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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

✍ Scribed by Daniel Berney; Karlheinz Schuh

Publisher
John Wiley and Sons
Year
1980
Tongue
German
Weight
379 KB
Volume
63
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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.

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