Tag: M.W=200-250

Suzuki, Katsutoshi published the artcileElectrolytic Partial Fluorination of Organic Compounds.71.Highly Diastereoselective Anodic Fluorination of Sulfides Having Oxygen-Containing Heterocyclic Groups, SDS of cas: 107263-95-6, the publication is Journal of Organic Chemistry (2004), 69(4), 1276-1282, database is CAplus and MEDLINE.

Racemic and nonracemic α-fluoro-β-alkoxysulfides and (arylsulfanylfluoromethyl)dioxolanes such as I are prepared stereoselectively by electrochem. fluorination of β-alkoxysulfides and (arylsulfanylmethyl)dioxolanes such as II with Et₃N•3HF in acetonitrile. The 2-spirocyclohexyl-1,3-dioxolanemethyl sulfide II gives the desired α-fluorosulfide in 54% yield and with 80% de.; other sulfides give the desired product in in 10-77% yields and with 13-70% de. The diastereoselectivity of the electrochem. fluorination increases with decreasing Gutmann donor number of the solvent. Et₃N•3HF is the most effective fluorination electrolyte used; other amine hydrofluorides give fluorinated product in 0-8% yields and with reduced stereoselectivity. Chem. fluorination of II using Selectfluor also gives I, but in only 5% yield and in 32% de.; chem. fluorination using N-fluoropyridinium salts gives no fluorination products. Decomposition occurs upon acidic hydrolysis of I; oxidation of I to the Ph sulfone followed by acidic hydrolysis yields the nonracemic fluoroinated dihydroxysulfone III. The structure and stereochem. of dioxolanone IV is determined by X-ray crystallog.

Journal of Organic 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 C9H9ClN2, SDS of cas: 107263-95-6.

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

Umemoto, Teruo published the artcilePower- and structure-variable fluorinating agents. The N-fluoropyridinium salt system, Computed Properties of 107263-95-6, the publication is Journal of the American Chemical Society (1990), 112(23), 8563-75, database is CAplus.

The usefulness of the N-fluoropyridinium salt system as a source of fluorinating agents was examined by using substituted or unsubstituted N-fluoropyridinium triflates, N-fluoropyridinium salts possessing other counteranions, and two N-fluoropyridinium-2-sulfonates (I). Electrophilic fluorinating power varied remarkably according to the electronic nature of the ring substituents. This power increased as the electron d. of pos. N sites decreased, and this was correlated to the pK_a values of the corresponding pyridines. By virtue of this variation, it was possible to fluorinate a wide range of nucleophile substrates differing in reactivity, e.g., aromatics, carbanions, active methylene compounds, enol alkyl or silyl ethers, vinyl acetates, ketene silyl acetals, and olefins. All the reactions could be explained on the basis of a one-electron-transfer mechanism. N-Fluoropyridinium salts showed high chemoselectivity in fluorination, the extent depending on the reactive moiety. Selective 9α-fluorination of steroids was carried out with the tris(trimethylsilyl ether) of a triketo steroid. Regio- or stereoselectivity in fluorination was determined by N-fluoropyridinium salt structure. Steric bulkiness of the N-F surroundings hindered the orthofluorination of phenols and aniline derivatives, while the capacity for H bonding on the part of the counteranions prompted this process, and I underwent this fluorination exclusively or almost so. Two bulky N-fluoropyridinium triflates preferentially attacked the 6-position of the conjugated vinyl ester of a steroid from the unhindered β-direction to give a thermally unstable 6β-fluoro isomer. N-Fluoropyridinium salt systems can serve as a source of the most ideal fluorinating agents for conducting desired selective fluorination through fluorinating capacity or structural alteration.

Journal of the American Chemical Society 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 C18H35NO, Computed Properties of 107263-95-6.

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

Zhang, Xitao published the artcileTransition-Metal-Free Decarboxylative Arylation of 2-Picolinic Acids with Arenes under Air Conditions, Recommanded Product: 5-Nitro-2-phenylpyridine, the publication is Organic Letters (2018), 20(22), 7095-7099, database is CAplus and MEDLINE.

A facile, transition-metal-free, and direct decarboxylative arylation of 2-picolinic acids with simple arenes is described. The oxidative decarboxylative arylation of 2-picolinic acids with arenes proceeds readily via N-chloro carbene intermediates to afford 2-arylpyridines in satisfactory to good yields under transition-metal-free conditions. This new type of decarboxylative arylation is operationally simple and scalable and exhibits high functional-group tolerance. Various synthetically useful functional groups, such as halogen atoms, methoxycarbonyl, and nitro, remain intact during the decarboxylative arylation of 2-picolinic acids.

Organic Letters 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 C7H6FNO3, Recommanded Product: 5-Nitro-2-phenylpyridine.

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

Bew, Sean P. published the artcileOrganocatalytic Aziridine Synthesis Using F⁺ Salts, Product Details of C6H5F4NO3S, the publication is Organic Letters (2009), 11(20), 4552-4555, database is CAplus and MEDLINE.

This paper describes a unique application of the fluoronium cation (F⁺) as an organocatalyst for mediating the reaction between N-substituted imines and Et diazoacetate affording excellent yields of N-substituted aziridines. E.g., N-fluoropyridinium triflate catalyzed the reaction of (E)-N-arylimine I with Et diazoacetate to give 83% cis-aziridine II.

Organic 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, Product Details of C6H5F4NO3S.

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

Chung, Yongseog published the artcileStructural effects controlling the rate of the retro-Diels-Alder reaction in anthracene cycloadducts, Computed Properties of 107263-95-6, the publication is Journal of Organic Chemistry (1989), 54(5), 1018-32, database is CAplus.

A fairly broad study of how the structure of an anthracene cycloadduct affects the rate of its cycloreversion reaction was undertaken. Conclusions were drawn based on the rate constants for retro-Diels-Alder (rDA) reactions of a variety of anthracene-type adducts conducted in di-Ph ether. The rDA reaction of anthracene cycloadducts is influenced by diene substituents in the following ways: (1) electron-donating groups increase the reaction rate, and the accelerating effect is subject to geometric modulation for a conjugating substituent like dimethylamino; (2) electron-withdrawing groups may decrease or increase the reaction rate, although the effect is rarely large; and (3) steric acceleration is relatively small and demonstrates an unprecedented bell-shaped structure-reactivity profile. Peripheral substitution of the adduct with siloxy groups results in a significant acceleration, even though the groups are three bonds removed from the reaction site. The same reaction is influenced by dienophile substituents in the following ways: (1) electron-withdrawing groups increase the rate of the reaction; (2) strongly conjugating substituents make the reaction much faster than predicted by classical electron-withdrawing or -donating ability due to a change to polar mechanism; and (3) there is no observable steric effect.

Journal of Organic 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, Computed Properties of 107263-95-6.

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

Tohda, Yasuo published the artcileNucleophilic reaction upon electron-deficient pyridone derivatives. X. One-pot synthesis of 3-nitropyridines by ring transformation of 1-methyl-3,5-dinitro-2-pyridone with ketones or aldehydes in the presence of ammonia, Application In Synthesis of 89076-64-2, the publication is Bulletin of the Chemical Society of Japan (1990), 63(10), 2820-7, database is CAplus.

The reaction of 1-methyl-3,5-dinitro-2-pyridone (I) with aldehydes, ketones, or enamines in the presence of NH₃ gave alkyl and/or aryl-substituted 3-nitropyridine derivatives Enamines derived from ketones gave better results than the ketones themselves; enamines derived from aldehydes did not react. I reacted as an equivalent of NaO₂N:C(CHO)₂. A mechanistic pathway was discussed.

Bulletin of the Chemical Society of Japan 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 C15H15OP, Application In Synthesis of 89076-64-2.

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

Rao, Maddali L. N. published the artcileTriarylbismuthanes as Threefold Aryl-Transfer Reagents in Regioselective Cross-Coupling Reactions with Bromopyridines and Quinolines, Related Products of pyridine-derivatives, the publication is European Journal of Organic Chemistry (2014), 2014(24), 5214-5228, database is CAplus.

Cross-coupling studies using bromopyridines and bromoquinolines with triarylbismuths as threefold coupling reagents in substoichiometric amounts under Pd-catalyzed conditions are disclosed. The reactivity was high with both mono- and dibromopyridyl substrates, and mono- and bis-couplings were carried out regioselectively. A library of monoaryl and diaryl pyridines was formed in high yields. A one-pot strategy provided a simple and straightforward synthesis of both sym. and unsym. diarylpyridines. Arylations of 2-bromo- and 3-bromoquinolines were achieved with triarylbismuth reagents. This study demonstrates that triarylbismuths may be used as threefold arylating reagents for the synthesis of aryl pyridines and quinolines through couplings with bromopyridines and bromoquinolines under Pd-catalyzed conditions.

European Journal of Organic Chemistry 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 C11H8N2O2, Related Products of pyridine-derivatives.

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

Rao, Maddali L. N. published the artcileCross-coupling study of iodo/chloropyridines and 2-chloroquinoline with atom-economic triarylbismuth reagents under Pd-catalysis, Application In Synthesis of 89076-64-2, the publication is Tetrahedron (2015), 71(2), 338-349, database is CAplus.

This study describes the palladium-catalyzed couplings of iodopyridines, chloropyridines, and chloroquinoline with atom-economic BiAr₃ reagents in sub-stoichiometric loadings. Mono-arylations of iodo and chloropyridines produced arylpyridines in high yields. The couplings addressed with dihalopyridines have afforded chemo- and regioselective coupling products. Arylations of 2-chloroquinoline with different triarylbismuth reagents demonstrated fruitful coupling reactivity under the established conditions. This sumptuous study demonstrates the remarkable cross-coupling reactivity of iodo/chloropyridines and chloroquinoline with triarylbismuth reagents.

Tetrahedron 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 C11H8N2O2, Application In Synthesis of 89076-64-2.

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

Bromidge, Steven M. published the artcileBiarylcarbamoylindolines Are Novel and Selective 5-HT_2C Receptor Inverse Agonists: Identification of 5-Methyl-1-[[2-[(2-methyl-3-pyridyl)oxy]- 5-pyridyl]carbamoyl]-6-trifluoromethylindoline (SB-243213) as a Potential Antidepressant/Anxiolytic Agent, Recommanded Product: 5-Nitro-2-phenylpyridine, the publication is Journal of Medicinal Chemistry (2000), 43(6), 1123-1134, database is CAplus and MEDLINE.

The evolution, synthesis, and biol. activity of a novel series of 5-HT_2C receptor inverse agonists are reported. Biarylcarbamoylindolines have been identified with excellent 5-HT_2C affinity and selectivity over 5-HT_2A receptors. In addition, (pyridyloxypyridyl)carbamoylindolines have been discovered with addnl. selectivity over the closely related 5-HT_2B receptor. Compounds from this series are inverse agonists at the human cloned 5-HT_2C receptor, completely abolishing basal activity in a functional assay. The new series have reduced P 450 inhibitory liability compared to a previously described series of 1-(3-pyridylcarbamoyl)indolines (Bromidge et al. J. Med. Chem. 1998, 41, 1598) from which they evolved. Compounds from this series showed excellent oral activity in a rat mCPP hypolocomotion model and in animal models of anxiety. On the basis of their favorable biol. profile, SB-228357 and SB-243213 have been selected for further evaluation to determine their therapeutic potential for the treatment of CNS disorders such as depression and anxiety.

Journal of Medicinal Chemistry 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 C11H8N2O2, Recommanded Product: 5-Nitro-2-phenylpyridine.

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

Pang, Yuan-Ping published the artcileSmall molecules showing significant protection of mice against botulinum neurotoxin serotype A, COA of Formula: C6H5F4NO3S, the publication is PLoS One (2010), 5(4), No pp. given, database is CAplus and MEDLINE.

Botulinum neurotoxin serotype A (BoNTA) causes a life-threatening neuroparalytic disease known as botulism that could afflict large, unprotected populations if the toxin were employed in an act of bioterrorism. Current post-exposure therapy is limited to symptomatic treatment or passive immunization that is effective for treating infant botulism at a cost of US $45,300 per treatment regimen. Antibodies can neutralize the extracellular but not the intracellular BoNTA. Moreover, antibody production, storage, and administration in a mass casualty scenario pose logistical challenges. Alternatively, small-mol. inhibitors of BoNTA endopeptidase (BoNTAe) are sought to antagonize the extracellular or intracellular toxin. While several such mols. reportedly demonstrated efficacy in protecting cells against BoNTA, there is scant information to show that small mols. can significantly protect mammals against BoNTA. Herein the authors report the development of effective small-mols. BoNTAe inhibitors with promising in vivo pharmacokinetics. One such mol. has an in vivo half-life of 6.5 h and is devoid of obvious sign of toxicity. Pre-treatment with this mol. at 2 mg/kg protected 100% and 70% of treated mice against BoNTA at 5 times of its median-LD during the periods of 2 and 4 half-lives of the inhibitor, resp. In contrast, 40% and 0% of untreated mice survived during the resp. periods. Similar levels of protection were also observed with two other small mols. These results demonstrate that small mols. can significantly protect mice against BoNTA and support the pursuit of small-mol. antagonists as a cost-effective alternative or as an adjunct to passive immunity for treating botulism.

PLoS One 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, COA of Formula: C6H5F4NO3S.

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