Category: 13472-84-9

Connon, Stephen J.; Hegarty, Anthony F. published the artcile< Substituted 3,4-pyridynes: clean cycloadditions>, Category: pyridine-derivatives, the main research area is alkoxypyridine regioselective lithiation elimination; pyridyne regioselective preparation Diels Alder furan; epoxydihydroisoquinoline preparation; isoquinoline epoxydihydro preparation.

The stabilization of 3,4-pyridyne by an alkoxy group adjacent to the ring nitrogen is reported. The regioselective lithiation of 2-ethoxy-, 2-methoxy-, 2-isopropoxy- and 6-isopropoxy-, -3-chloropyridines with tert-butyllithium at low temperatures, followed by elimination of lithium chloride affords 2- and 6-alkoxy-3,4-pyridynes. These species are trapped in situ with furan in a Diels-Alder reaction to give epoxydihydroisoquinolines, e.g. I, in 66-89% yield, and do not give products typical of polymerization or nucleophilic addition to the 3,4-pyridyne intermediates. As a comparison treatment of 3-chloropyridine with furan and LDA gives only 19% of adduct I. The novel use of the isopropoxy group in these systems enhanced regioselectivity by sterically inhibiting α-lithiation by tert-butyllithium.

Perkin 1 published new progress about Diels-Alder reaction. 13472-84-9 belongs to class pyridine-derivatives, and the molecular formula is C6H6ClNO, Category: pyridine-derivatives.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Stavber, Stojan; Zupan, Marko published the artcile< Reactions of cesium fluoroxysulfate with pyridine>, Name: 3-Chloro-2-methoxypyridine, the main research area is pyridine fluorination cesium fluoroxysulfate solvent effect.

Pyridine readily reacts with CsSO4F in various solvents at room temperature producing a mixture of up to three products (2-fluoropyridine, 2-pyridyl fluorosulfonate and 2-chloro or 2-alkoxypyridine), their distribution strongly depending on the solvent used. Reaction of 3-chloropyridine with CsSO4F in methanol leads regioselectively to 2-methoxy-3-chloropyridine, while 3-methylpyridine was converted into 2-methoxy-3-Me and 2-methoxy-5-methylpyridine in a 2:1 relative ratio.

Tetrahedron Letters published new progress about Fluorination. 13472-84-9 belongs to class pyridine-derivatives, and the molecular formula is C6H6ClNO, Name: 3-Chloro-2-methoxypyridine.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Akporji, Nnamdi; Thakore, Ruchita R.; Cortes-Clerget, Margery; Andersen, Joel; Landstrom, Evan; Aue, Donald H.; Gallou, Fabrice; Lipshutz, Bruce H. published the artcile< N2Phos - an easily made, highly effective ligand designed for ppm level Pd-catalyzed Suzuki-Miyaura cross couplings in water>, Electric Literature of 13472-84-9, the main research area is phosphine biaryl ligand preparation crystal structure mol; biaryl preparation; aryl halide arylboronic acid Suzuki Miyaura palladium catalyst.

A new biaryl phosphine-containing ligand from an active palladium catalyst for ppm level Suzuki-Miyaura couplings to afford biaryls, was enabled by an aqueous micellar reaction medium. A wide array of functionalized substrates including aryl/heteroaryl bromides were amenable, as were, notably, chlorides. The catalytic system was both general and highly effective at low palladium loadings (1000-2500 ppm or 0.10-0.25 mol%). D. functional theory calculations suggested that greater steric congestion in N2Phos induced increased steric crowding around the Pd center, helping to destabilize the 2 : 1 ligand-Pd(0) complex more for N2Phos than for EvanPhos (and less bulky ligands), and thereby favoring formation of the 1 : 1 ligand-Pdo complex that is more reactive in oxidative addition to aryl chlorides.

Chemical Science published new progress about Aryl halides Role: RCT (Reactant), RACT (Reactant or Reagent). 13472-84-9 belongs to class pyridine-derivatives, and the molecular formula is C6H6ClNO, Electric Literature of 13472-84-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Beller, Matthias; Magerlein, Wolfgang; Indolese, Adriano F.; Fischer, Christine published the artcile< Efficient palladium-catalyzed alkoxycarbonylation of N-heteroaryl chlorides - A practical synthesis of building blocks for pharmaceuticals and herbicides>, Formula: C6H6ClNO, the main research area is butyl pyridinecarboxylate preparation; heteroaryl chloride alkoxycarbonylation palladium phosphine ligand catalyst; alkoxycarbonylation chloropyridine palladium catalyst.

The alkoxycarbonylation of various N-heteroaryl chlorides was examined in detail. Studies of the butoxycarbonylation of 2- and 3-chloropyridine revealed the importance of selecting both the right phosphine ligand and ligand concentration in order to obtain efficient conversion and selectivity. Amongst the different ligands tested, 1,4-bis(diphenylphosphino)butane (dppb) and 1,1′-bis(diphenylphosphino)ferrocene (dppf) led to the most efficient palladium catalyst systems for the conversion of 2- and 4-chloropyridines and similar heteroaryl chlorides. For e.g., Bu pyridine-2-carboxylate was prepared in 95% yield in the presence of dppf ligand. The best catalytic systems for the alkoxycarbonylation of less activated substrates, such as 3-chloropyridines, were found to be those containing 1,4-bis(dicyclohexylphosphino)butane. Good to excellent yields of a number of N-heterocyclic carboxylic acid esters were realized by applying the appropriate ligand in the right concentration at low catalyst loadings (0.005-0.5 mol% Pd). For the first time catalyst turnover numbers (TON) of up to 13,000 were obtained for the carbonylation of a (hetero)aryl chloride.

Synthesis published new progress about Alkoxycarbonylation. 13472-84-9 belongs to class pyridine-derivatives, and the molecular formula is C6H6ClNO, Formula: C6H6ClNO.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Beller, Matthias; Magerlein, Wolfgang; Indolese, Adriano F.; Fischer, Christine published the artcile< Efficient palladium-catalyzed alkoxycarbonylation of N-heteroaryl chlorides - A practical synthesis of building blocks for pharmaceuticals and herbicides>, Formula: C6H6ClNO, the main research area is butyl pyridinecarboxylate preparation; heteroaryl chloride alkoxycarbonylation palladium phosphine ligand catalyst; alkoxycarbonylation chloropyridine palladium catalyst.

The alkoxycarbonylation of various N-heteroaryl chlorides was examined in detail. Studies of the butoxycarbonylation of 2- and 3-chloropyridine revealed the importance of selecting both the right phosphine ligand and ligand concentration in order to obtain efficient conversion and selectivity. Amongst the different ligands tested, 1,4-bis(diphenylphosphino)butane (dppb) and 1,1′-bis(diphenylphosphino)ferrocene (dppf) led to the most efficient palladium catalyst systems for the conversion of 2- and 4-chloropyridines and similar heteroaryl chlorides. For e.g., Bu pyridine-2-carboxylate was prepared in 95% yield in the presence of dppf ligand. The best catalytic systems for the alkoxycarbonylation of less activated substrates, such as 3-chloropyridines, were found to be those containing 1,4-bis(dicyclohexylphosphino)butane. Good to excellent yields of a number of N-heterocyclic carboxylic acid esters were realized by applying the appropriate ligand in the right concentration at low catalyst loadings (0.005-0.5 mol% Pd). For the first time catalyst turnover numbers (TON) of up to 13,000 were obtained for the carbonylation of a (hetero)aryl chloride.

Synthesis published new progress about Alkoxycarbonylation. 13472-84-9 belongs to class pyridine-derivatives, and the molecular formula is C6H6ClNO, Formula: C6H6ClNO.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Lai, Long-Li; Lin, Pen-Yuan; Wang, Jy-Shih; Hwu, Jih Ru; Shiao, Min-Jen; Tsay, Shwu-Chen published the artcile< Substituent effect on the chlorination of 2-alkoxypyridines to give 2-chloropyridines under Vilsmeier-Haack conditions>, Synthetic Route of 13472-84-9, the main research area is substituent effect chlorination alkoxypyridine.

Various substituted 2-alkoxypyridines were converted into the corresponding 2-chloropyridines in 28-91% yield by use of POCl3 and DMF. Me, halogen, ester and nitro groups displayed an activating effect and an amino group exhibited a deactivating effect.

Journal of Chemical Research, Synopses published new progress about Chlorination. 13472-84-9 belongs to class pyridine-derivatives, and the molecular formula is C6H6ClNO, Synthetic Route of 13472-84-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Nelson, Todd D.; Crouch, R. David published the artcile< Cu, Ni, and Pd mediated homocoupling reactions in biaryl syntheses: The Ullmann reaction>, Reference of 13472-84-9, the main research area is review Biaryl; review Homocoupling; review Pd; review Reaction; review Syntheses; review Ullmann; review Ni; review Cu; review Reactions; review Mediated.

A review of the article Cu, Ni, and Pd mediated homocoupling reactions in biaryl syntheses: The Ullmann reaction.

Organic Reactions (Hoboken, NJ, United States) published new progress about Organic synthesis. 13472-84-9 belongs to class pyridine-derivatives, and the molecular formula is C6H6ClNO, Reference of 13472-84-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Abramovitch, Rudolph A.; Helmer, Friederike; Liveris, M. published the artcile< Aromatic substitution. XVIII. Kinetics of reactions between some halopyridines and -picolines and their N-oxides with methoxide ion in methanol and in dimethyl sulfoxide. Effect of alkyl groups on rates and orientation in nucleophilic aromatic substitution>, Safety of 3-Chloro-2-methoxypyridine, the main research area is SUBSTITUTION AROM KINETICS; PIRIDINES SUBSTITUTION; KINETICS SUBSTITUTION AROM; AROM SUBSTITUTION KINETICS.

The rates and activation parameters for the reactions of 2-fluoro-, 2-chloro-, 2-bromo-, 2-chloro-3-methyl-, 2-chloro-5-methyl-, 2-bromo-3-methyl-, 2-bromo-5-methyl-, 2,3-dichloro-, 2,5-dichloro-, 2-chloro-3-nitro-, and 2-chloro-5-nitropyridines, and of 2-bromo-, 2-bromo-3-methyl-, and 2-bromo-5-methylpyridine N-oxides with MeOK in methanol were determined and compared. The kinetics of the reaction of 2-bromo-, 2-bromo-3-methyl-, and 2-bromo-5-methyl-pyridine and methoxide ion in Me2SO containing small amounts of methanol were also determined; the rates were very sensitive to the methanol concentration The rates were in the order 2-halo- > 2-halo-3-methyl- > 2-halo-5-methyl-, and were dependent upon Eact when the halogen was Br but upon ΔS when it was Cl. The effects of the β-substituent in the pyridine nucleus upon the orthopara ratios are discussed in terms of their effects upon the energies and entropies of activation. 29 references.

Journal of the Chemical Society [Section] B: Physical Organic published new progress about Activation energy. 13472-84-9 belongs to class pyridine-derivatives, and the molecular formula is C6H6ClNO, Safety of 3-Chloro-2-methoxypyridine.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Montanucci, M. published the artcile< A convenient synthesis of bipyridines by nickel-phosphine complex-mediated homo coupling of halopyridines>, Category: pyridine-derivatives, the main research area is coupling halopyridine; bipyridine methoxy; pyridine halo coupling; nickel phosphine complex coupling catalyst.

Coupling of 2-bromopyridine in DMF in the presence of Ni(PPh3)4, prepared in situ from NiCl2, PPh3, and Zn, gave 68% 2,2′-bipyridine. Among the 10 other compounds similarly prepared were: 4,4′-biquinoline and 2,2′-dimethoxy-3,3′-bipyridine.

Synthesis published new progress about Coupling reaction. 13472-84-9 belongs to class pyridine-derivatives, and the molecular formula is C6H6ClNO, Category: pyridine-derivatives.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Testaferri, Lorenzo; Tiecco, Marcello; Tingoli, Marco; Bartoli, Donatella; Massoli, Alberto published the artcile< The reactions of some halogenated pyridines with methoxide and methanethiolate ions in dimethylformamide>, Application of C6H6ClNO, the main research area is pyridine dihalo substitution methoxide alkanethiolate; halopyridine substitution methoxide alkanethiolate; substitution dihalopyridine methoxide alkanethiolate; mercaptopyridine; alkylthiopyridine.

Dihalopyridines I (R = 2-Br, R1 = 5-, 6-Br; R = 2-, 5-Cl, R1 = 3-Cl) reacted with NaSR2 (R2 = Me, CHMe2) in DMF to give 73-96% mono- or bis-substitution products I (R = SR2) or I (R = R1 = SR2), depending upon reaction conditions. The dihalo compounds reacted with NaOMe to give 72-93% I (R = OMe), but bis-substitution occurred easily only for I (R = 2-Br, R1 = 6-Br; R = 5-Cl, R1 = 3-Cl). Some I [R(R1) = OMe, R1(R) = SMe] were prepared by further reaction of monosubstitution products. I (R = R1 = SCHMe2 were fragmented by Na-HMPA to give I (R = R1 = SH), which were isolated as I (R = R1 = SMe) in 63-80% yield.

Tetrahedron published new progress about Nucleophilic aromatic substitution reaction. 13472-84-9 belongs to class pyridine-derivatives, and the molecular formula is C6H6ClNO, Application of C6H6ClNO.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem