title: Synthesis of N-acyl-5-aminopenta-2,4-dienals via base-induced ring-opening of N-acylated furfurylamines: scope and limitations.
abstract: 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.
authors.affiliation: Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.
authors.forename: Cécile
authors.initials: C
authors.lastname: Ouairy
authors.forename: Patrick
authors.initials: P
authors.lastname: Michel
authors.forename: Bernard
authors.initials: B
authors.lastname: Delpech
authors.forename: David
authors.initials: D
authors.lastname: Crich
authors.forename: Christian
authors.initials: C
authors.lastname: Marazano
mesh_terms: D000215:Acylation; D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D005663:Furans; C439622:furfurylamine; D009584:Nitrogen