Smetanin M. Synthesis and reactions of annulated pyridines

The dissertation is devoted to the synthesis, chemical and pharmacological properties of annelated pyridines, namely hydrogenated quinolines and halogenated hydrogenated acridines. Obtaining such products by the interaction of electrophilic agents and heterocyclic compounds with the heminal arrangement of nitrogen and oxygen atoms is a promising area of modern research and is becoming an important area of fundamental organic chemistry. The study of the rearrangement of six-membered and five-membered heterocyclic systems under the action of electrophilic reagents is an important and urgent problem, because it is a way to obtain not only compounds with wide potential pharmacological properties, but also new building blocks to expand the search for new substances for pharmacology and science in general. The synthesis of 1,4-diazaspiro[4.5]decan-2-one derivatives as new model heterocyclic five-membered compounds with the hemispherical arrangement of nitrogen atoms was carried out by boiling glycine amide with the corresponding ketones for 18 hours with the addition of an equimolar amount of triethylamine. in methanol. Their interaction with Vilsmeier-Haack reagent was studied. It has been found that the use of a threefold excess of formylating agent rearranges the starting compounds by breaking the imidazolidine ring and then adding the equivalent of the formyl group, followed by recycling and the formation of previously unknown annelated 3-aminopyridines.