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

Berney Daniel | Zendy; Schuh Karlheinz | Zendy

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

Author(s) -

Berney Daniel,

Schuh Karlheinz

Publication year - 1980

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19800630705

Subject(s) - chemistry , pyrrolidine , naphthalene , ring (chemistry) , intramolecular force , medicinal chemistry , stereochemistry , organic chemistry

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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