Skalenko Y. Photochemical synthesis of azabicyclo[3.2.0]-heptane and azabicyclo[4.2.0]octane derivatives and study of their properties

The dissertation introduces a pioneering universally applicable method for the synthesis of bicyclic saturated azaheterocycles. This method employs intramolecular and intermolecular [2+2] cycloaddition reactions, utilizing benzophenone as a photosensitizer and irradiation at a wavelength of 365 nm. The validity of this approach is evidenced through the successful synthesis of a series of novel 2- and 3-azabicyclo[3.2.0]heptanes as well as 3-azabicyclo[4.2.0]octanes. Reaction conditions were optimized to enable scalable synthesis, crucial for medical and industrial chemistry needs. The scope of the proposed methods was explored using various alkenes (non-activated, push-pull, electron-rich, and electron-deficient), homologs, and isomers. The alkenes used included mono-substituted, 1,1-disubstituted, 1,2-disubstituted, and 1,1,2-trisubstituted alkenes. Additionally, the possibility of converting cycloadducts into diverse building blocks, such as amines, diamines, and amino acids, was demonstrated for the first time. The amines synthesized in the course of the research were used for the synthesis of sulfonamide derivatives, which demonstrated significant anticancer activity.