Tag: M.W:100-200

Electric Literature of C7H8N2O3. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 3,5-Dimethyl-4-nitropyridine 1-oxide, is researched, Molecular C7H8N2O3, CAS is 14248-66-9, about Heteroaromaticity. 8. The influence of N-oxide formation on heterocyclic aromaticity. Author is Bird, Clive W..

A recently described aromaticity index(author, 1992) has been used to examine the changes in the aromaticity of nitrogen heterocycles that accompany their N-oxidation Some instances are noted where there is an unforeseen increase in aromatic character. The aromaticity indexes is isomeric furoxans can be a useful indication as to their relative stabilities.

Although many compounds look similar to this compound(14248-66-9)Electric Literature of C7H8N2O3, numerous studies have shown that this compound(SMILES:O=[N+](C1=C(C)C=[N+]([O-])C=C1C)[O-]), has unique advantages. If you want to know more about similar compounds, you can read my other articles.

Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《The action of alkyl haloacetates on piperidine–the methyl chloroacetates》. Authors are Ursy, Yvette; Paty, Marcel.The article about the compound:1-Piperidineacetic Acidcas:3235-67-4,SMILESS:OC(=O)CN1CCCCC1).Application of 3235-67-4. Through the article, more information about this compound (cas:3235-67-4) is conveyed.

Piperidine (I) was treated, at room temperature in Et2O, with ClCH2CO2Me to give I.HCl, m. 244°. The filtrate on evaporation gave C5H10NCH2CO2Me (II), b23 92-3°, n20D 1.4559, d20 1.0103. Saponification of II and acidification gave C5H10NCH2CO2H, m. 214-16° (CHCl3); Na salt m. 280°; hydrochloride m. 217° (Et2O). I with Cl2CHCO2Me gave C5H10NCOCHCl2, m. 51°. I with an equimolar amount or excess Cl3CCO2Me gave C5H10NCOCCl3 (III), m 45°, and a small amount of I.HCl. With excess I, C5H10NCO2Me, b2 55-7°, n20D 1.4610, d20 1.053 (chloroplatinate m. 176°) was formed along with some III and I.HCl. The amount of I.HCl formed was in the proportions monochloro- > dichloro- > trichloroacetate.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Titanium(0) reagents. III. A convenient preparation of 4-pyridinamine derivatives》. Authors are Malinowski, Marek; Kaczmarek, Lukasz.The article about the compound:3,5-Dimethyl-4-nitropyridine 1-oxidecas:14248-66-9,SMILESS:O=[N+](C1=C(C)C=[N+]([O-])C=C1C)[O-]).Application In Synthesis of 3,5-Dimethyl-4-nitropyridine 1-oxide. Through the article, more information about this compound (cas:14248-66-9) is conveyed.

Ti(0) slurry, easily accessible by the reduction of TiCl4 with LiAlH4 or Mg in THF, is an excellent reagent for the reduction of N-nitropyridine N-oxides, e.g., I (R = H, Me, F, Cl) to 4-aminopyridines, e.g., II. The reaction proceeds smoothly and fast at room temperature giving the amines in >90% yields.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: (5-Nitropyridin-2-yl)methanol( cas:36625-57-7 ) is researched.Application of 36625-57-7.Achremowicz, Lucjan; Syper, Ludwik published the article 《Reactions of 3-nitropicolines N-oxides with acetic anhydride》 about this compound( cas:36625-57-7 ) in Roczniki Chemii. Keywords: picoline oxide acetic anhydride; nitro picoline oxide anhydride; pyridine aldehyde nitro. Let’s learn more about this compound (cas:36625-57-7).

The rearrangement of 2-methyl- (I), 4-methyl-3-nitropyridine N-oxide (II), and 2-methyl-5-nitropyridine N-oxide (III) in Ac2O gave a mixture of acetates. I acetate was hydrolysed with aqueous HCl to give 3-nitro-2-pyridylmethanol (IV), 2-methyl-3-nitropyridine, and 2-methyl-3-nitro-5-hydroxypyridine. From a similar reaction of II, 3-nitro-4-pyridylmethanol acetate was isolated. Rearrangement of III gave 5-nitro-2-pyridylmethanol acetate and two other compounds, which were hydrolysed with dilute HCl to give 5-nitro-2-pyridylmethanol (V) and 2-methyl-3-hydroxy-5-nitropyridine. Oxidation of IV or V with SeO2 in dioxane gave 3-nitro-2-picolinaldehyde hydrate and 5-nitro-2-picoline-aldehyde (32 and 70% resp.). A modified synthesis of 3-nitro-4-methylpyridine from 2,4-dimethylpyridine included its nitration to a mixture of 2,4- and 4,6-dimethyl-3-nitropyridine, which was transformed with 30% H2O2 in AcOH-C6H6, to the N-oxides, then rearranged in Ac2O to 4-methyl-3-nitro- and 4-methyl-5-nitro-2-pyridylmethanol acetate, hydrolysed with aqueous HCl to pyridylmethanols, oxidized with aqueous KMnO4 to give 4-methyl-3-nitropyridine-2-carboxylic acid and 4-methyl-5-nitropyridine-2-carboxylic aid. The acids were decarboxylated by heating at elevated temperature Nitration of 2,6-lutidine gave 3-nitro-2,6-lutidine, which was oxidized with KMnO4 to give 2-methyl-3-nitropyridine-6-carboxylic acid and subsequently decarboxylated to give 2-methyl-3-nitropyridine. 2-Methyl-5-nitropyridine was prepared from 2-chloro-5-nitropyridine by substitution with enolate anion (generated from diethyl malonate with metallic Na in xylene) followed by hydrolysis with aqueous H2SO4 and decarboxylation.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Benzoylacetamide and iminobenzoylacetamide》. Authors are Checchi, Silvio; Papini, Piero.The article about the compound:3,5-Dimethyl-4-nitropyridine 1-oxidecas:14248-66-9,SMILESS:O=[N+](C1=C(C)C=[N+]([O-])C=C1C)[O-]).Electric Literature of C7H8N2O3. Through the article, more information about this compound (cas:14248-66-9) is conveyed.

cf. CA 53, 21974b. BzCH2CN (I) was prepared in excellent yields from BzCH2CONH2 (II) and POCl3. Similar treatment of PhC(:NH)CH2CN (III) gave 6,3,2,4-Cl(CN)Ph2C5HN (IV), converted to give various 3,6-disubstituted 2,4-diphenylpyridines, N:CPh:CR:CPh.CH:CR’ (V). II (10 g.) and 18 g. POCl3 heated (H2O-free atm.) 30 min. on a steam bath at 60-70°, the cooled mixture decomposed with cold H2O, and the solid isolated and recrystallized repeatedly from H2O gave crystalline I, m. 70-2°. III (5 g.) and 8 g. POCl3 similarly heated 1 hr. at 70-80°, the cooled mass taken up in cold H2O, the washed (H2O, alc., Et2O) and dried product taken up in alc. containing a trace of HCl, and the crystalline material recrystallized from alc. yielded IV, m. 178-80°. IV (2 g.) refluxed 1 hr. in alc. containing 1 g. KOH and concentrated, the solution neutralized with dilute HCl, and the precipitate recrystallized from alc. gave V (R = CN, R’ = OH), m. 150°. IV (2 g.) heated 4 hrs. at 180° in a sealed tube with excess alc. NH3, the cooled mixture evaporated, and the product separated and recrystallized from ClCH:CCl2 yielded V (R = CN, R’ = NH2) hemihydrate, m. 214-15°. IV (5 g.) refluxed in alc. with powd. Zn, the filtered solution evaporated on a steam bath, and the residue taken up in a min. of HCONMe2 and diluted with H2O gave V(R = CN, R’ = H) (VI), m. 175-7° (alc.). VI (3 g.) heated 6 hrs. at 180-200° with concentrated HCl in a sealed tube, the liquid poured into hot H2O, the filtered solution neutralized with NH4OH, and the precipitate crystallized from alc. gave V(R = CO2H, R’ = H), m. 248-50°, decarboxylated by heating at 250° to V (R = R’ = H), characterized as the sulfate, m. 245° (darkening), and as the picrate, m. 187° (decomposition). IV (3 g.) refluxed 7 hrs. in 40% alc. KOH, the solvent evaporated, and the residue taken up in H2O and acidified with dilute HCl gave V (R = CONH2, R’ = OH), m. 287-9° (alc.), converted by heating 6 hrs. in a sealed tube at 180-90° with concentrated HCl to give V (R = H, R’ = OH), m. 210° (alc.) (also obtained similarly from IV); picrate m. 193-5° (alc.). VI (1 g.) boiled 2-3 min. in 4 ml. dilute H2SO4, the mixture boiled with addition of H2O, the cooled filtered solution made alk. with dilute NH4OH, and the precipitate crystallized from AcOEt and CHCl3 gave V (R = CONH2, R’ = H), m. 225-7°.

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Reference:
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.Wasylina, L.; Puszko, A. researched the compound: 3,5-Dimethyl-4-nitropyridine 1-oxide( cas:14248-66-9 ).Application In Synthesis of 3,5-Dimethyl-4-nitropyridine 1-oxide.They published the article 《Electronic spectra and structure of methyl derivatives of 4-nitropyridine N-oxide》 about this compound( cas:14248-66-9 ) in Chemistry of Heterocyclic Compounds (New York)(Translation of Khimiya Geterotsiklicheskikh Soedinenii). Keywords: methylnitropyridine oxide dipole moment intramol charge transfer. We’ll tell you more about this compound (cas:14248-66-9).

The UV spectra of seven Me derivatives of 4-nitropyridine N-oxide in ethanol have been examined The electronic spectra were calculated by a modified INDO method. Transition energies, intensities and assignments were compared with UV spectra. Spectroscopic manifestations of intramol. interaction indicate that Me groups modify the electronic interaction between the N-oxide and NO2 groups mainly through a steric strain.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Dega-Szafran, Z.; Kosturkiewicz, Z.; Nowak, E.; Petryna, M.; Szafran, M. published an article about the compound: 1-Piperidineacetic Acid( cas:3235-67-4,SMILESS:OC(=O)CN1CCCCC1 ).Electric Literature of C7H13NO2. 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:3235-67-4) through the article.

The 1-piperidineacetic acid was synthesized as monohydrate and its structure was determined by x-ray diffraction methods. The crystals are orthorhombic, space group P212121, a 6.7693(7), b 10.816(1), c 11.452(1) A, Z = 4, R = 0.037. The acid mol. appears in the zwitterionic form with two equivalent carboxylic O atoms. The water mols. link carboxylic groups into infinite chains parallel to the z axis, by O-H···O H bonds of the lengths 2.85(2) and 2.75(2) A. The N+(1)-H proton forms bifurcated H bond intramol. with O(1) and intermol. with O(2′) of the length 2.795(2) and 2.775(3) A, resp. Five of the most stable conformers of 1-piperidineacetic acid and four of its monohydrate were analyzed by B3LYP/6-31G(d,p) calculations For anhydrous acid, NPA1 conformer with intramol. N···H-O H bond is the most stable. The structure of conformer NPA1 is similar to that of the most stable conformer of N,N-dimethylglycine. The zwitterionic form, ZPA1, is stabilized by the electrostatic interaction between the pos. charged N+H and neg. charged O atoms of COO- group. ZPA1 is less stable than NPA1 and the energy difference between them is 23.8 kcal/mol. In the case of monohydrate the difference is only 4.6 kcal/mol. Addition of water mol. increases the stability of the zwitterionic form of 1-piperidineacetic acid, ZPAW3.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Name: 3,5-Dimethyl-4-nitropyridine 1-oxide. 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: 3,5-Dimethyl-4-nitropyridine 1-oxide, is researched, Molecular C7H8N2O3, CAS is 14248-66-9, about Systematic coordination chemistry and cytotoxicity of copper(II) complexes with methyl substituted 4-nitropyridine N-oxides. Author is Puszko, Aniela; Brzuszkiewicz, Anna; Jezierska, Julia; Adach, Anna; Wietrzyk, Joanna; Filip, Beata; Pelczynska, Marzena; Cieslak-Golonka, Maria.

Three new nitrato Cu(II) complexes of di-Me substituted 4-nitropyridine N-oxide were synthesized and characterized by elemental anal., magnetic, spectroscopic, thermal and x-ray methods, resp. They were isolated as trans isomers, mononuclear (μ = 1.70-1.88 μB), five-(1-2) and four-(3) coordinate species [Cu(NO3)2(H2O)L2] where L = 2,3-dimethyl- or 2,5-dimethyl-4-nitropyridine N-oxide and [Cu(NO3)2L2], L = 3,5-dimethyl-4-nitropyridine N-oxide, resp. The x-ray crystal structure of (1) (L = 2,3-dimethyl-4-nitropyridine N-oxide) was determined The organic ligands, the complexes and copper hexaqua ion as a reference were tested in vitro on the cytotoxic activity against human cancer cell lines: MCF-7 (breast), SW-707 (colon) and P-388 (murine leukemia). The complexes are relatively strong cytotoxic agents towards P-388 cell line. Comparative anal. was performed for all known Cu(II) complexes containing Me derivatives of the 4-nitropyridine N-oxide from their composition, structure and cytotoxic activities. To obtain the typical structure for these species (i.e., 4-coordinate mononuclear trans-[Cu(inorganic anion)2L2]), two Me groups must be situated on both sides of N atom(s) (i.e., NO and NO2) in the ligand. The biol. activity is strongly dependent upon the number of the Me groups and the type of cell line. The best cytotoxic results were found for the complexes without substituents or with one Me group. Generally, for all cell lines, the complexation increased cytotoxicity when compared with the free ligands.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Zhou, Huiyu; Zhu, Mei; Ma, Ling; Zhou, Jinming; Dong, Biao; Zhang, Guoning; Cen, Shan; Wang, Yucheng; Wang, Juxian published an article about the compound: 1-Piperidineacetic Acid( cas:3235-67-4,SMILESS:OC(=O)CN1CCCCC1 ).Computed Properties of C7H13NO2. 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:3235-67-4) through the article.

A series of potent HIV-1 protease inhibitors, containing diverse piperidine analogs as the P2-ligands, 4-substituted phenylsulfonamides as the P2′-ligands and a hydrophobic cyclopropyl group as the P1′-ligand, were designed, synthesized and evaluated in this work. Among these twenty-four target compounds, many of them exhibited excellent activity against HIV-1 protease with half maximal inhibitory concentration (IC50) values below 20 nM. Particularly, compound I containing a (R)-piperidine-3-carboxamide as the P2-ligand and a 4-methoxylphenylsulfonamide as the P2′-ligand exhibited the most effective inhibitory activity with an IC50 value of 3.61 nM. More importantly, I exhibited activity with inhibition of 42% and 26% against wild-type and Darunavir (DRV)-resistant HIV-1 variants, resp. Addnl., the mol. docking of I with HIV-1 protease provided insight into the ligand-binding properties, which was of great value for further study.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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 Periselectivity between the [1,4] and [3,3] thermal sigmatropic rearrangements of 2-allyloxypyridine N-oxides. Author is Alker, David; Ollis, W. David; Shahriari-Zavareh, Hooshang.

Thermal rearrangement of 2-allyloxpyridine N-oxides I (R = H, OMe, NO2) yields N-allyloxy-2-pyridones II and 3-allyl-N-hydroxy-2-pyridones III. These transformations are regiospecific and on this basis it is proposed that the reactions involve concerted [1,4] and [3,3] sigmatropic rearrangements. Supporting evidence based on solvent effects, temperature effects, and substituent effects is given.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem