Conversion of N-acyl-4-acyloxy-beta-lactams into 1,3-oxazin-6-ones: two consecutive pseudopericyclic processes
N-Acyl-4-acyloxy-beta-lactams are converted into 1,3-oxazin-6-ones under basic conditions. This transformation is believed to proceed via N-acylazetones, which rearrange to the final products by a sequence of two electrocyclic processes. The calculated (RHF and B3LYP) transition structures of both concerted reactions are shown to present characteristic pseudopericyclic orbital topologies.
Alajarin
M
Departamento de Quimica Organica, Facultad de Quimica, Universidad de Murcia, Spain. alajarin@fcu.um.es
Vidal
A
Sanchez-Andrada
P
Tovar
F
Ochoa
G