Synthesis of chalcogen-containing aminoazines

Unsaturated nitriles with a nucleophobic group in the β position are used in the synthesis of amino heterocyclic compounds. We have studied, for the first time, reactions of these compounds with cyanothioacetamide and with cyanoselenoacetamide. It was found that the reactions of the α,β-unsaturated nitriles with the amides in ethanol in presence of sodium ethoxide at 25-500C go regioselectively with the formation of sodium 2-pyridinethiolate and sodium 2-pyridineselenolate. On the acidification of the salts in water with hydrochloric acid we obtained the 2(1H)-pyridinechalcogenones. This reaction was applied for the synthesis of the pyrimidine, which was prepared analogously from the compounds with the subsequent acidification of the reaction mixture. The IR spectra were determined with a UR-20 spectrometer on samples pelleted with KBr. The PMR spectra were recorded on a Varian FT-80A spectrometer (80 MHz) in DMSO-d6; standard Me4Si