Synthesis and some reactions of functionalized 11,12-dihydro-5H-dibenzo[b,g]azonines

Dihydro-5H-dibenzo[b,g]azonine-6,13-dione (2) has been used as a precursor in the synthesis of the indolo[2,3-e]dibenzo[b,g]azonine and tribenzo[b,g,j][1,6] diazacyclododecine ring systems 6 and 7 respectively via a Fischer indolization/periodate oxidation sequence. Fischer indolization of the (1,4-phenylenedihydrazono) derivative 8 gave the polycyclic system 9. The Schmidt reaction of 2 led to the formation of the benzimidazo[1,2-b] [2]benzazepine ring system 11. The Mannich reaction of 2 led to the spirocyclic system 15. The reactions of 2 with aldimines and aromatic aldehydes were also investigated.