The Neber approach to 2-(tetrazol-5-yl)-2H-azirines

J Org Chem. 2013 Jul 19;78(14):6983-91. doi: 10.1021/jo4006552. Epub 2013 Jul 3.

Abstract

The synthesis of 2-(tetrazol-5-yl)-2H-azirines is reported for the first time. Using the Neber approach, β-ketoxime-1H-tetrazoles were converted into the target 2H-azirines bearing phenyl, furan-2-yl, thiophen-2-yl, or pyrrol-2-yl substituents at C-3. It was demonstrated that the alkaloid-mediated Neber reaction allows the asymmetric synthesis of 2-(tetrazol-5-yl)-2H-azirines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azirines / chemical synthesis*
  • Azirines / chemistry
  • Molecular Structure
  • Tetrazoles / chemical synthesis*
  • Tetrazoles / chemistry

Substances

  • Azirines
  • Tetrazoles