The important role of 2-Chloroquinoxaline

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Synthesis of a cobalt complex of a pyrano[2,3-b]quinoxaline-3,4-dithiolate related to molybdopterin

Cobalt complex 2 has been synthesised in which the key features of molybdopterin – a dithiolene ligand on a tetrahydropyrano[2,3-b]pyrazine – are modelled.

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Pd/PTABS: Catalyst for Room Temperature Amination of Heteroarenes

A mild and highly efficient catalytic amination procedure for chloroheteroarenes at ambient temperature using the Pd/PTABS catalytic system is reported. The protocol is selective for the amination of chloroheteroarenes using secondary amines such as piperidine, pyrrolidine, and several others. The exceptional mildness of the developed protocol is beneficial for the synthesis of a crucial Buparlisib intermediate as well as the formal synthesis of Alogliptin in competitive yields.

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Green chemical synthesis of 2-benzenesulfonyl-pyridine and related derivatives

A practical synthesis of 2-benzenesulfonylpyridine, 1, is described which is a key starting material for the manufacture of an investigational new drug candidate at Eli Lilly and Company. An optimized green chemical process was developed which features a novel tandem SNAr/oxidation under mild conditions to produce the target sulfone, 1, in 86% yield and>99% purity. In addition, this novel, environmentally friendly methodology was found to be general for the synthesis of substituted aromatic pyridyl sulfides and sulfones.

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Discovery of 2-Chloroquinoxaline

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Photoreactions in Crystals with Ethenes: Selectivities and Crystal Engineering

Photoreactions in crystals of sterically hindered dimethylenecyclopentanones 1 and trimethylenecyclopentanes 4 lead to E/Z isomerizations and 1,5-H shifts.The stereochemical result of the photodimerization in the crystalline state of the heterostilbenes 6 is apparently determined by the polarity (dipole moment), which governs the crystal packing as well.A strong dissymmetry of charge (as in 6a-g) gives rise to H(ead)/T(ail)-syn dimers 7.This correlates well with the molecular stacking in the crystals of 6c, as determined by X-ray analysis.A low dissymmetry of charge (as in 6h) leaves the crystals photostable.At medium polarity two products with H/T-syn and H/H-syn stereochemistry (7 and 8) or, in particular cases, only dimers of type 8 are formed.The precise stereochemistry is proved by comparison with the analyzed 1H-NMR parameters of esters of truxillic and truxinic acids.Bifunctional heterostilbenes like 12c are photostable in the crystalline state.However, strongly polar methoxycarbonyl (13) and acetyl groups (17, 21) lead to photoreactive crystals again.In the case of 17 this is also shown by X-ray analysis.Due to well-defined possibilities of movement, there are three products formed in terms of multiproduct topochemistry. 13 and 21 also form several products upon photoreaction in the crystal.

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Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters

A highly active and efficient catalyst system derived from a palladium precatalyst and monophosphine ligands 1 or 2 for the Suzuki-Miyaura cross-coupling reaction of heteroaryl boronic acids and esters has been developed. This method allows for the preparation of a wide variety of heterobiaryls in good to excellent yields and displays a high level of activity for the coupling of heteroaryl chlorides as well as hindered aryl and heteroaryl halides. Specific factors that govern the efficacy of the transformation for certain heterocyclic motifs were also investigated.

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Extracurricular laboratory:new discovery of 2-Chloroquinoxaline

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Aryloxyaniline base third ester compound and its use as herbicides (by machine translation)

Aryloxyaniline base third acid ester compound, comprising the following general formula (I) the structure of the said: The heteroaromatic ring wherein Ar or thick heterocyclic; Heteraromatic ring The fused heterocycle R 1, R 2, R 3, R 4 is H, halogen, nitro, methoxy, methyl, carboxylic acid carbonyl, cyano or trihalo methyl in one kind or several kinds of; R 5 to H, C1-C4 of the straight-chain or branched-chain alkyl, alkyl is of hydrogen is hydroxy, carboxyl, mercapto, amino, guanidino, phenyl-substituted; R 6 is methyl, ethyl, butyl, A in; the utility model has the advantages that: the structure of the compound, can keep esters fragrant oxygen benzene oxygen third Weedicide efficient, quick-acting, is not easy to produce the resistance, and the like; at the same time can be designed the amino acid functional group in the molecule as adulterations amino acid, to inhibit the biosynthesis of the protein plant itself, and the role of all weeds. (by machine translation)

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REGIOSELECTIVE SYNTHESIS OF 2,6-DICHLOROQUINOXALINE AND 2-CHLORO-6-IODOQUINOXALINE

Facile regioselective synthesis of 2,6-dichloroquinoxaline and 2-chloro-6-iodoquinoxaline is described.Electrophilic substitution reaction of 2(1H)-quinoxalinone with chloride and iodide ion in 95percent sulfuric acid occurred at 6-position exclusively.

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Preparation of 4-heteroaryl-4-cyanopiperidines via SNAr substitution reactions

The scope and limitations of SNAr substitution reactions of metalated 4-cyanopiperidines with heterocyclic halides were explored. These facile reactions provide rapid access to a wide range of 4-heteroaryl-4-cyanopiperidines and have resulted in improved yields, faster reaction times, and lower temperatures than previously published synthetic methods.

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Synthesis of new quinoxaline derivatives

New quinoxaline derivatives were prepared by the reaction of 2-hydroxyquinoxaline 1 and alkyl or alkylaminoalkyl halides in dimethylformamide using potassium carbonate as a base. The hydroxyl group was readily converted into a thiol function by treatment with phosphorus pentasulfide and/or Lawesson’s reagent in pyridine, and the subsequent alkylation of the thiol group was carried out under phase-transfer catalyst conditions. Chlorination of 1 was carried out with phosphorus oxychloride. Branching of alkylamino side chains to the 2-OH, 2-SH, and 2-Cl quinoxalines resulted in the synthesis of several compounds. Synthesis and alkylation of 2-hydroxy 7-nitroquinoxaline are also reported.

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Survey of the electrochemical behavior of chlorinated pyrazines, quinoxalines, and pyridazines at carbon and mercury cathodes

Cyclic voltammetry and controlled-potential electrolysis have been employed to examine the electrochemical behavior of some mono- and dichlorinated pyrazines, quinoxalines, and pyridazines at carbon and mercury cathodes in either acetonitrile or dimethylformamide containing a tetraalkylammonium salt. Unsubstituted pyrazine and pyridazine each exhibit a single reduction wave, whereas unsubstituted quinoxaline shows three cathodic waves. For the chlorinated compounds, an additional wave is seen for the reduction of each carbon-chlorine bond. Depending on the potential of the cathode, bulk electrolyses of dichlorinated pyrazines or quinoxalines afford either the monochlorinated or fully dechlorinated product, whereas the monochlorinated analogues undergo reduction to the dechlorinated species. Electrolyses of chlorinated pyridazines give dark colored solutions, but the products (apparently polymeric) cannot be detected or identified by means of conventional GC, GC-MS, and HPLC techniques.

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