Tag: M.W=200-250

Kiselyov, Alexander S. published the artcileReaction of N-fluoropyridinium salts with Wittig reagents: a novel and convenient approach to symmetric trans-olefins, Category: pyridine-derivatives, the publication is Tetrahedron Letters (1994), 35(48), 8951-4, database is CAplus.

N-fluoropyridinium salts react with Wittig reagents containing electron-withdrawing groups to give olefins in 47-83% yield. The mechanism of this conversion is believed to involve single-electron transfer from Wittig reagent to N-fluoropyridinium cation.

Tetrahedron Letters 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 C6H5F4NO3S, Category: pyridine-derivatives.

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

Xin, Minhang published the artcileSynthesis and biological evaluation of novel 7-substituted 3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amines as potent Bruton’s tyrosine kinase (BTK) inhibitors, COA of Formula: C10H18BNO4, the publication is Bioorganic & Medicinal Chemistry (2015), 23(19), 6250-6257, database is CAplus and MEDLINE.

A series of novel 7-substituted 3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amines I [R¹ = piperidin-3-yl, piperidin-4-yl, 1,2,3,6-tetrahydropyridin-4-yl, etc.] as potent BTK inhibitors were designed, synthesized and evaluated. These thieno[3,2-c]pyridin-4-amine derivatives displayed variant inhibitory activities against BTK in vitro. Among these, 7-pyrazol-4-yl substituted 3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amine subseries showed high BTK inhibition and several compounds displayed superior BTK inhibitory activity. Comprehensive SAR was disclosed and compound I [R¹ = 1-morpholinoethanoe-2-yl] showed excellent potency (IC₅₀ = 11.8 nM), outstanding hydrophilicity (A log P = 3.53), and relatively good kinase selectivity, being a promising lead for further evaluation.

Bioorganic & Medicinal Chemistry published new progress about 844501-00-4. 844501-00-4 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Amide,Boronic Acids,Boronic acid and ester, name is (1-(tert-Butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)boronic acid, and the molecular formula is C9H6N2O2, COA of Formula: C10H18BNO4.

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

Ren, Hailong published the artcileCobalt-Catalyzed Regioselective Borylation of Arenes: N-Heterocyclic Silylene as an Electron Donor in the Metal-Mediated Activation of C-H Bonds, Name: 2,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, the publication is Chemistry – A European Journal (2017), 23(24), 5663-5667, database is CAplus and MEDLINE.

C-H Borylation of arenes has been a subject of great interest recently because of its atom-economy and the wide applicability of borylated products in value-added synthesis. A new bis(silylene)cobalt(II) complex bearing a bis(N-heterocyclic silylene)-pyridine pincer ligand (SiNSi) has been synthesized and structurally characterized. It enabled the regioselective catalytic C-H borylation of pyridines, furans, and fluorinated arenes. Notably, it exhibited complementary regioselectivity for the borylation of fluorinated arenes compared to previously known catalytic systems, demonstrating that N-heterocyclic silylene donors have enormous potential in metal-catalyzed catalytic applications.

Chemistry – A European Journal published new progress about 741709-65-9. 741709-65-9 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Pyridine,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, and the molecular formula is C13H20BNO2, Name: 2,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine.

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

Liu, Xuemei published the artcileEffect of halogenated substituents on the metabolism and estrogenic effects of the equine estrogen, equilenin, Application In Synthesis of 107263-95-6, the publication is Chemical Research in Toxicology (2003), 16(6), 741-749, database is CAplus and MEDLINE.

Estrogen replacement therapy has been correlated with an increased risk for developing breast and endometrial cancers. One potential mechanism of estrogen carcinogenesis involves metabolism of estrogens to 2- and 4-hydroxylated catechols, which are further oxidized to electrophilic/redox active o-quinones that have the potential to both initiate and promote the carcinogenic process. Previously, the authors showed that the equine estrogens, equilin and equilenin, which are major components of the estrogen replacement formulation Premarin (Wyeth-Ayerst), are primarily metabolized to the catechol, 4-hydroxyequilenin. This catechol was found to autoxidize to an o-quinone causing oxidation and alkylation of DNA in vitro and in vivo. To block catechol formation from equilenin, 4-halogenated equilenin derivatives were synthesized. These derivatives were tested for their ability to bind to the estrogen receptor, induce estrogen sensitive genes, and their potential to form catechol metabolites. The authors found that the 4-fluoro derivatives were more estrogenic than the 4-chloro and 4-bromo derivatives as demonstrated by a higher binding affinity for estrogen receptors α and β, an enhanced induction of alk. phosphatase activity in Ishikawa cells, pS2 expression in S30 cells, and PR expression in Ishikawa cells. Incubation of these compounds with tyrosinase in the presence of GSH showed that the halogenated equilenin compounds formed less catechol GSH conjugates than the parent compounds, equilenin and 17β-hydroxyequilenin. In addition, these halogenated compounds showed less cytotoxicity in the presence of tyrosinase than the parent compounds in S30 cells. Also, as stated above, the 4-fluoro derivatives showed similar estrogenic effects as compared with parent compounds; however, they were less toxic in S30 cells as compared to equilenin and 17β-equilenin. Because 17β-hydroxy-4-halogenated equilenin derivatives showed higher estrogenic effects than the halogenated equilenin derivatives in vitro, the authors studied the relative ability of the 17β-hydroxy-4-halogenated equilenin derivatives to induce estrogenic effects in the ovariectomized rat model. The 4-fluoro derivative showed higher activity than 4-chloro and 4-bromo derivatives as demonstrated by inducing higher vaginal cellular differentiation, uterine growth, and mammary gland branching. However, 17β-hydroxy-4-fluoroequilenin showed a lower estrogenic activity than 17β-hydroxyequilenin and estradiol, which could be due to alternative pharmacokinetic properties for these compounds These data suggest that the 4-fluoroequilenin derivatives have promise as alternatives to traditional estrogen replacement therapy due to their similar estrogenic properties with less overall toxicity.

Chemical Research in Toxicology 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 C6H5F4NO3S, Application In Synthesis of 107263-95-6.

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

Alshreimi, Abdullah S. published the artcileSynthesis of Spirocyclic 1-Pyrrolines from Nitrones and Arynes through a Dearomative [3,3′]-Sigmatropic Rearrangement, Category: pyridine-derivatives, the publication is Angewandte Chemie, International Edition (2020), 59(35), 15244-15248, database is CAplus and MEDLINE.

A dearomative [3,3′]-sigmatropic rearrangement that converts N-alkenylbenzisoxazolines into spirocyclic pyrroline cyclohexadienones, e.g., I, has been developed by using the dipolar cycloaddition of an N-alkenylnitrone and an aryne to access these unusual transient rearrangement precursors. This cascade reaction affords spirocyclic pyrrolines that are inaccessible through dipolar cycloadditions of exocyclic cyclohexenones and provides a fundamentally new approach to novel spirocyclic pyrroline and pyrrolidine motifs that are common scaffolds in biol.-active mols. Diastereoselective functionalization processes have also been explored to demonstrate the divergent synthetic utility of the unsaturated spirocyclic products.

Angewandte Chemie, International Edition published new progress about 844501-00-4. 844501-00-4 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Amide,Boronic Acids,Boronic acid and ester, name is (1-(tert-Butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)boronic acid, and the molecular formula is C10H18BNO4, Category: pyridine-derivatives.

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

Liao, Lihao published the artcileSelenium-π-Acid Catalyzed Oxidative Functionalization of Alkynes: Facile Access to Ynones and Multisubstituted Oxazoles, Application In Synthesis of 107263-95-6, the publication is ACS Catalysis (2018), 8(7), 6745-6750, database is CAplus.

In the presence of di-Ph diselenide, N-fluoropyridinium triflates, and water, propargyl phosphonates such as PhCCCH₂P(:O)(OEt)₂ and β,γ-alkynoates underwent regioselective oxidation to yield γ-ketoalkynyl phosphonates such as PhCOCCP(:O)(OEt)₂ and γ-keto-α,β-alkynoates. Ynamides such as PhCCN(CH₂Ph)R (R = MeSO₂, PhSO₂, 4-MeC₆H₄SO₂, 4-O₂NC₆H₄) underwent regioselective oxidative cycloadditions with acetonitrile or butanenitrile mediated by Selectfluor in the presence of di-Ph selenide to yield aminooxazoles such as I (R = MeSO₂, PhSO₂, 4-MeC₆H₄SO₂, 4-O₂NC₆H₄). N-Propargylamides underwent oxidative cyclization in the presence of di-Ph diselenide and mediated by Selectfluor to give 2-substituted-5-oxazolecarboxaldehydes. In all cases, the reactions are likely to involve the reactions of cationic phenylselenium species with alkynes to generate vinylselenium cations. The mechanism of the reactions were studied; vinyl selenides were prepared by reactions of phenylselenium triflate with propargyl phosphonates and ynamides and shown to yield the observed ketone and oxazole products upon elimination, while isotopic labeling experiments were undertaken to determine the fate of added water.

ACS Catalysis 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 C6H5F4NO3S, Application In Synthesis of 107263-95-6.

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

Zhang, Yu published the artcileA new tetraphosphine and its application in Pd-catalyzed Suzuki cross-coupling reaction, Recommanded Product: 5-Nitro-2-phenylpyridine, the publication is Youji Huaxue (2012), 32(4), 790-793, database is CAplus.

A new tetraphosphine, N,N,N’,N’-tetra(diphenylphosphinomethyl)-cyclohexane-1,2-diamine has been designed and synthesized from the com. available cyclohexane-1,2-diamine as starting material. This tetraphosphine in combination with [Pd(η³-C₃H₅)Cl]₂ is a very efficient catalyst for Suzuki cross-coupling reaction. Various aryl and heteroaryl chlorides or bromides could be successfully transformed to the desired products in up to 99% yield with 0.1 mol% catalyst loading.

Youji Huaxue published new progress about 89076-64-2. 89076-64-2 belongs to pyridine-derivatives, auxiliary class Pyridine,Nitro Compound,Benzene, name is 5-Nitro-2-phenylpyridine, and the molecular formula is C7H7ClN2S, Recommanded Product: 5-Nitro-2-phenylpyridine.

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

Liu, Qilun published the artcileAbnormal Mesoionic Carbene Silver Complex: Synthesis, Reactivity, and Mechanistic Insight on Oxidative Fluorination, Recommanded Product: 1-Fluoropyridiniumtriflate, the publication is ACS Catalysis (2015), 5(11), 6732-6737, database is CAplus.

A silver-catalyzed intramol. amination of alkynyl-imine substrates has been extensively studied to build various isoquinoline derivatives efficiently. However, most of these transformations are limited to hydroamination, and the related oxidative reaction is quite rare. Importantly, the mechanistic details are still unknown, which retarded further progress in the field. In this work, a novel abnormal mesoionic carbene silver complex (MIC)_nAg(I) was isolated and fully characterized as the key intermediate. Further investigation on the oxidative transformation of the silver complex reveals that successful oxidative halogenation could be achieved with NXS (X = Cl, Br, and I), as well as F⁺ reagent. Surprisingly, the fluorination reaction occurred in the presence of both strong (SelectFluor) and weak (NFSI) fluorinating reagents, although the F-Py-type reagent, whose oxidative potential lies between, is ineffective. Further mechanistic studies disclosed that (1) from kinetic data, the (MIC)Ag(I) complex was proved to be the reactive intermediate in the fluorination reaction, and pyridyl-oxazoline (Pyox) ligand could significantly improve this transformation; (2) from DFT calculation results, two different mechanistic pathways were suggested to be involved, a metathesis process in the case of NFSI promoted by the chelation of sulfonyl group toward the silver center and a redox process in the case of SelectFluor due to its strong oxidative potential.

ACS Catalysis 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 C6H5F4NO3S, Recommanded Product: 1-Fluoropyridiniumtriflate.

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

Baba, Daisuke published the artcileElectrolytic partial fluorination of organic compounds. Part 62. Highly diastereoselective anodic fluorination of chiral 1,3-oxathiolan-5-ones derived from camphorsulfonamides, Quality Control of 107263-95-6, the publication is Journal of Fluorine Chemistry (2003), 121(1), 93-96, database is CAplus.

Anodic fluorination of chiral 1,3-oxathiolan-5-ones, derived from camphorsulfonamide and thioglycolic acid, was carried out under various conditions. When dimethoxyethane (DME) containing Et₄NF·4HF was used, the corresponding monofluorinated products were obtained in good yield as a single diastereomer. Chem. fluorination was also attempted using N-fluoropyridinium salts; however, fluorination did not proceed at all. The anodic fluorination of (+)-(1R,2R,4R)-7,7-dimethyl-N,N-bis(1-methylethyl)-5′-oxo-spiro[bicyclo[2.2.1]heptane-2,2′-[1,3]oxathiolane]-1-methanesulfonamide gave (+)-(1R,2R,4R,4′S)-4′-Fluoro-7,7-dimethyl-N,N-bis(1-methylethyl)-5′-oxo-spiro[bicyclo[2.2.1]heptane-2,2′-[1,3]oxathiolane]-1-methanesulfonamide (I). Crystal and mol. structures of I were reported.

Journal of Fluorine Chemistry 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 C6H5F4NO3S, Quality Control of 107263-95-6.

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

Lou, Shao-Jie published the artcilePd(OAc)₂-catalyzed regioselective aromatic C-H bond fluorination, Category: pyridine-derivatives, the publication is Chemical Communications (Cambridge, United Kingdom) (2013), 49(55), 6218-6220, database is CAplus and MEDLINE.

A novel Pd(OAc)₂-NFSI-TFA system was developed for the highly selective ortho-monofluorination directed by diverse aryl-N-heterocyclic directing groups e.g., quinoxaline, pyrazole, benzo[d]oxazole, and pyrazine derivatives A Pd(ii/iv) catalytic cycle was proposed based on the ESI-MS/MS studies.

Chemical Communications (Cambridge, United Kingdom) 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 C6H5F4NO3S, Category: pyridine-derivatives.

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