Category: 2402-95-1

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 2-Chloropyridine 1-oxide( cas:2402-95-1 ) is researched.Application of 2402-95-1.Kim, Inwon; Kang, Gyumin; Lee, Kangjae; Park, Bohyun; Kang, Dahye; Jung, Hoimin; He, Yu-Tao; Baik, Mu-Hyun; Hong, Sungwoo published the article 《Site-Selective Functionalization of Pyridinium Derivatives via Visible-Light-Driven Photocatalysis with Quinolinone》 about this compound( cas:2402-95-1 ) in Journal of the American Chemical Society. Keywords: phosphorylpyridine pyridinecarboxamide green regioselective photochem preparation; regioselective photochem phosphonylation carbamoylation pyridine azine phosphonylquinolinone photocatalyst; oxidative photochem regioselective phosphonylation carbamoylation pyridine; transition state structure free energy regioselective phosphonylation carbamoylation pyridine; mechanism regiochem regioselective photochem phosphonylation carbamoylation pyridine. Let’s learn more about this compound (cas:2402-95-1).

In the presence of phosphonylquinolinone I, N-ethoxypyridinium and N-ethoxyazinium tetrafluoroborates such as II underwent green and regioselective visible light-mediated photochem. oxidative phosphonylation and carbamoylation reactions with phosphinous acids and formamides mediated by K2S2O8 and NaHCO3 at ambient temperature to give pyridinyl- and azinyl phosphine oxides such as III and pyridine- and azinecarboxamides such as IV. Under the standard reaction conditions, phosphinoyl radicals give access to C4-substituted pyridines, while carbamoyl radicals selectively give 2-pyridinecarboxamides. The mechanism of the reaction was studied using DFT calculations and radical inhibition, fluorescence quenching, and kinetic isotope effect experiments The carbamoyl radical overcomes the intrinsic preference for forming the ortho-product by allowing the oxo functionality of the carbamoyl radical to electrostatically engage the nitrogen of the pyridinium substrate, preferentially giving the ortho-product; the phosphinoyl radical cannot engage in the same interaction because the phosphorus atom is too large.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2-Chloropyridine 1-oxide, is researched, Molecular C5H4ClNO, CAS is 2402-95-1, about Reaction of chloropyridine N-oxides with potassium amide in liquid ammonia, the main research direction is AMIDES; AMMONIA; CHEMISTRY, PHARMACEUTICAL; EXPERIMENTAL LAB STUDY; POTASSIUM; PYRIDINES.Category: isoxazole.

2-Chloropyridine 1-oxide forms 2-aminopyridine 1-oxide (m. 163-4°) and 3-aminopyridine 1-oxide (m. 119-20°), though in a low yield, on treatment with liquid NH3 in the presence of KNH2. Under the same conditions, 3- and 4-chloropyridine 1-oxides give only the 3- and 4-amino compound (m. 64 and 154-5°, resp.), resp. Thus, the mechanism of these reactions is entirely the reverse of that of chloropyridine reported by Hertog (Pieterse and H., CA 58, 11325a; Martens and H., CA 58, 7902a); that of the 2-chloro compound is a benzyne mechanism and that of the 3- and 4-chloro compounds is an amination by an SN2 mechanism.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Sojka, Stanley A.; Dinan, Frank J.; Kolarczyk, Robert published an article about the compound: 2-Chloropyridine 1-oxide( cas:2402-95-1,SMILESS:ClC1=CC=CC=[N+]1[O-] ).Computed Properties of C5H4ClNO. 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:2402-95-1) through the article.

13C NMR spectra of substituted pyridine N-oxides were examined and compared to the spectra of the corresponding free pyridine bases. The N-oxide functionality causes significant shielding at the C-2, C-4, and C-6 positions. This shielding was associated with electron d. donation by the N-oxide functionality to these positions. The N-oxide functionality also caused an enhancement of the substituent α-effect for -NMe2, -OMe, and -NO2 groups.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – 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, Advanced Synthesis & Catalysis called Aqueous biphasic oxidation: a water-soluble polyoxometalate catalyst for selective oxidation of various functional groups with hydrogen peroxide, Author is Sloboda-Rozner, Dorit; Witte, Peter; Alsters, Paul L.; Neumann, Ronny, which mentions a compound: 2402-95-1, SMILESS is ClC1=CC=CC=[N+]1[O-], Molecular C5H4ClNO, Recommanded Product: 2-Chloropyridine 1-oxide.

A “”sandwich”” type polyoxometalate, Na12[WZn3(H2O)2][(ZnW9O34)2], was used as an oxidation catalyst in aqueous biphasic reaction media to effect oxidation of alcs., diols, pyridine derivatives, amines and aniline derivatives with hydrogen peroxide. The catalyst was shown by 183W NMR to be stable in aqueous solutions in the presence of H2O2 and showed only minimal non-productive decomposition of the oxidant. Secondary alcs. were selectively oxidized to ketones, while primary alcs. tended to be oxidized to the corresponding carboxylic acids, although secondary alcs. were selectively oxidized in the presence of primary alcs. Vicinal diols yielded carbon-carbon bond cleavage products in very high yields. Pyridine derivatives were oxidized to the resp. N-oxides, but strongly electron-withdrawing moieties inhibited the oxidation reaction. Primary amines were oxidized to the oximes, but significantly hydrolyzed in situ. Aniline derivatives were oxidized to the corresponding azoxy or nitro products depending on the substitution pattern in the aromatic ring. Catalyst recovery and recycle was demonstrated.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Deng, Nan; Jiang, Zhong-liang; Wang, Yu; Guo, Yi-ping researched the compound: 2-Chloropyridine 1-oxide( cas:2402-95-1 ).Formula: C5H4ClNO.They published the article 《Improved synthesis of zinc pyridine-2-thiol-N-oxide》 about this compound( cas:2402-95-1 ) in Jingxi Yu Zhuanyong Huaxuepin. Keywords: zinc pyridine thiol oxide preparation antibacterial. We’ll tell you more about this compound (cas:2402-95-1).

At first the raw material of title compound, 2-chloropyridine-N-oxide was synthesized using 2-chloropyridine as starting material, acetic acid and hydrogen peroxide as oxidants. Then the final zinc pyridine-2-thiol-N-oxide was obtained starting from 2-chloropyridine-N-oxide via the reactions such as thiolation, preparing sodium salt, reacting with zinc sulfate and so on. And the structure of product was characterized by H NMR and MS. Finally, the optimum reaction conditions were obtained through series experiments

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

COA of Formula: C5H4ClNO. 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: 2-Chloropyridine 1-oxide, is researched, Molecular C5H4ClNO, CAS is 2402-95-1, about Study in synthesis of N-oxide-2-pyridine phenyl sulfide derivative. Author is Li, Shuyan.

N-oxide-2-pyridine Ph sulfide derivatives were prepared by mercapto-reaction of 4-methylthiophenol or 4-chlorothiophenol with N-oxide-2-chloropyridine prepared by oxygenation of 2-chloropyridine with 30% H2O2 in acetic acid. The reaction of nucleophilic displacement on the ring of 2-chloropyridine was discussed. The structures of the synthesized compounds were characterized by IR, 1H NMR, and 13C NMR.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – 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 Aromatic fluorine compounds. IX. 2-Fluoropyridines, published in 1959, which mentions a compound: 2402-95-1, Name is 2-Chloropyridine 1-oxide, Molecular C5H4ClNO, Quality Control of 2-Chloropyridine 1-oxide.

cf. C.A. 53, 13090c. Anhydrous KF (I) 9 g., 12.3 g. 2-chloro-3-nitropyridine and 30 ml. HCONMe2 (DMF) was heated 6 hrs. at 150°, cooled, the mixture poured onto crushed ice, saturated with NaCl, steam distilled, the distillate extracted with Et2O, dried and distilled to give 8.4 g. 2-fluoro-3-nitropyridine, b10 109-9.5° n25D 1.5278. I (73.3 g.) added to a stirred solution of 100 g. 2-chloro-5-nitropyridine and 300 ml DMF at 120°, cooled and processed as above gave 70.1 g. 2-fluoro-5-nitropyridine b7 86-7°, n25D 1.5243. NaNO2 (13.3 g.) in 65 ml. H2O added dropwise with stirring at -2° to 0° to 28 g. 2-amino-3-bromo-5-nitropyridine in aqueous H2SO4 (25%, 900 ml.), the mixture boiled, filtered and cooled gave 18.3 g. 3-bromo-5-nitropyridine (II), m. 212° (decomposition) (H2O). II (4.1 g.), 4 g. PCl3 and 1 ml. POCl3 stirred and refluxed 3 hrs., the mixture concentrated in vacuo and poured onto crushed ice gave 4.2 g. 3-bromo-2-chloro-5-nitropyridine (III), m. 67.3-8.0° after sublimation at 60-70° 2 mm. A stirred mixture of 3.8 g. III, 15 ml. DMF and 1.8 g. I was heated 1 hr. at 100° cooled, poured onto ice, steam distilled, the distillate extracted with Et2O, dried and evaporated to give 2.5 g. crude 3-bromo-2-fluoro-5-nitropyridine; this repeatedly vacuum sublimed gave 1.78 g. pure product, m. 60-1.5° Peracetic acid (40%, 137 ml.) was added dropwise to a stirred solution of 50 g. 2-chloropyridine (IV) and 66 ml. glacial AcOH at 45° the mixture heated 5 hrs. at 50° and 17 hrs. at 70°, concentrated in vacuo to 150 ml. on a steam-bath, poured onto crushed ice, made strongly alk. with 40% NaOH, extracted with CHCl3 dried with MgSO4 and a small amount Na2CO3, the extract evaporated and diluted with 10 ml. anhydrous Et2O gave 45.8 g. 2-chloropyridine N-oxide (V), m. 69-9.5° (Et2O-EtOH). To a mixture obtained by adding 10 g. V to 15 ml. concentrated H2SO4 was added with stirring at 1-2° over 45 min. a mixture of 15 ml. concentrated H2SO4 and 27 ml. fuming HNO3 (sp. gr. 1.5), the mixture heated over 1 hr. to 90°, stirred 1 hr. at 90° cooled to 10° poured onto stirred ice-H2O, neutralized with Na2CO3, filtered, the yellow precipitate partially air dried, dissolved in hot CHCl3, the aqueous filtrate extracted with CHCl3 and the combined CHCl3 solutions dried and evaporated to give 11.4 g. crude 2-chloro-4-nitropyridine N-oxide (VI) m. 153-3.5° (EtOH-CHCl3.) 2-Chloro-4-nitropyridine (VII) was obtained in 91% yield by Hamana procedure (C.A. 50, 1817a). VII (5 g.), 3.7 g. I and 10 ml. di-Me sulfoxide gave a good halide test after being heated 1 hr. at 160°; the mixture was cooled, poured onto crushed ice, saturated with NaCl, steam distilled The distillate was extracted repeatedly with CHCl3; the combined extracts dried and evaporated gave no residue, but the pot residue from the steam distillation gave a small portion of solid, unidentified, m. 100.5-5.0° after sublimation. VII and di-Me sulfoxide in the absence of I gave no evidence of reaction. Dry HCl was passed 2.25 hrs. into a stirred solution of 20 g. IV in 200 ml. anhydrous Et2O and the Et2O evaporated in vacuo to leave 23.4 g. hygroscopic needles, 2-chloropyridine-HCl m. 101.5-2.0°, decomposing on standing, darkening on exposure to light.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2-Chloropyridine 1-oxide(SMILESS: ClC1=CC=CC=[N+]1[O-],cas:2402-95-1) is researched.Recommanded Product: 1-Piperidineacetic Acid. The article 《2-Hydroxypyridine-N-oxide (HOPO): Equivocal in the ames assay》 in relation to this compound, is published in Environmental and Molecular Mutagenesis. Let’s take a look at the latest research on this compound (cas:2402-95-1).

2-Hydroxypyridine-N-oxide (HOPO) is a useful coupling reagent for synthesis of active pharmaceutical ingredients. It has been reported to be weakly mutagenic in the Ames assay (Ding W et al. []: J Chromatogr A 1386:47-52). According to the ICH M7 guidance (2014) regarding control of mutagenic impurities to limit potential carcinogenic risk, mutagens require control in drug substances such that exposure not exceeds the threshold of toxicol. concern. Given the weak response observed in the Ames assay and the lack of any obvious structural features that could confer DNA reactivity we were interested to determine if the results were reproducible and investigate the role of potentially confounding exptl. parameters. Specifically, Ames tests were conducted to assess the influence of compound purity, solvent choice, dose spacing, toxicity, type of S9 (aroclor vs phenobarbital/β-naphthoflavone), and lot variability on the frequency of HOPO induced revertant colonies. Initial extensive testing using one lot of HOPO produced no evidence of mutagenic potential in the Ames assays. Subsequent studies with four addnl. lots produced conflicting results, with an ∼2.0-fold increase in revertant colonies observed Given the rigor of the current investigation, lack of reproducibility between lots, and the weak increase in revertants, it is concluded that HOPO is equivocal in the bacterial reverse mutation assay. It is highly unlikely that HOPO poses a mutagenic risk in vivo; therefore, when it is used as a reagent in pharmaceutical synthesis, it should not be regarded as a mutagenic impurity, but rather a normal process related impurity.

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Isoxazole – Wikipedia,
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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 Synthesis of 4-amino-2-chloropyridine, published in 2005-09-30, which mentions a compound: 2402-95-1, Name is 2-Chloropyridine 1-oxide, Molecular C5H4ClNO, Formula: C5H4ClNO.

4-Amino-2-chloropyridine was synthesized from 2-chloropyridine by oxidation with hydrogen peroxide and nitration with fuming nitric acid to give 2-chloro-4-nitropyridine-N-oxide followed by reduction in 75% overall yield.

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Reference of 2-Chloropyridine 1-oxide. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2-Chloropyridine 1-oxide, is researched, Molecular C5H4ClNO, CAS is 2402-95-1, about MO calculations on heterocycles. 21. Interpretation of the photoelectron spectra of substituted pyridine-N-oxides. Author is Scholz, Manfred; Goetze, Raimund; Kluge, Gert; Klasinc, Leo; Novak, Igor.

The He I and He II photoelectron spectra of I (R = H; 2-, 3-, 4-Cl; 2-, 3-, 4-Me) were interpreted by a modified CNDO MO method. With a suitably chosen symmetry anal. an assignment in the MO ionization picture is possible for all mols. up to ∼15 eV.

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