A new route to multifunctionalized p-terphenyls and heteroaryl analogues via [5C + 1C(N)] annulation strategy

J Org Chem. 2009 Jan 16;74(2):899-902. doi: 10.1021/jo802318p.

Abstract

p-Terphenyls and heteroaryl analogues including bipyridines were prepared via [5C + 1C(N)] annulation of alpha-aryl-alpha-alkenoyl ketene-(S,S)-acetals (five carbon 1,5-bielectrophilic species) with nitroethane or ammonium acetate. The reaction features mild conditions, multisubstitution, and functional group tolerance and is metal catalyst free. The present protocol provides a new alternative to the conventional methodologies for the synthesis of teraryls.

MeSH terms

  • Aldehydes / chemistry
  • Carbon / chemistry*
  • Nitrogen / chemistry*
  • Terphenyl Compounds / chemistry*

Substances

  • Aldehydes
  • Terphenyl Compounds
  • Carbon
  • 3-hydroxybutanal
  • Nitrogen