Preparation of novel selenapenams and selenacephems by nucleophilic and radical chemistry involving benzyl selenides

Org Biomol Chem. 2004 Sep 21;2(18):2612-8. doi: 10.1039/B409242B. Epub 2004 Aug 20.

Abstract

2,2a-Dihydro-1H,8H-azeto[2,1-b][1,3]benzoselenazin-1-one (12), 5-selena-1-azabicyclo[4.2.0]oct-3-en-8-one (13), ethyl 1-aza-7-oxo-4-selenabicyclo[3.2.0]heptane-2-carboxylate (16), and benzoselenopenem (33) can be prepared in 39-85% yield through the intramolecular homolytic substitution of aryl, vinyl or alkyl radicals at the selenium atom in suitably-substituted 4-benzylseleno-beta-lactams, or through intramolecular nucleophilic substitution by the benzylseleno moiety in 4-halo-beta-lactam precursors. Application of this chemistry to the preparation of optically active selenium-containing analogues of beta-lactam antibiotics is also detailed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Benzyl Compounds / chemistry*
  • Molecular Structure
  • Organoselenium Compounds / chemical synthesis*
  • Organoselenium Compounds / chemistry
  • beta-Lactams / chemistry*

Substances

  • Anti-Bacterial Agents
  • Benzyl Compounds
  • Organoselenium Compounds
  • beta-Lactams