most electron rich, least sterically hindered position. We demonstrate the syntheses of two magic Me substrates, an inverse agonist for the nuclear receptor RORc and an antagonist of the sphingosine-1-phosphate receptor-1, via late-stage methylation from the drug or its advanced precursor. We also show a remote methylation of the B-ring carbocycle of an abiraterone analog. The ability to methylate such complex mols. at late stages will reduce synthetic effort and thereby expedite broader exploration of the magic Me effect in pursuit of new small-mol. therapeutics and chem. probes.

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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: 1195-58-0, is researched, SMILESS is N#CC1=CC(C#N)=CN=C1, Molecular C7H3N3Journal, Journal of Heterocyclic Chemistry called Correlation of 2-, 3-, 4- and disubstituted pyridine gas-phase proton affinities with ab initio calculated energies at the STO-3G basis set level, Author is Caronna, Tullio; Vittimberga, Bruno M., the main research direction is proton affinity pyridine derivative energy calculation; ab initio protonation pyridine energy.Recommanded Product: Pyridine-3,5-dicarbonitrile.

Total energies of 2-, 3-, 4- and disubstituted pyridines were calculated for the salt and the free base using ab initio MO calculations at the STO-3G basis set level. In each set, the difference in energy, ΔEH, between the salt and the free base was calculated and plotted against exptl. derived gas-phase proton affinities. The correlation was very good for each of the substituent categories listed. All of the energies and proton affinities were then plotted together on the same graph. The result was an excellent correlation with r = 0.97. The linear equation for gas phase proton affinity, PAB = 28.51 + 435.45ΔEH kcal/mol, was derived from this plot and was used to calculate proton affinities for all 31 compounds used in this study as well as for a series of dicyanopyridines for which values of proton affinity are not available at this time.

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Application of 651780-02-8. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: tert-Butyl 5-bromo-1H-indazole-1-carboxylate, is researched, Molecular C12H13BrN2O2, CAS is 651780-02-8, about The application of nitrogen heterocycles in mitochondrial-targeting fluorescent markers with neutral skeletons. Author is Wang, Yue; Xu, Bing; Sun, Ru; Xu, Yu-Jie; Ge, Jian-Feng.

Four different neutral fluorescent markers containing nitrogen heterocycles (quinoxaline, 1H-pyrazolo[3,4-b]pyridine, 1H-indazole and 1H-pyrrolo[2,3-b]pyridine) as targeting groups were designed and prepared in order to screen out structural units for targeting mitochondria. Several classical fluorophores (coumarin, 1,8-naphthalimide and Nile Red) were connected with these heterocycles via Suzuki coupling reactions. The derivatives of coumarin (dyes 1a and 2a-c) and 1,8-naphthalimide (dyes 3a-c) fluoresced in the blue-green region, while the Nile Red derivatives (dyes 1b and 4a-c) fluoresced in the red light region. The optical properties of the classical fluorophores, such as emission properties and photostability, were retained in the new dyes. All of them showed low cytotoxicity. Confocal fluorescence experiments in L929 normal cells and HeLa cancer cells indicated that dyes 1a-b targeted dual sites of mitochondria and lipid droplets. Moreover, dyes 2a-c, 3a-c and 4a-c targeted mitochondria; meanwhile, there are only a few mitochondria-targeting markers with neutral skeletons. Furthermore, it was found that nitrogen heterocycles with N-H bonds can improve the mitochondrial targeting ability of partial neutral fluorophores.

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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 Structure-Activity Relationships for the Glutathione Conjugation of 2-Substituted 1-Chloro-4-nitrobenzenes by Rat Glutathione S-Transferase 4-4, published in 1996-03-31, which mentions a compound: 16588-26-4, Name is 3-Bromo-4-chloronitrobenzene, Molecular C6H3BrClNO2, HPLC of Formula: 16588-26-4.

In the present study structure-activity relationships (SAR’s) are described for the exptl. determined kinetic parameters (Km, kcat, and kcat/Km) of the GST 4-4-catalyzed reaction between GSH and 10 2-substituted 1-chloro-4-nitrobenzenes. Steric, lipophilic, and electronic parameters were correlated with the kinetic parameters. Moreover, charge distributions and several energy values were calculated for the substrates and the corresponding Meisenheimer intermediates with MeS- as a model nucleophile for the thiolate anion of GSH and used in the regression analyses. The correlations obtained were compared with the corresponding SAR’s for the base-catalyzed GSH conjugation reaction at pH 9.2. A high correlation coefficient was found between the kinetic parameter ks for the base-catalyzed reaction and the Hammett substituent constant (σp). Much lower correlation coefficients were obtained with kcat and σp and with kcat/Km and σp. Moreover, the reaction constant ρ was significantly higher for the base-catalyzed than for the enzyme-catalyzed reaction. Also, high correlations were found between the kinetic parameters and the charges on the p-nitro substituent in the substrates. When ks was plotted against these charges, a linear relation was found in which the slope was larger than the slope of a corresponding plot with kcat/Km. The Hammett σp can be divided into an inductive (F) and a resonance (R) component. With multiple regression between the kinetic parameters and F and R, higher correlation coefficients were obtained than with σp alone. The observations suggest that the transition states for the base-catalyzed and the GST 4-4-catalyzed GSH conjugation reaction are different. Moreover, single classical physicochem. and computer-calculated mol. parameters and combinations of them can be an alternative approach for examining SAR’s for spontaneous and GST-catalyzed GSH conjugation reactions.

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