Heterocyclic Spiro-naphthalenones. Part VI. Some reactions with spiro [naphthalene-2 (1H), 2′-pyrrolidine]-1,5′-dione leading to various 6-, 7-, 8-, 9-, 10- and 11-membered azacycloalkanes

The spirolactam 5 was reduced to the spiro[naphthalene, pyrrolidine] 7 which was N-aralkylated to give 9 and 17 . Cyclization of 9 gave the phenanthridines 10 and 11 ; similarly, 17 afforded the 7- and 8-membered heterocycles 18 and 19 . Compounds 10, 18 and 19 when subjected to an intramolecular Hofmann elimination yielded the 9-, 10- and 11-membered ring systems, respectively 16, 22 and 23 .