Synthesis of 1-Azabicyclo[3.3.1]nona-3,6-diene Derivatives by a Modified Prins Reaction

✍ Scribed by Csuzdi, Emese ;Ling, István ;Ábrahám, Gizella ;Pallagi, István ;Sólyom, Sándor

• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: English
• Weight: 800 KB
• Volume: 1994
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199419940406

✦ Synopsis

Abstract

Intramolecular electrophilic cyclization reactions were performed with 1‐(3‐oxo‐3‐phenylpropyl)‐1,2,5,6‐tetrahydropyridine derivatives 1a–p in strong acids to give 4,6‐diphenylsubstituted 1‐azabicyclo[3.3.1]nonadienes 2a–p. Some qualitative observations were made on substituents and reaction conditions influencing the ring closure reaction. Naphthylsubstituted starting compounds 3a, b were converted into pentacyclic compounds 4a, b which represent a new ring system, suggesting the occurrence of a carbenium ion intermediate in the ring closure reaction. Some of the compounds 2a–p show remarkable antifungal and antibacterial effects. magnified image