Synthesis of two unnatural oxygenated aaptaminoids

J Org Chem. 2012 Nov 16;77(22):10461-7. doi: 10.1021/jo3020598. Epub 2012 Oct 31.

Abstract

Two unprecedented oxygenated aaptaminoids have been synthesized starting from cheap and easily available 2,3-dihydroxybenzoic acid with the satisfactory overall yields of 31% and 34%. The key step of the procedure is the divergent thermic 5-exodig vs base-promoted 6-endodig cyclization of a 5-alkynylquinolinone derivative.

MeSH terms

  • Alkynes / chemistry*
  • Cyclization
  • Hydroxybenzoates / chemistry*
  • Molecular Structure
  • Naphthyridines / chemical synthesis*
  • Naphthyridines / chemistry*
  • Oxygen / chemistry*
  • Quinolones / chemistry*
  • Stereoisomerism

Substances

  • Alkynes
  • Hydroxybenzoates
  • Naphthyridines
  • Quinolones
  • 2,3-dihydroxybenzoic acid
  • aaptamine
  • Oxygen