
Tetrahedron Letters p. 6269 - 6272 (2003)
Update date:2022-08-03
Topics:
Cainelli, Gianfranco
Giacomini, Daria
Gazzano, Massimo
Galletti, Paola
Quintavalla, Arianna
This paper describes the different reactivity of E- and Z-4-alkylidene-β-lactams in acylation reactions under basic conditions. The E isomer is readily acylated, whereas the Z reacted sluggishly rearranging to the corresponding oxazin-6-one. The N-acylation of Z isomers was successfully obtained with oxalyl- or malonyl chlorides in benzene at reflux.
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