Pyridine-derivatives

Sankar, Velayudham published the artcileZinc-Catalyzed N-Alkylation of Aromatic Amines with Alcohols: A Ligand-Free Approach, Category: pyridine-derivatives, the publication is Advanced Synthesis & Catalysis (2020), 362(20), 4409-4414, database is CAplus.

An efficient zinc-catalyzed N-alkylation reaction of aromatic amines was achieved using aliphatic, aromatic and heteroaromatic alcs. as the alkylating reagent. A variety of aniline derivatives, including heteroaromatic amines, underwent the N-alkylation reaction and furnished N-alkyl amines in good to excellent yields. The application of reaction was also further demonstrated by the synthesis of 2-phenylquinoline from acetophenone and 2-aminobenzyl alc. Deuterium labeling experiments showed that the reaction proceeded via a borrowing hydrogen process.

Advanced Synthesis & Catalysis 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, Category: pyridine-derivatives.

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

Rabasco, John J. published the artcileReactions of strong bases with vinyl fluoride. Formation and characterization of 1-fluorovinyl anion and the fluoride-acetylene hydrogen-bonded complex, Recommanded Product: 1-Fluoropyridiniumtriflate, the publication is Journal of the American Society for Mass Spectrometry (1992), 3(2), 91-8, database is CAplus and MEDLINE.

Vinyl fluoride reacts with strong bases to afford 1-fluorovinyl anion (1a) and a fluoride-acetylene cluster. The former ion can be prepared independently, and cleanly, by the fluorodesilylation of 1-(trimethylsilyl)fluoroethylene. Reactions of 1a are reported, and its proton affinity is assigned (387 ± 3 kcal mol^-1). Vinyl fluoride is 22 kcal mol^-1 more acidic than ethylene. This unusually large substituent effect is reproduced by ab initio calculations and can be accounted for by geometric changes which minimize the electron-electron repulsion in 1a. Computations on 2-fluorovinyl anions have also been carried out, and both ions are only slightly less stable than 1a. The cis-2-fluorovinyl anion has a larger barrier for fluoride elimination and is a reasonable target for preparation

Journal of the American Society for Mass Spectrometry 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

Simler, Thomas published the artcilePotassium and Lithium Complexes with Monodeprotonated, Dearomatized PNP and PNC^NHC Pincer-Type Ligands, Product Details of C23H43NP2, the publication is Organometallics (2016), 35(6), 903-912, database is CAplus.

The reaction of 2,6-bis(di-tert-butylphosphinomethyl)pyridine (^tBuPN^tBuP) with 1 molar equiv of KCH₂C₆H₅ or LiCH₂SiMe₃ gave M(^tBuP^*N_a^tBuP) (M = K, Li; P^* = vinylic P donor, ^tBuP = P^tBu₂, N_a = anionic amido N donor) after monodeprotonation of the α-lutidinyl-CH₂ and concomitant dearomatization of the heterocycle. Evidence is provided that the anion ^tBuP^*N_a^tBuP may exist as Z- and E-isomers, interconvertible by rotation about the C_α-N-C_α-P exocyclic formal double bond. Thus, the two isomers of K(^tBuP^*N_a^tBuP), i.e., [K{(Z)-(^tBuP^*N_a^tBuP-κP^*,κN_a,κP)}(THF)], 1-Z·(THF), and [K{(E)-(^tBuP^*N_a^tBuP-κN_a,κP)}(THF)], 1-E·(THF), cocrystd. from THF in a 4:1 ratio. However, in the presence of DME, the isomerically pure [K{(E)-(^tBuP^*N_a^tBuP-κN_a,κP)}(DME)₂], 1-E·2(DME), was crystallized The α-picolinyl-CH₂ moiety in ^RPNC^NHC (N = substituted 2-picoline, ^RP = PCy₂, R = Cy; ^RP = P^tBu₂, R = ^tBu; C^NHC = N-heterocyclic carbene) was similarly deprotonated with concomitant dearomatization using LiN(SiMe₃)₂. This afforded the complexes Li(^RP^*N_aC^NHC), which were crystallized as the Z- or E-isomers, [Li{(E)-(^tBuP^*N_aC^NHC-κN_a,κC^NHC)}(Et₂O)₂], 3^tBu-E·2(Et₂O), [Li{(Z)-(^CyP^*N_aC^NHC-κP^*,κN_a,κC^NHC)}(Et₂O)], 3^Cy-Z·(Et₂O), and [Li{(Z)-(^tBuP^*N_aC^NHC-κP^*,κN_a,κC^NHC)}(Et₂O)], 3^tBu-Z·(Et₂O). The Z- and E-isomers reversibly interconvert in solution as shown by ³¹P{¹H} and ⁷Li NMR spectroscopy. The acidity of the α-picolinyl-CH₂ in ^RPNC^NHC is higher than in the known ^tBuPN^tBuP (ca. by 6 pK_a units).

Organometallics published new progress about 338800-13-8. 338800-13-8 belongs to pyridine-derivatives, auxiliary class Bis-phosphine Ligands, name is 2,6-Bis((di-tert-butylphosphino)methyl)pyridine, and the molecular formula is C3H9ClOS, Product Details of C23H43NP2.

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

Rauch, Michael published the artcileMetal-Ligand Cooperation Facilitates Bond Activation and Catalytic Hydrogenation with Zinc Pincer Complexes, COA of Formula: C23H43NP2, the publication is Journal of the American Chemical Society (2020), 142(34), 14513-14521, database is CAplus and MEDLINE.

A series of PNP zinc pincer complexes capable of bond activation via aromatization/dearomatization metal-ligand cooperation (MLC) were prepared and characterized. Reversible heterolytic N-H and H-H bond activation by MLC is shown, in which hemilability of the phosphorus linkers plays a key role. Utilizing this zinc pincer system, base-free catalytic hydrogenation of imines and ketones is demonstrated. A detailed mechanistic study supported by computation implicates the key role of MLC in facilitating effective catalysis. This approach offers a new strategy for (de)hydrogenation and other catalytic transformations mediated by zinc and other main group metals. Safety: caution advised with pyrophoric organozinc compounds, gas evolution at high temperature and reactions involving H₂.

Journal of the American Chemical Society published new progress about 338800-13-8. 338800-13-8 belongs to pyridine-derivatives, auxiliary class Bis-phosphine Ligands, name is 2,6-Bis((di-tert-butylphosphino)methyl)pyridine, and the molecular formula is C23H43NP2, COA of Formula: C23H43NP2.

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

Sato, Masayuki published the artcileReaction of 2,2,6-trimethyl-1,3-dioxin-4-one with isoquinolinium and pyridinium ylides, Name: 1-(Cyanomethyl)pyridin-1-ium chloride, the publication is Chemical & Pharmaceutical Bulletin (1982), 30(12), 4359-64, database is CAplus.

The reactions of diketene-acetone adduct [2,2,6-trimethyl-1,3-dioxin-4-one (I)] with heterocyclic ylides were studied. Heating I with isoquinolinium bis(ethoxycarbonyl)methylide gave pyrroloisoquinoline II (R = CO₂Et). Similarly, isoquinolinium cyano(ethoxycarbonyl)methylide and phenacylide gave pyrroloisoquinolinecarbonitrile III and II (R = Bz), resp. Isoquinolinium dicyanomethylide reacted with I to give bis(methyloxooxazinyl)methylide IV. Pyridinium ylides similarly reacted with I to give indolizines and oxazinylmethylides.

Chemical & Pharmaceutical Bulletin published new progress about 17281-59-3. 17281-59-3 belongs to pyridine-derivatives, auxiliary class Pyridine,Nitrile,Salt, name is 1-(Cyanomethyl)pyridin-1-ium chloride, and the molecular formula is C7H7ClN2, Name: 1-(Cyanomethyl)pyridin-1-ium chloride.

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

Jung, Sungouk published the artcileEffect of substitution of methyl groups on the luminescence performance of Ir^III complexes: Preparation, structures, electrochemistry, photophysical properties and their applications in organic light-emitting diodes (OLEDs), Application of 5-Methyl-2-(p-tolyl)pyridine, the publication is European Journal of Inorganic Chemistry (2004), 3415-3423, database is CAplus.

A series of dimethyl-substituted tris(pyridylphenyl)iridium(III) derivatives [(n-MePy-n’-MePh)₃Ir] [n = 3, n’ = 4 (1); n = 4, n’ = 4 (2); n = 4, n’ = 5 (3); n = 5, n’ = 4 (4); n = 5, n’ = 5 (5)] have been synthesized and characterized to investigate the effect of the substitution of Me groups on the solid-state structure and photo- and electroluminescence. The absorption, emission, cyclic voltammetry and electroluminescent performance of 1–5 have also been systematically evaluated. The structures of 2 and 4 have been determined by a single-crystal x-ray diffraction anal. Under reflux (> 200°) in glycerol solution, fac-type complexes with a distorted octahedral geometry are predominantly formed as the major components in all cases. Electrochem. studies showed much smaller oxidation potentials relative to Ir(ppy)₃ (Hppy = 2-phenylpyridine). All complexes exhibit intense green photoluminescence (PL), which has been attributed to metal-to-ligand charge transfer (MLCT) triplet emission. The maximum emission wavelengths of thin films of 1, 3, 4 and 5 at room temperature are in the range 529-536 nm, while 2 displays a blue-shifted emission band (λ_max = 512 nm) with a higher PL quantum efficiency (Φ_PL = 0.52) than those of complexes 1 and 3–5; this is attributed to a decrease of the intermol. interactions. Multilayered organic light-emitting diodes (OLEDs) were fabricated by using three (2, 3 and 4) of these Ir^III derivatives as dopant materials. The electroluminescence (EL) spectra of the devices, which have the maximum peaks at 509-522 nm, with shoulder peaks near 552 nm, are consistent with the PL spectra in solution at 298 K. The devices show operating voltages at 1 mA/cm² of 4.9, 5.6, 5.1, and 4.6 V for Ir(ppy)₃, 2, 3, and 4, resp. In particular, the device with 2 shows a higher external quantum efficiency (η_ext = 11% at 1 mA/cm²) and brightness (4543 cd/m² at 20 mA/cm²) than Ir(ppy)₃ (η_ext = 6.0% at 1 mA/cm²; 3156 cd/m² at 20 mA/cm²) and other Ir(dmppy)₃ derivatives, (dmppy = dimethyl-substituted ppy), under the same conditions. The Me groups at the meta (Ph) and para (Py) positions to the Ir metal atom have a great influence on absorption, emission, redox potentials and electroluminescence.

European Journal of Inorganic Chemistry published new progress about 85237-71-4. 85237-71-4 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene, name is 5-Methyl-2-(p-tolyl)pyridine, and the molecular formula is C13H13N, Application of 5-Methyl-2-(p-tolyl)pyridine.

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

Takeda, Sunao published the artcileα,α-Gem-difluorination of α-(alkylthio)acetophenone derivatives with N-fluoropyridinium salts, HPLC of Formula: 107263-95-6, the publication is Chemical & Pharmaceutical Bulletin (2000), 48(7), 1097-1100, database is CAplus and MEDLINE.

The α,α-gem-difluorination of 2′,4′-difluoro-α-(methylthio)acetophenone with N-fluoropyridinium salts gave 2′,4′,α,α-tetrafluoro-α-(methylthio)acetophenone. This reaction was accelerated by the addition of zinc chloride, zinc bromide or anhydrous iron(III) chloride, and higher yields than the reaction without additives were obtained. The gem-difluorination reaction using FP-T300 in the presence of zinc bromide was applicable to other α-(alkylthio)acetophenone derivatives

Chemical & Pharmaceutical Bulletin 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 C6H9N3O2S, HPLC of Formula: 107263-95-6.

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

Sato, Masayuki published the artcileSynthesis of 5-fluoro-1,3-dioxin-4-ones: versatile building blocks of fluorinated compounds, Name: 1-Fluoropyridiniumtriflate, the publication is Journal of the Chemical Society, Chemical Communications (1991), 699-700, database is CAplus.

Fluorination of 5,6-unsubstituted dioxinone I (R = H) with F₂ followed by treatment with Et₃N affords the title compound I (R = F) which can be converted into fluorinated derivatives of formylacetic acid, e.g., (E)-AcOCH:CFCO₂Me or of heterocyclic systems, e.g., II and III.

Journal of the Chemical Society, Chemical Communications 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, Name: 1-Fluoropyridiniumtriflate.

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

Nielsen, Martin published the artcileEfficient Hydrogen Production from Alcohols under Mild Reaction Conditions, Synthetic Route of 338800-13-8, the publication is Angewandte Chemie, International Edition (2011), 50(41), 9593-9597, database is CAplus and MEDLINE.

This effective acceptor-less dehydrogenation of alc. employs mild, neutral reaction conditions. The protocol is extended beyond the typical model substrate, iso-Pr alc., to the bio-relevant ethanol. Unprecedented high turnover frequencies for both iso-Pr alc. and ethanol are observed at low temperatures (< 100〈°C).

Angewandte Chemie, International Edition published new progress about 338800-13-8. 338800-13-8 belongs to pyridine-derivatives, auxiliary class Bis-phosphine Ligands, name is 2,6-Bis((di-tert-butylphosphino)methyl)pyridine, and the molecular formula is C23H43NP2, Synthetic Route of 338800-13-8.

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

Yasui, Kosuke published the artcileThe Effect of the Leaving Group in N-Heterocyclic Carbene-Catalyzed Nucleophilic Aromatic Substitution Reactions, Product Details of C5H5BrN2, the publication is Bulletin of the Chemical Society of Japan (2020), 93(12), 1424-1429, database is CAplus.

The reactivity order of the leaving group was F > Cl â‰?Br > I in N-heterocyclic carbene-catalyzed CS_NAr reactions of aryl halides bearing an α,β-unsaturated amide was discussed. Based on a qual. Marcus anal., the nature of the transition state in this catalytic CS_NAr was primarily determined by the potential energy of the Meisenheimer complex, even though it was not involved as a discrete intermediate in the reaction pathway.

Bulletin of the Chemical Society of Japan 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 C14H26O2, Product Details of C5H5BrN2.

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