Konzeptionelle Synthesestrategien zur diversitätsorientierten Darstellung anellierter N-heterocyclischer Scaffolds via Multikomponenten-Reaktionen

The doctoral thesis is focused on the synthesis of potentially pharmacologically interesting five-, six-, and seven-membered N-heterocycles. An important role for the construction of these heterocycles is given to multicomponent reactions. These reactions enable the direct formation of both the targeted heterocyclic systems and the precursors for subsequent cyclizations. The sequential use of the ASINGER- and UGI-multicomponent reaction followed by a cyclization represents an innovative synthetic route to 1,4-benzodiazepine-2,5-diones. Following the same strategy, bisamides that contain the substructure of thiazolidines are synthesized and then transformed via an unexpected Cu-mediated rearrangement to tricyclic thiomorpholine structures. Another project deals with the development of a new multicomponent reaction towards benzannulated six-membered lactams. The potential of feasible derivatizations is exemplified by subsequent Pd-catalyzed and Cu-catalyzed conversions. Furthermore, a diversity-oriented multicomponent reaction to 4-hydroxy-3,4-dihydro-2H-1,3-thiazine-2-thiones is presented. Based on these heterocycles, various derivatisations are investigated. Finally, a ligand-directed Cu-mediated reaction to pyrrolo or indolo annulated dihydroquinoxalines and quinoxalines is described.