Synthesis of N-acyl-5-aminopenta-2,4-dienals via base-induced ring-opening of N-acylated furfurylamines: scope and limitations.
N-Acylation of furfurylamines provided 1, which on double deprotonation with LDA led to the formation of N-acyl-5-aminopenta-2,4-dienals 2 via an isomerization involving opening of the furan ring. The scope and limitations of the procedure were examined by considering the influence of substituents on the carbonyl group and also on the heterocycle moiety. The efficacy of the reaction was shown to be very dependent on the nature of these groups.
Ouairy
Cécile
C
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.
Michel
Patrick
P
Delpech
Bernard
B
Crich
David
D
Marazano
Christian
C
D000215:Acylation; D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*
D000447:Aldehydes; D005663:Furans; C439622:furfurylamine; D009584:Nitrogen