Vinyl azides derived from allenes: thermolysis leading to multisubstituted 1,4-pyrazines and Mn(III)-catalyzed photochemical reaction leading to pyrroles

J Org Chem. 2012 Oct 5;77(19):8712-22. doi: 10.1021/jo301694n. Epub 2012 Sep 24.

Abstract

Thermolysis of phosphorus-based vinyl azides under solvent- and catalyst-free conditions furnished a new route for 1,4-pyrazines. A simple one-pot, Mn(III)-catalyzed photochemical route has been developed for multisubstituted pyrroles starting from allenes and 1,3-dicarbonyls via in situ-generated vinyl azides. The utility of new phosphorus-based pyrroles is also demonstrated in the Horner reaction. The structures of key products are unequivocally confirmed by X-ray crystallography.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides / chemistry*
  • Catalysis
  • Crystallography, X-Ray
  • Manganese / chemistry*
  • Molecular Structure
  • Photochemical Processes
  • Pyrazines
  • Pyrroles / chemistry*
  • Vinyl Compounds / chemistry*

Substances

  • Azides
  • Pyrazines
  • Pyrroles
  • Vinyl Compounds
  • Manganese