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Cu-catalyzed three-component couplings of vinylazaarenes, B2(pin)2, and N-Boc imines are described. Oxidation of the initially formed boronate gives azaarene-containing, Boc-protected amino alcohols with reasonable to good diastereoselectivities.

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The present invention relates to isothiazoles of general formula (I) which inhibit the mitotic checkpoint : in which A, R1 and R2 are as defined in the claims, to methods of preparing said compounds, to intermediate compounds useful for preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of neoplasms, as a sole agent or in combination with other active ingredients.

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The rates of reaction of 2-chloroquinoxaline with aniline, piperidine and triethylamine in methanol, ethanol, n-propanol, i-propanol and n-butanol have been measured at 40 deg C.The results are analysed to correlate the rates with bulk medium properties and also by means of the Brownstein relation.For selected reaction systems the rates have also been measured at two other temperatures to estimate the activation parameters.

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Potassium trifluoroboratoketohomoenolates were prepared in good yields from either the corresponding alpha,beta-unsaturated compounds or methyl ketones. These organoboron reagents were effectively cross-coupled with various aryl and heteroaryl chlorides.

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A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base-free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.

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(Chemical Equation Presented) This paper describes the preparation of twenty-eight derivatives of 1-(2-pyrimidinyl)piperazine as potential antianxiety, antidepressant, and antipsychotic agents. In twenty-six of the preparations a chloro nitrogen heterocycle was caused to react with an excess of 1-(2-pyrimidinyl)piperazine in the absence of solvent. A specific example is given above.

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The kinetics of alkaline hydrolysis of 2-chloroquinoxaline (QCl) with hydroxide ion was investigated spectrophotometrically at different percentages of aqueous-organic solvent mixtures with acetonitrile (10-60% v/v) and with dimethylesulphoxide (10-80%) over the temperature range from 25 to 45 C. The reaction was performed under pseudo first order conditions with respect to 2-chloroquinoxaline (QCl). An increase in the percentage of organic solvent (v/v) has different effects on the reaction rate constants, presumably due to hydrogen bond donor and acceptor differences of the media and other solvatochromic parameters. The data were discussed in terms of the Kamelt-Taft parameter and ET(30). A nonlinear relation between the logarithm of the rate constant and reciprocal of the dielectric constant suggests the presence of selective solvation by the polar water molecules. Activation parameters deltaH#, deltaS# and deltaG# were determined and discussed. Springer Science+Business Media, LLC 2011.

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The palladium(0)-catalysed coupling of 2-haloquinoxalines with functionally substituted alkynes, addition of one mol equivalent of bromine to the 2-alkynylquinoxalines thus produced and then reaction of the resulting dibromides with disodium trithiocarbonate produced 2-hydroxymethyl- and 2-(diethoxymethyl)thieno[2,3-b]quinoxalines. Addition of bromine to some 6-substituted-2-(3,3-diethoxypropyn-1-yl)quinoxalines gave pyrrolo[1,2-a]quinoxalines. Treatment of a 3-(1,2-dibromoalkenyl)quinoline, a 3-(1,2-dibromoalkenyl)pyrazine, and a 5-(1,2-dibromoalkenyl)-pyrimidine with disodium trithiocarbonate failed to induce thiophene ring formation.

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Readily available alpha,alpha-dichlorotoluenes enter a vicarious nucleophilic substitution (VNS) reaction with electron-deficient arenes to give alpha-chlorobenzylated nitrobenzenes, as well as six- and five-membered heterocycles. Oxidation of the initially formed alpha-chlorobenzylic carbanions instead of protonation results in formation of diaryl ketones, providing a means for overall nucleophilic C-H benzoylation of electron-deficient aromatic rings. Alternatively, benzoylated nitroarenes can be obtained via the reaction of isolated alpha-chlorodiarylmethanes with sodium azide.

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Reaction of triphenylphosphine with trichloroisocyanuric acid in no solvent or an ionic liquid gave the corresponding phosphonium chloride, which can be used as a cheap and safe chlorinating reagent. Conversion of hydroxyheterocycles to chloroheterocycles, carboxylic acids to carboxylic acid chlorides, and primary amides to nitriles were accomplished by using the phosphonium chloride in excellent to good yields.

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