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

Authors
Alajarin, M Vidal, A Sanchez-Andrada, P Tovar, F Ochoa, G
Citation
M. Alajarin et al., Conversion of N-acyl-4-acyloxy-beta-lactams into 1,3-oxazin-6-ones: Two consecutive pseudopericyclic processes, ORG LETT, 2(7), 2000, pp. 965-968
Citations number
27
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
7
Year of publication
2000
Pages
965 - 968
Database
ISI
SICI code
1523-7060(20000406)2:7<965:CONI1T>2.0.ZU;2-R
Abstract
[GRAPHICS] N-Acyl-4-acyloxy-beta-lactams are converted into 1,3-oxazin-6-ones under ba sic conditions. This transformation is believed to proceed via N-acylazeton es, which rearrange to the final products by a sequence of two electrocycli c processes. The calculated (RHF and B3LYP) transition structures of both c oncerted reactions are shown to present characteristic pseudopericyclic orb ital topologies.