Month: December 2022

Yokoyama, Yasuo published the artcileThe development of a novel synthetic method for cyanofluoroamides using a cobaltadithiolene complex, Recommanded Product: 1-Fluoropyridiniumtriflate, the publication is Synthesis (2004), 701-705, database is CAplus.

N,N-Di-Et 2-cyano-2-fluoro-2-(phenylthio)acetamide reacted with germyl anion species to give the corresponding enolate. When this enolate was treated with an unsaturated organic halide, in the presence of a catalytic amount of cobaltadithiolene I, II was obtained in good yield. Interestingly, in the absence of I, no target product was obtained. This reaction proceeded smoothly under mild reaction conditions and only cyanofluoroamide was obtained.

Synthesis published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C17H14F3N3O2S, Recommanded Product: 1-Fluoropyridiniumtriflate.

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

Ochiai, Eiji published the artcilePolarization of aromatic heterocyclic compounds. LXVI. Reduction of 4-nitro-2-picoline 1-oxide, Safety of 4-Amino-2-picoline, the publication is Yakugaku Zasshi (1947), 158-60, database is CAplus.

Reduction of 4-nitro-2-picoline 1-oxide (I) indicated that it also had certain peculiarities which were observed in the reduction of 4-nitropyridine 1-oxide (C.A. 45, 5151h). Catalytic reduction of I in 10% HCl with 60% Pd-charcoal gave a HCl salt of 4-amino-2-picoline 1-oxide (II), needles, m. 189-91°. Further reduction of the II.HCl in AcOH-Ac₂O with 60% Pd-charcoal gave 4-amino-2-picoline (III), slightly hygroscopic cubic crystals, m. 95°; picrate, m. 193°. Catalytic reduction of I to III did not proceed well in HCl and EtOH. Reduction of I in a mixture of H₂S-saturated NH₄OH and EtOH gave 4,4′-azo-2-picoline 1,1′-dioxide (IV), red needles, m. 224-5°. Reduction of I in 10% NaOH solution with NaNO₂ at about 45° gave IV and a small amount of recovered I. MeOH as a solvent gave 4-methoxy-2-picoline 1-oxide, rhomboprisms, m. 78-80°, and no azo compound was formed. Reduction of I in glacial AcOH, EtOH, and H₂O with Zn dust also gave IV, while reduction in glacial AcOH with Zn gave 4,4′-azoxy-2-picoline 1,1′-dioxide (V), orange-red crystals, m. 220-1°, and a small amount of recovered I. Reduction in EtOH-glacial AcOH with Zn gave chiefly V with a small amount of IV, and reduction in H₂O alone in a sealed tube gave V with recovery of I. Reduction in NaOH solution gave III. Since this reduction, when carried out on a water bath about 1 hr. gave only IV with recovery of I, the reduction was assumed to proceed via the azo compound Reduction of I in HCl with SnCl₂ gave IV, as well as III, while reduction in EtOH with Na₂S₂O₄ also gave III.

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 C6H8N2, Safety of 4-Amino-2-picoline.

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

Ochiai, Eiji published the artcilePolarization of aromatic heterocyclic compounds. CV. 4-Substituted derivatives of α-picoline, Application of 4-Amino-2-picoline, the publication is Pharmaceutical Bulletin (1954), 147-9, database is CAplus.

cf. C.A. 48, 10746c. PCl₃ (10 g.) added portionwise with ice cooling to 10 g. 4-nitro-α-picoline N-oxide in 200 ml. of CHCl₃, the mixture warmed at 50° for 10 min., cooled, poured onto ice, neutralized with Na₂CO₃, extracted with CHCl₃, dried over Na₂SO₄, and evaporated gave 7 g. 4-nitro-α-picoline (I), m. 42-5° (from petr. ether). I (1 g.) dissolved in MeOH and reduced over Pd-C gave 4-amino-α-picoline, purified through the picrate, m. 193°. 4-Bromo-α-picoline (II) (picrate, m. 184-5°) was prepared by 4 methods: (1) I (1 g.) heated at 150-70° for 8 hrs. with 5 g. 48% HBr, the mixture evaporated under reduced pressure, alkalinized with Na₂CO₃, extracted with Et₂O, dried over Na₂SO₄ and evaporated gave 0.2 g. II, an oily residue, which was converted to the picrate. (2) I (5 g.), 26 g. of (H₂N)₂CO and 30 ml. 48% HBr refluxed 7 hrs., diluted with H₂O, alkalinized with Na₂CO₃, steam distilled, the distillate saturated with NaCl, extracted with Et₂O, the Et₂O extract dried over Na₂SO₄, the Et₂O removed, and the residue distilled gave 1.2 g. II, b₅ 47-56°. (3) I (3 g.) and 5 ml. AcBr heated 6 hrs. on a water bath (a red color developed), the mixture evaporated in vacuo, diluted with H₂O, alkalinized with Na₂CO₃, and extracted with Et₂O, and the extract distilled gave 1.2 g. II. (4) 4-Hydroxy-α-picoline N-oxide (10 g.) in 60 ml. CHCl₃ cooled and treated portionwise with 25 g. PBr₃ in 20 ml. CHCl₃; after the reaction subsided the mixture was refluxed 6 hrs. on a water bath and a sirupy mass precipitated The CHCl₃ layer extracted with H₂O, the sirupy residue treated with 200 ml. ice water, the aqueous solutions mixed, alkalinized with Na₂CO₃, steam distilled, the distillate saturated with NaCl, extracted with Et₂O, and the extract distilled in vacuo gave 7.8 g. II. CuCN (dried at 110° for 36 hrs.) (2.5 g.) added to 4.5 g. II, the mixture gradually heated to 150-60° when the mixture melted with darkening, the temperature raised to 180° then cooled to 120°, 1 g. CuCN added, the mixture heated 0.25 hrs. at 170-80° and distilled gave 2.2 g. 4-cyano-α-picoline (III), b_11-15 about 75°, m. 45.5-6.5° (from petr. ether); picrate, decompose 163-4° (from EtOH). III (1.5 g.) reduced over Pd-C in acid solution gave 1.6 g. 4-amino-αpicoline, decompose 274° (from MeOH); picrate, m. 195-6° (from MeOH); benzoate, m. 81-3° (from benzene).

Pharmaceutical Bulletin 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, Application of 4-Amino-2-picoline.

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

Devarajan, Nainamalai published the artcileCopper-catalyzed oxidative coupling of arylboronic acids with aryl carboxylic acids: Cu₃(BTC)₂ MOF as a sustainable catalyst to access aryl esters, Application In Synthesis of 197958-29-5, the publication is Organic Chemistry Frontiers (2018), 5(15), 2322-2331, database is CAplus.

A convenient and sustainable method was demonstrated for the oxidative coupling of arylboronic acids with aryl carboxylic acids via C-O cross-coupling reaction catalyzed by the unsaturated coordination sites of copper present in the Cu₃(BTC)₂ MOF. Cu₃(BTC)₂ was employed in a MOF-based catalysis reaction with high efficiency and high chemoselectivity without the use of any external oxidants, ligands or additives. The present methodol. avoided stoichiometric reagents and special reaction conditions and showed excellent functional group tolerance with decent to excellent yields of aryl esters R¹C(O)OR² [R¹ = Ph, 4-ClC₆H₄, 2-naphthyl, etc.; R² = Me, 3-MeOC₆H₄, 4-O₂NC₆H₄, etc.]. The catalyst was found to exhibit high stability and reusability, without loss in activity even after several cycles, which was evident from the FT-IR, PXRD and SEM characterizations of the reused catalyst.

Organic Chemistry Frontiers 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, Application In Synthesis of 197958-29-5.

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

Chang, Sheng published the artcilePd-Catalyzed desulfitative reaction of aryltrifluoroborates with sodium arenesulfinates in water, Application of 2-Pyridinylboronic acid, the publication is Applied Organometallic Chemistry (2018), 32(1), n/a, database is CAplus.

An efficient procedure for the synthesis of biaryls was catalyzed by Pd(CH₃CN)₄(BF₄)₂ is reported. This Pd-catalyzed cross-coupling reaction of aryltrifluoroborates with sodium arenesulfinates was developed under mild and environmentally benign conditions, in water without any ligand or additive. The reaction gave a range of structurally diverse unsym. bi-aryl mols. with excellent yields, in which the byproduct was sulfur dioxide. It is worth noting that this protocol is also applicable to many heterocyclic aromatics such as thiophene, furan, pyridine, quinoline, isoquinoline and indole.

Applied Organometallic 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 C5H6BNO2, Application of 2-Pyridinylboronic acid.

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

Patel, Paresma R. published the artcileIn vitro evaluation of imidazo[4,5-c]quinolin-2-ones as gametocytocidal antimalarial agents, Synthetic Route of 903899-13-8, the publication is Bioorganic & Medicinal Chemistry Letters (2016), 26(12), 2907-2911, database is CAplus and MEDLINE.

Novel imidazo[4,5-c]quinolin-2-ones, such as I, were synthesized and evaluated in asexual blood stage and late stage gametocyte assays of Plasmodium falciparum, a major causative agent of malaria. The design of these compounds is based on a recently identified lead compound from a high throughput screen. A concise synthesis was developed that allowed for generation of analogs with substitution around both the quinoline and imidazolidinone rings. Through structure-activity relationship studies, a number of potent compounds were identified that possessed excellent antimalarial activity against both the asexual and sexual stages with minimal cytotoxicity in mammalian cells. This is the first Letter describing SAR and gametocytocidal activity of imidazo[4,5-c]quinolin-2-ones, a new lead series for malaria treatment and prevention.

Bioorganic & Medicinal Chemistry Letters 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 C5H6BNO3, Synthetic Route of 903899-13-8.

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

Li, Hao published the artcileEfficient Synthesis of 1,9-Substituted Benzo[h][1,6]naphthyridin-2(1H)-ones and Evaluation of their Plasmodium falciparum Gametocytocidal Activities, Recommanded Product: (6-Hydroxypyridin-3-yl)boronic acid, the publication is ACS Combinatorial Science (2017), 19(12), 748-754, database is CAplus and MEDLINE.

A novel three-component, two-step, 1-pot nucleophilic aromatic substitution (S_NAr)-intramol. cyclization-Suzuki coupling reaction was developed for the synthesis of benzo[h][1,6]naphthyridin-2(1H)-ones (Torins). On the basis of the new efficiently convergent synthetic route, a library of Torin 2 analogs was synthesized. The antimalarial activities of these compounds were evaluated against asexual parasites using a growth inhibition assay and gametocytes using a viability assay.

ACS Combinatorial Science 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 C5H6BNO3, Recommanded Product: (6-Hydroxypyridin-3-yl)boronic acid.

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

Hou, Chuanfu published the artcileVisible-Light-Induced Decarboxylative Acylation of Pyridine N-Oxides with α-Oxocarboxylic Acids Using Fluorescein Dimethylammonium as a Photocatalyst, HPLC of Formula: 91-02-1, the publication is Advanced Synthesis & Catalysis (2021), 363(11), 2806-2812, database is CAplus.

The development of a visible-light-induced catalytic system achieved the decarboxylative acylation of pyridine N-oxides with α-oxocarboxylic acids, at room temperature and using the organic dye fluorescein dimethylammonium as a new type of photocatalyst was reported. A series of 2-arylacylpyridine N-oxides were selectively synthesized in moderate to good yields by controlling the polarity of the reaction solvent. The developed strategy was successfully applied in the synthesis of an important intermediate of the drug, acrivastine, on a gram scale. Notably, this is the first time that fluorescein dimethylammonium was used to catalyzed the Minisci-type C-H decarboxylative acylation reaction. The mechanism of decarboxylative acylation was studied by capturing adducts of acyl radicals and 1,1-diphenylethylene confirmed a radical mechanism. The disclosed catalytic system provided a green synthetic strategy for decarboxylative acylation without the use of addnl. oxidants or metal catalysts.

Advanced Synthesis & Catalysis published new progress about 91-02-1. 91-02-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene,Ketone, name is Phenyl(pyridin-2-yl)methanone, and the molecular formula is C12H9NO, HPLC of Formula: 91-02-1.

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

Shang, Ming published the artcileCu(II)-Mediated C-H Amidation and Amination of Arenes: Exceptional Compatibility with Heterocycles, Computed Properties of 18437-58-6, the publication is Journal of the American Chemical Society (2014), 136(9), 3354-3357, database is CAplus and MEDLINE.

A Cu(OAc)₂-mediated C-H amidation and amination of arenes and heteroarenes has been developed using a readily removable directing group. A wide range of sulfonamides, amides, and anilines function as amine donors in this reaction. Heterocycles present in both reactants are tolerated, making this a broadly applicable method for the synthesis of a family of inhibitors including 2-benzamidobenzoic acids and N-phenylaminobenzoates.

Journal of the American Chemical Society 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 C2H3N3, Computed Properties of 18437-58-6.

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

Plamthottam, Sheba published the artcileActivity and electrochemical properties: iron complexes of the anticancer drug triapine and its analogs, Name: 2-Bromopyridin-3-amine, the publication is JBIC, Journal of Biological Inorganic Chemistry (2019), 24(5), 621-632, database is CAplus and MEDLINE.

Abstract: Triapine (3-AP), is an iron-binding ligand and anticancer drug that is an inhibitor of human ribonucleotide reductase (RNR). Inhibition of RNR by 3-AP results in the depletion of dNTP precursors of DNA, thereby selectively starving fast-replicating cancer cells of nucleotides for survival. The redox-active form of 3-AP directly responsible for inhibition of RNR is the Fe(II)(3-AP)₂ complex. In this work, we synthesize 12 analogs of 3-AP, test their inhibition of RNR in vitro, and study the electronic properties of their iron complexes. The reduction and oxidation events of 3-AP iron complexes that are crucial for the inhibition of RNR are modeled with solution studies. We monitor the pH necessary to induce reduction in iron complexes of 3-AP analogs in a reducing environment, as well as the kinetics of oxidation in an oxidizing environment. The oxidation state of the complex is monitored using UV-Vis spectroscopy. Isoquinoline analogs of 3-AP favor the maintenance of the biol. active reduced complex and possess oxidation kinetics that allow redox cycling, consistent with their effective inhibition of RNR seen in our in vitro experiments In contrast, methylation on the thiosemicarbazone secondary amine moiety of 3-AP produces analogs that form iron complexes with much higher redox potentials, that do not redox cycle, and are inactive against RNR in vitro. Graphic abstract: The catalytic subunit of human Ribonucleotide Reductase (RNR), contains a tyrosyl radical in the enzyme active site. Fe(II) complexes of 3-AP and its analogs can quench the radical and, subsequently, inactivate RNR. The potency of RNR inhibitors is highly dependent on the redox properties of the iron complexes, which can be tuned by ligand modifications. Complexes are found to be active within a narrow redox window imposed by the cellular environment.[Figure not available: see fulltext.].

JBIC, Journal of Biological Inorganic Chemistry published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, Name: 2-Bromopyridin-3-amine.

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