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Synthesis of γ‐Unsaturated Enamides by N ‐Acylation of Imines Derived from γ‐Unsaturated Amines
Author(s) -
Meuzelaar Gerrit J.,
Van Vliet Michiel C. A.,
Neeleman Ernst,
Maat Leendert,
Sheldon Roger A.
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970617
Subject(s) - chemistry , acetic anhydride , acylation , acetyl chloride , formylation , phenylacetaldehyde , organic chemistry , ethyl formate , formic acid , chloride , acetylation , sodium methoxide , medicinal chemistry , catalysis , biochemistry , gene
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.