Synthesis of 1-azabicyclo[3.3.1]nonadienes by intramolecular cyclization of 1-(3-oxo-2-phenylbutyl)tetrahydropyridines

✍ Scribed by Sólyom, Sándor ;Pallagi, István ;Ábrahám, Gizella ;Ling, István ;Szöllõsy, Márta ;Sziráki, István ;Jerkovich, Gyula

• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 507 KB
• Volume: 1995
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.1995199511287

✦ Synopsis

Abstract

Intramolecular cyclization reactions were performed with 1‐(3‐oxo‐2‐phenylbutyl)‐1,2,5,6‐tetrahydropyridine derivatives 6a‐h in sulfuric acid to give 3,6‐diphenyl‐substituted 1‐aza‐bicyclo[3.3.1]nonadienes 9. The intermediate carbinols 7a‐f and 8b, c could be isolated. Carrying out the reaction in methanesulfonic acid stereoselectivity was found in the formation of carbinols with preferential production of derivatives 7. Some of the compounds 9 show remarkable dopamine uptake inhibition.