255395-92-7Relevant articles and documents
Amino-Claisen rearrangements and Diels-Alder reactions of ketene N,O-acetals: Reactivity studies. On the way to a novel tandem process?
Neuschuetz, Klaus,Simone, Jean-Mary,Thyrann, Thomas,Neier, Reinhard
, p. 2712 - 2737 (2007/10/03)
We report the synthesis of N-benzyl-N-[(E)-buta-1,3-dienyl]propanamide (6) and its corresponding O-silyl-substituted ketene N,O-acetal 7 and their Diels-Alder reaction. Propanamide 6 reacted smoothly, whereas the yield obtained from 7 was low, probably due to polymerization of the dienophile induced by electron transfer. The ketene N,O-acetals 27a-g were synthesized starting from the corresponding benzamides 25a-e (Scheme g). The ketene N,O-acetals 27a-g showed increased stabilities and underwent amino-Claisen rearrangements under thermal conditions. Using catalysts, interesting side reactions leading either to the annulated systems rac-35-37 or to a β-lactam rac-34 were observed.