Frolov K. Cyanoselenoacetamide and its derivatives in the synthesis of selenium- containing azaheterocycles

The dissertation is devoted to the study of directed synthesis of selenium-containing aza-heterocycles and the elaboration of preparative methods for them, starting from cyanoselenoacetamide and its derivatives. It was shown that cyanoselenoacetamide reacts with 2-anilinomethylidene 1,3-dicarbonyl compounds and diethyl ethoxymethylenemalonate to afford selenium-containing quinolones and pyridines, respectively. Partially saturated 3-cyanopyridine-2-selenones, 3-cyano-1,4,5,6,7,8-hexahydroquinolin-2-selenolates and bispidine derivatives were synthesized by multi- component reactions using cyanoselenoacetamide and 3-aryl-2-cyanoselenoacrylamides. Convenient methods for the synthesis of 6-amino-3,5-dicyano-1,4-dihydropyridine-2-selenolates were developed. It was shown that their aminomethylation occurs with the formation of 1,3,5-triazine and diazabicyclononane ring systems to give 8-selenoxo-3,5,7,11-tetraazatricyclo[7.3.1.02,7]tridec-2-ene derivatives. The results of the oxidation, aminomethylation and Hantzsch reaction with 3-aryl-2-cyanoselenoacrylamides are discussed.