Synthesis of N-acyl-5-aminopenta-2,4-dienals via base-induced ring-opening of N-acylated furfurylamines: scope and limitations.

Cécile Ouairy, Patrick Michel, Bernard Delpech, David Crich, Christian Marazano

Index: J. Org. Chem. 75(12) , 4311-4, (2010)

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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.