Shtamburg V. The aryl- and heterylglyoxals interaction with the substituted ureas, amides and C-nucleophiles

Object - condensation of arylglyoxals and heterylglyoxals interaction with N- and C-nucleophiles. Purpose - investigation of arylglyoxals and heterylglyoxals interaction with N- and C-nucleophiles; research of structure and chemical properties of aryl(heteryl)glyoxals new derivatives. Methods – organic synthesis, NMR 1H and 13C spectroscopy, IR- spectroscopy, mass-spectrometry, X-ray and elementary analysis. Results – тhe scheme of the reaction of arylglyoxals with N-hydroxyurea have been proposed. The overall method of 3-hydroxy-5-arylhydantoines synthesis have been created. In N-alkoxy-N-(1-pyridinium)ureas the high degree of nitrogen atom pyramidality and difference on N-C amide bond have been established. It was found the some elongation of N-N+ bond and some shortening of N-OAlk bond which indicated on the nO-6*N-N+.orbital interaction domination. For the products of the reaction of 4-X-phenylglyoxals (X = F, Cl, Br) with N,N-dimethylhydrazone of 2-furanaldehyde the possibility of the spontaneous а-в-acyloine izomerization was found. It was found that at the chlorination of 3-alkoxy-5-arylimidazolidin-2,4-diones, N-[hydroxy-(2-thenoyl)]methylamides and N-[hydroxy-(2-thenoyl)-methyl]arenesulphonylamides by tert-butylhypochlorite the N-chloro derivatives selectively formed. Area of application – organic chemistry.