Conversion of N-acyl-4-acyloxy-beta-lactams into 1,3-oxazin-6-ones: two consecutive pseudopericyclic processes

M Alajarin; A Vidal; P Sanchez-Andrada; F Tovar; G Ochoa

doi:10.1021/ol0056168

Conversion of N-acyl-4-acyloxy-beta-lactams into 1,3-oxazin-6-ones: two consecutive pseudopericyclic processes

Org Lett. 2000 Apr 6;2(7):965-8. doi: 10.1021/ol0056168.

Authors

M Alajarin¹, A Vidal, P Sanchez-Andrada, F Tovar, G Ochoa

Affiliation

¹ Departamento de Quimica Organica, Facultad de Quimica, Universidad de Murcia, Spain. [email protected]

PMID: 10768198
DOI: 10.1021/ol0056168

Abstract

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.