Tag: M.W=100-150

Suzuki, Yasuyuki published the artcileReactions of 4-pyridine- and 4-quinolinesulfonic acids with amines, Synthetic Route of 18437-58-6, the publication is Yakugaku Zasshi (1961), 1146-50, database is CAplus.

4-Pyridinesulfonic acid, 4-HO₃SC₅H₄N, (I) (1.6 g.) in 16 ml. 28% NH₄OH and a small amount of ZnCl₂ in an autoclave heated 2 hrs. at 150-60° cooled, 10 ml. 2N NaOH added, the NH₄OH removed and the product extracted with CHCl₃ gave 0.65 g. 4H₂NC₅H₄N, m. 157-8°. 2,4-Me(HO₃S)C₅H₃N (3 g.), 30 ml. 28% NH₄OH and a small amount ZnCl₂ in an autoclave heated 24 hrs. at 150-60° and the product treated as above gave 1.21 g. 2,4-Me(H₂N)C₅H₃N, m. 94-5°. Similarly prepared were the following amino compounds (product, % yield, and m.p. given): 3,4-Me(H₂N)C₅H₃N, 57.2, 107.5-9.0°; 2,6,4-Me₂(H₂N)C₅H₂N, 70.8, 192-3°; [from 4-HO₃SC₉H₆N (II)] 4-H₂NC₉H₆N, 79.5, 153°. I (1.6 g.), 10 ml. 33% MeNH₂ and a small amount of ZnCl₂ heated 24 hrs. at 130° gave 0.87 g. 4-MeNHC₅H₄N; picrate, m. 122-4°. Similarly, I and Me₂NH yielded 72.5% 4-Me₂NC₅H₄N, m. 112-13° (picrate, m. 204°); II and MeNH₂ yielded 88.3% 4-MeNHC₉H₆N, m. 224°; II and Me₂NH yielded 76.3% 4-Me₂NC₉H₆N, b₁₀ 167° (picrate, m. 192°). 2-HO₃SC₅H₄N (1.6 g.), 3.2 ml. 80% N₂H₄.H₂O, 7 ml. H₂O, and a small amount of ZnCl₂ in an autoclave heated 24 hrs. at 100-5°, the solution filtered, the filtrate concentrated in vacuo, the residue in 10 ml. 50% KOH extracted with Et₂O, and the picrate formed gave 2.1 g. 2-H₂NNHC₅H₄N picrate, m. 162-3° (decomposition). Similarly prepared were the following hydrazine derivatives (starting material, product, % yield and m.p. or m.p. of its salt given): I, 4-H₂NNHC₅H₄N (III), 72, HCl salt, 242-4°; 2-HO₃SC₉H₆N, 2-H₂NNHC₉H₆N, 64.5, picrate, 187-9° (decomposition); II, 4-H₂NNHC₉H₆N (IV), 81.2, HCl salt, 3078°; 2,4-Me(HO₃S)C₉H₅N, 2,4-Me(H₂NNH)C₉H₅N, 73.3, picrate, 206° (decomposition). 4-H₂NNHC₉H₆N.HCl (0.5 g.) in 10 ml. H₂O, 2 ml. EtOH and 1 ml. 10% NaOH, while refluxing, treated dropwise with 15 ml. 10% CuSO₄, refluxed 1 hr., refluxed 1 hr. with 5 ml. 10% NaOH and the product steam distilled gave 0.25 g. C₉H₇N; picrate, m. 202-3°. III.HCl (1 g.) in 50 ml. absolute EtOH treated with EtONa (0.16 g. Na and 7 ml. EtOH), the NaCl removed, the solution concentrated to 10 ml., refluxed 1 hr. with 0.8 g. Et pyruvate and the product concentrated gave 1.05 g. Et pyruvate 4-pyridylhydrazone, columns, m. 128-30°. III.HCl (1.45 g.) in 40 ml. MeOH treated with 1 g. KSCN in 10 ml. MeOH, refluxed 9 hrs. and the product concentrated gave 1.4 g. III.HSCN, m. 1079°. III (from 1.6 g. III.HCl) in 10 ml. C₅H₅N at 0° treated dropwise with 1.55 g. BzCl, stirred 1 hr. at room temperature, kept overnight, the solvent removed, and the residue washed with H₂O gave 1.2 g. 4-pyridyldibenzoylhydrazine, m. 2345° (EtOH). III (from 1.45 g. III.HCl) in 10 ml. EtOH and 1 g. AcCH₂COMe refluxed 1 hr., the EtOH removed, the residue in 5 ml. 10% NaOH and 10 ml. H₂O extracted with CHCl₃ and the product distilled gave 1.15 g. 1-(4-pyridyl)3,5-dimethylpyrazole, b₅ 131-4°; picrate m. 237° (decomposition). A solution of 1.26 g. AcONa.3H₂O, 3 ml. H₂O, 1 g. IV.HCl, 0.37 g. Me₂CO and 1 ml. AcOH refluxed 1.5 hrs., cooled, 4 ml. H₂O added and the mixture made alk. with NH₄OH and kept overnight at 0° gave 0.62 g. acetone 4-quinolylhydrazone, m. 122°. IV (0.5 g.) in 5 ml. EtOH and 0.34 g. PhCHO refluxed 1 hr. and the product concentrated gave 0.46 g. benzaldehyde 4-quinolylhydrazone, m. 11314°. IV.HCl (0.9 g.) in 20 ml. H₂O, 0.63 g. AcONa.3H₂O and 0.4 g. pyruvic acid mixed well and the product filtered off gave 0.73 g. pyruvic acid 4-quinolylhydrazone, m. 246° (decomposition). IV (0.35 g.) in 4 ml. EtOH and 0.25 g. Et pyruvate refluxed 1 hr. and the solution concentrated gave 0.31 g. Et pyruvate 4-quinolylhydrazone, m. 178°. IV.HCl (1.4 g.), 0.7 g. KSCN, and 50 ml. MeOH refluxed 12 hrs. and the solution concentrated gave 1.2 g. IV.HSCN, m. 168-9°. IV (0.5 g.) in 5 ml. C₅-H₅N and 0.44 g. BzCl refluxed 3 hrs. and the product concentrated gave 0.37 g. 1-(4-quinolyl)-2-(benzoyl)hydrazine, m. 129.5-30.5°. IV (0.66 g.) in 5 ml. EtOH and 0.42 g. AcCH₂COMe refluxed 1 hr., the EtOH removed and the residue in 10% NaOH extracted with CHCl₃ gave 0.66 g. 1-(4quinolyl)-3,5-dimethylpyrrazole, b₄ 180-1°; picrate m. 198° (MeOH).

Yakugaku Zasshi published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C11H9ClN2O, Synthetic Route of 18437-58-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Li, Yan published the artcilePalladium-catalyzed cross-coupling of benzyltitanium(IV) reagents with aryl fluorides, Name: 4-Fluoropicolinonitrile, the publication is Monatshefte fuer Chemie (2022), 153(2), 193-199, database is CAplus.

The first palladium-catalyzed cross-coupling between benzyltitanium(IV) reagents with aryl fluorides is reported. A variety of diarylmethanes can be prepared in good to excellent yields by the catalyst system of PdCl₂(dppf)₂ associated with 1-[2-(di-tert-butylphosphanyl)phenyl]-4-methoxypiperidine. This reaction offered a highly efficient approach to diarylmethanes that are commonly found in life-changing drug mols.

Monatshefte fuer Chemie published new progress about 847225-56-3. 847225-56-3 belongs to pyridine-derivatives, auxiliary class Pyridine,Fluoride,Nitrile, name is 4-Fluoropicolinonitrile, and the molecular formula is C6H3FN2, Name: 4-Fluoropicolinonitrile.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Wolkenberg, Scott E. published the artcileDesign, synthesis, and evaluation of novel 3,6-diaryl-4-aminoalkoxyquinolines as selective agonists of somatostatin receptor subtype 2, Recommanded Product: (6-Hydroxypyridin-3-yl)boronic acid, the publication is Journal of Medicinal Chemistry (2011), 54(7), 2351-2358, database is CAplus and MEDLINE.

Agonists of somatostatin receptor subtype 2 (sst₂) have been proposed as therapeutics for the treatment of proliferative diabetic retinopathy and exudative age-related macular degeneration. An HTS screen identified 2-quinolones as weak agonists of sst₂, and these were optimized to provide small mols. with sst₂ binding and functional potency comparable to peptide agonists. Agonist I was shown to inhibit rat growth hormone secretion following systemic administration and to inhibit ocular neovascular lesion formation after local administration.

Journal of Medicinal Chemistry published new progress about 903899-13-8. 903899-13-8 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Alcohol,Boronic Acids,Boronic acid and ester, name is (6-Hydroxypyridin-3-yl)boronic acid, and the molecular formula is C3H5BN2O2, Recommanded Product: (6-Hydroxypyridin-3-yl)boronic acid.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Yuan, Chunling published the artcileCu(II)-catalyzed homocouplings of (hetero)arylboronic acids with the assistance of 2-O-methyl-D-glucopyranose, COA of Formula: C5H6BNO2, the publication is Molecules (2019), 24(20), 3678pp., database is CAplus and MEDLINE.

This is the first report of a natural ligand improving the copper-catalyzed homocouplings of (hetero)arylboronic acids. Various important synthetic biaryl intermediates in organic synthesis could be assembled via this method. To gain insight into this reaction, in-situ React IR technol. was used to confirm the effectivity of this catalyst system. This protocol provides important biaryl compounds in high yields within a short time.

Molecules published new progress about 197958-29-5. 197958-29-5 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester, name is 2-Pyridinylboronic acid, and the molecular formula is C6H16OSi, COA of Formula: C5H6BNO2.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Wang, JiaoYang published the artcileComputational study on C-B homolytic bond dissociation enthalpies of organoboron compounds, Application of 2-Pyridinylboronic acid, the publication is New Journal of Chemistry (2017), 41(3), 1346-1362, database is CAplus.

Based on many transition-metal-catalyzed Suzuki-Miyaura cross-coupling reactions of organoboron compounds in which C-B cleavages are involved, it is meaningful to understand one of the thermodn. properties of the C-B bond, the strength of the C-B bond, which can be measured using homolytic bond dissociation enthalpies (BDEs). To this end, we first calculated 64 C-B BDEs of organoboron compounds by theor. methods including composite high-level ab initio methods of G3, G4, G3B3, CBS-Q, CBS-QB3, and CBS-4M and 34 d. functional theory (DFT) methods. The results show that it is reasonable and credible to regard the average values of six composite high-level methods as the standard C-B BDE values. By comparing the DFT methods, it is found that the M06-HF method provides the most accurate results and the root mean square error (RMSE) is the smallest of 6.4 kJ mol^-1. Therefore, the C-B BDEs including C(sp)-B, C(sp²)-B and C(sp³)-B of organoboron compounds such as boronic acids, trifluoroborate salts, boronate esters, etc. as well as the substituent effects were investigated by using the M06-HF method. The results indicated that the different substituents including electron-donating groups (EDGs), electron-withdrawing groups (EWGs) and conjugated effect groups (CEGs) exhibit different effects on different types of C-B BDEs. Moreover, the natural bond orbital (NBO) anal. was performed in order to further disclose the essence of BDE change patterns.

New Journal of Chemistry published new progress about 197958-29-5. 197958-29-5 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester, name is 2-Pyridinylboronic acid, and the molecular formula is C15H20O6, Application of 2-Pyridinylboronic acid.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Wu, De-Zhi published the artcileAn efficient method for the construction of 2-Aminothiazolo[5,4-c]pyridines via K₃[Fe(CN)₆] oxidized SP² C-H Functionalization, Computed Properties of 18437-58-6, the publication is Tetrahedron (2016), 72(52), 8610-8616, database is CAplus.

A practical approach to synthesize 2-aminothiazolo[5,4-c]pyridines from simple asym. pyridylthioureas was achieved by utilizing K₃[Fe(CN)₆] as the oxidant [e.g., I → II (97%)]. These reactions went through an intramol. oxidation and finally led to the formation of C-S bond. Furthermore, the possible oxidative cyclization mechanism was also explored by the addition of radical scavengers, which showed that the oxidative cyclization was promoted via a free radical mechanism.

Tetrahedron published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C7H16Cl2Si, Computed Properties of 18437-58-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

He, Dian published the artcileDesign, Synthesis and Activity Evaluation of N-(pyridin-4-yl) Salicylamides as Antimycobacterial Agents, Computed Properties of 18437-58-6, the publication is Asian Journal of Chemistry (2014), 26(21), 7269-7275, 7 pp., database is CAplus.

A series of N-(pyridin-4-yl) salicylamides derivatives I (R¹ = H, Cl, CH₃; R² = R⁴ = H, Cl; R³ = H, Cl, CF₃; R⁵ = H, OCH₃; R⁶ = H, Cl, Br, CF₃) were prepared through acylation of the corresponding acetylsalicyloyl chlorides with substituted 4-aminopyridines. The compounds I were evaluated in vitro for antimycobacterial activities against Mycobacterium tuberculosis (TB) and Mycobacterium avium (A) by the min. inhibitory concentrations (MIC) values. Eight of the compounds I exhibited lower MIC against Mycobacterium avium than the one of isoniazide, meanwhile, four of the compounds I exhibited good anti-TB activity compared to isoniazide. Antimycobacterial activities of compounds I were influenced by the balance between hydrophobicity and electron withdrawing substituent effects on the Ph and pyridine ring.

Asian Journal of Chemistry published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C6H8N2, Computed Properties of 18437-58-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Yang, Wenqing published the artcileDesign, Synthesis, Antifungal and Antibacterial Activities of N-phenyl and N-pyridinyl-5-(trifluoromethyl)-pyrazole-4-carboxamide Derivatives, Recommanded Product: 4-Amino-2-picoline, the publication is Journal of Heterocyclic Chemistry (2018), 55(10), 2261-2269, database is CAplus.

A series of N-Ph and N-pyridinyl-5-(trifluoromethyl)-pyrazole carboxamides, compounds I [R = Ph, 2-pyridinyl, 2-fluoro-4-pyridinyl, etc.] were designed and synthesized. Bioassay results indicated that antifungal and antibacterial activities of title compounds could be obviously improved by placing trifluoromethyl on the 5-position of the pyrazole ring and substituted 4-pyridinyl at the amine side of the amide bond. The EC₅₀ values of compound I [R = 4-pyridinyl] against Gibberella zeae, Cytospora mandshurica, and Fusarium oxysporum were 14.7, 21.1, and 32.7 μg/mL, resp., better than hymexazol (30.2, 47.3, and 42.5 μg/mL) and carboxin (34.2, >200, and >200 μg/mL). And the EC₅₀ values of compounds I [R = 2-fluoro-4-pyridinyl, 2,6-dichloro-4-pyridinyl, 3,5-dichloro-4-pyridinyl, 6-methyl-2-pyridinyl, 2-methylphenyl, 2-fluorophenyl, 4-chlorophenyl and 4-methoxyphenyl] against rice bacterial leaf blight were 17.0, 21.8, 21.9, 18.6, 16.8, 25.9, 9.4, and 24.4 μg/mL, resp., much better than bismerthiazol (70.5 μg/mL).

Journal of Heterocyclic Chemistry published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C9H21NO3, Recommanded Product: 4-Amino-2-picoline.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Guo, Shuangxi published the artcileAg/C nanoparticles catalyzed aerobic oxidation of diaryl and aryl(hetero)methylenes into ketones, Synthetic Route of 197958-29-5, the publication is Nano Research (2017), 10(9), 3261-3267, database is CAplus.

The aerobic oxidation of diaryl and aryl(hetero)methylenes into ketones, catalyzed by Ag/C nanoparticles under mild conditions, was successfully developed. This method features a wide scope of substrates, good yields, and uncomplicated recycling of the catalyst.

Nano Research published new progress about 197958-29-5. 197958-29-5 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester, name is 2-Pyridinylboronic acid, and the molecular formula is C5H6BNO2, Synthetic Route of 197958-29-5.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Cheng, Kai published the artcileSilver-catalyzed decarboxylative acylation of arylglyoxylic acids with arylboronic acids, Quality Control of 197958-29-5, the publication is RSC Advances (2014), 4(89), 48698-48702, database is CAplus.

The silver-catalyzed coupling of arylboronic acids with arylglyoxylic acids was found to be an extremely efficient route for the synthesis of unsym. diaryl ketones. It was conducted on a gram scale under mild and open-flask conditions with good functional group compatibility, avoiding the addition of expensive and/or toxic metals.

RSC Advances published new progress about 197958-29-5. 197958-29-5 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester, name is 2-Pyridinylboronic acid, and the molecular formula is C5H6BNO2, Quality Control of 197958-29-5.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem