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Suzuki-Miyaura coupling of heteroaryls is an important method for the preparation of compound libraries for medicinal chemistry and materials research. Although many catalysts have been developed, none of them have been generally applicable to the coupling reactions of heteroaryl chlorides and tosylates at room temperature. We discovered that a catalyst combination of Pd(OAc)2 and XPhos (2-dicyclohexylphosphanyl-2′,4′,6′- triisopropylbiphenyl) could efficiently catalyze these couplings. Besides the choice of catalyst, the use of hydroxide bases in an aqueous alcoholic solvent was essential for fast couplings. These conditions promoted fast release of active catalyst (XPhos)Pd0, and accelerated the transmetalation in the catalytic cycle. Most of the major families of heteroaryl chlorides (31 examples) and tosylates (17 examples) reached full conversion within minutes to hours at room temperature. The method could be easily scaled up for gram-scale synthesis. Furthermore, we examined the relative reactivity of coupling partners in whole reactions. Electron-rich heteroaryl chlorides and tosylates reacted more slowly than electron-deficient ones, in the order of indole, pyrrole < furan, thiophene < pyridine and other six-membered-ring azines. For heteroarylboronic acids, the reactivity ranking was reversed: indole, pyrrole > furan, thiophene > pyridine. Similarly, electron-deficient arylboronic acids were less reactive than electron-neutral and electron-rich ones. The reactivity trends from this study can help to choose appropriate coupling partners for Suzuki reactions.

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Reference:
Quinoxaline – Wikipedia,
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In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 1448-87-9, name is 2-Chloroquinoxaline, introducing its new discovery. category: quinoxaline

Imaging agents of formula (I) and methods for detecting neurological disorders comprising administering to a patient in need compounds of formula (I) capable of binding to tau proteins and beta-amyloid peptides are presented herein. The invention also relates to methods of imaging Abeta and tau aggregates comprising introducing a detectable quantity of pharmaceutical formulation comprising a radiolabeled compound of formula (I) and detecting the labeled compound associated with amyloid deposits and/or tau proteins in a patient. These methods and compositions enable preclinical diagnosis and monitoring progression of AD and other neurological disorders.

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Suzuki-Miyaura cross-coupling reaction with 2-heteroarylboronic acids is generally challenging due to these acids easy decomposition. To overcome this problem, we developed a coupling method that uses 2-heteroaryl pinacol boronates in the presence of 1.0 mol % Pd(OAc)2 and 2.0 mol % S-Phos with 4 equiv amount of LiOH in dioxane and H2O at 80 C for 30 min. This developed method allowed for the synthesis of a wide variety of 2-heteroaryl pyrimidines from 2-chloropyrimidyl derivatives in high yields, and is also useful in the preparation of various biaryl derivatives from heteroaryl chlorides.

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Aryl aminoacetonitriles are oxidized by NiO2-H2O or MnO2 in the presence of a wide range of NH2-containing compounds to afford aryl amidines, presumably via iminium intermediates. A ‘one-pot’ procedure for the preparation of heteroaryl amidines from N-containing heteroaryl halides through a process comprising sequential SNAr substitution and oxidation has also been developed.

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The compounds of this invention are designated as quinoxalinyl esters of carbamimidothioic acids and exhibit the pharmacological properties of preventing gastric ulcers, reducing gastric secretions and lowering blood pressure. The compounds have the following structural formula: STR1 in which Q is hydrogen or nitro;

A is hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, carbomethoxy, carbethoxy, carbopropoxy, carbisopropoxy, carbobutoxy, carbisobutoxy, or carbo-t-butoxy; and< P>

R 1, R 2, and R 3 are, independently, hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, allyl, or R. sup.1 and R 3 may be concatenated with a carbon chain having 4 carbon atoms with R 2 then being hydrogen; except that, when A and Q are hydrogen, R 1, R 2, and R. sup.3 may not all be hydrogen; and with the further exception that, where A is methyl and R 1, R 2, and Q are all hydrogen, R 3 may not be ethyl;

or a pharmaceutically acceptable salt thereof.

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1448-87-9, Name is 2-Chloroquinoxaline, belongs to quinoxaline compound, is a common compound. Quality Control of 2-ChloroquinoxalineIn an article, once mentioned the new application about 1448-87-9.

Simple iron salts such as FeCln, Fe(acac)n (n = 2,3) or the salen complex 4 turned out to be highly efficient, cheap, toxicologically benign, and environmentally friendly precatalysts for a host of cross-coupling reactions of alkyl or aryl Grignard reagents, zincates, or organomanganese species with aryl and heteroaryl chlorides, triflates, and even tosylates. An “inorganic Grignard reagent” of the formal composition [Fe(MgX)2] prepared in situ likely constitutes the propagating species responsible for the catalytic turnover, which occurs in many cases at an unprecedented rate even at or below room temperature. Because of the exceptionally mild reaction conditions, a series of functional groups such as esters, ethers, nitriles, sulfonates, sulfonamides, thioethers, acetals, alkynes, and -CF3 groups are compatible. The method also allows for consecutive cross-coupling processes in one pot, as exemplified by the efficient preparation of compound 12, and has been applied to the first synthesis of the cytotoxic marine natural product montipyridine 8. In contrast to the clean reaction of (hetero)aryl chlorides, the corresponding bromides and iodides are prone to a reduction of their C-X bonds in the presence of the iron catalyst.

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A bis(eta5-cyclopentadienyl)cobalt complex of a bis-dithiolene: A chemical analogue of the metal centres of the DMSO reductase family of molybdenum and tungsten enzymes, in particular ferredoxin aldehyde oxidoreductase

The synthesis is described of a bis-ene-1,2-dithiolate pro-ligand, designed to model the stereochemical situation in the cofactor of the tungsten enzyme ferredoxin aldehyde oxidoreductase from Pyrococcus furiosus. Each masked ene-1,2-dithiolate unit is mounted on a pyrano[2,3-b]tetrahydroquinoxaline tricycle, comparable to the pyrano[2,3-g]tetrahydropteridines found in all molybdoenzymes and tungsten analogues. Hydrolytic release of the bis-ligand was confirmed by its entrapment as a double (eta5-C5H 5)Co complex.

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AN UNEXPECTED RING-OPENING IN THE REISSERT REACTION ON 2,3-DIPHENYLQUINOXALINE-N-OXIDE.

When quinoxaline-N-oxide 1 is reacted with KCN and benzoyl chloride in water (the Reissert reaction) or methanol, the products are 2-, 5- and 6- chloroquinoxaline (the latter being the major product: 42+/-6percent) and small amounts of 2-cyanoquinoxaline.Using three equivalents of trimethylsilyl cyanide instead of KCN, and dichloromethane as the solvent, leads to a 72percent yield of 2-cyanoquinoxaline.The reaction of trimethylsilyl cyanide and benzoyl chloride with 2,3-diphenylquinoxaline-N-oxide 2 leads to an unexpected ring-opening product 13; its structure is based on spectroscopic data and on an X-ray crystallographic analysis.

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Electric Literature of 1448-87-9, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 1448-87-9, molcular formula is C8H5ClN2, introducing its new discovery.

Rapid Construction of Structurally Diverse Quinolizidines, Indolizidines, and Their Analogues via Ruthenium-Catalyzed Asymmetric Cascade Hydrogenation/Reductive Amination

A rapid construction of enantioenriched benzo-fused quinolizidines, indolizidines, and their analogues by ruthenium-catalyzed asymmetric cascade hydrogenation/reductive amination of quinolinyl- and quinoxalinyl-containing ketones has been developed. This reaction proceeds under mild reaction conditions, affording chiral benzo-fused aliphatic N-heterocyclic compounds with structural diversity in good yields (up to 95 %) with excellent diastereoselectivity (up to >20:1 dr) and enantioselectivity (up to >99 % ee). Furthermore, this catalytic protocol is applicable to the formal synthesis of (+)-gephyrotoxin.

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Potent quinoxaline-based inhibitors of PDGF receptor tyrosine kinase activity. Part 1: SAR exploration and effective bioisosteric replacement of a phenyl substituent

Novel substituted 2-anilino- and 2-cycloalkylaminoquinoxalines have been found to be useful and selective inhibitors of PDGF-R autophosphorylation. Replacement of an anilino-substituent with substituted cyclohexylamino- or norbornylamino substituents led to significant improvements in the pharmacokinetic profile of these analogues.

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Reference:
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