Allylic amination and N-arylation-based domino reactions providing rapid three-component strategies to fused pyrroles with different substituted patterns

J Org Chem. 2012 Sep 7;77(17):7497-505. doi: 10.1021/jo301323r. Epub 2012 Aug 13.

Abstract

New three-component domino reaction providing divergent approaches to multifunctionalized fused pyrroles with different substituted patterns have been established (40 examples). The direct C(sp(3))-N bond formation was achieved through intermolecular allylic amination in a one-pot operation, and N-arylation of amines was realized by varying N-amino acid enaminones. The reaction is easy to perform simply by mixing three common reactants in acetic acid under microwave heating. The reaction proceeds at fast rates and can be finished within 30 min, which makes workup convenient to give good chemical yields.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Allyl Compounds / chemistry*
  • Amination
  • Molecular Structure
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry

Substances

  • Allyl Compounds
  • Pyrroles