Domino approach for the synthesis of pyrrolo[1,2-alpha]pyrazine from vinyl azides

Org Lett. 2010 Sep 3;12(17):3863-5. doi: 10.1021/ol101538x.

Abstract

A domino synthesis of pyrrolo[1,2-alpha]pyrazine from 1H-2-pyrrolecarbaldehyde and readily synthesized vinyl azides was developed. This reaction proceeded under relatively mild conditions in the presence of base. Additionally, a possible mechanism for the entire sequence is proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Azides / chemistry*
  • Molecular Structure
  • Pyrazines / chemical synthesis*
  • Pyrazines / chemistry
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Stereoisomerism
  • Vinyl Compounds / chemistry*

Substances

  • Aldehydes
  • Azides
  • Pyrazines
  • Pyrroles
  • Vinyl Compounds