Synthesis of γ-Unsaturated Enamides byN-Acylation of Imines Derived from γ-Unsaturated Amines

✍ Scribed by Meuzelaar, Gerrit J. ;Van Vliet, Michiel C. A. ;Neeleman, Ernst ;Maat, Leendert ;Sheldon, Roger A.

• Book ID: 102902517
• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 549 KB
• Volume: 1997
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199719970617

✦ Synopsis

Abstract

N‐Formyl‐N‐styryl amines (1–3) were prepared from imines derived from γ‐unsaturated amines and phenylacetaldehyde by formylation with ethyl formate in the presence of sodium methoxide. Formation of the corresponding N‐acetyl analogues was less selective, as was demonstrated by reaction of N‐[2‐(cyclohexen‐1‐yl)ethyl]‐2‐(phenyl)ethylidenimine and acetyl chloride. Some N‐acetyl‐N‐vinyl amines (7, 11) were prepared from the corresponding imines by acetylation with acetyl chloride or acetic anhydride. N‐Formyl‐N‐vinyl amines (12, 13) were synthesized from the appropriate imines using acetic formic anhydride as formylating agent.