164299-79-0Relevant 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.
Generalization of the Benzotriazole-Mediated Introduction of N-Substituents into Amides
Katritzky, Alan R.,Ignatchenko, Alexey V.,Lang, Hengyuan
, p. 4002 - 4005 (2007/10/02)
N-(Benzotriazol-1-ylmethyl) amides 2, easily available by condensation of BtCH2OH with amides, are used for the preparation of a variety of N-substituted amides such as the homoallyl, 1,3-butadienyl, and 2,2-diphenylcyclopropyl derivatives by displacement
