One-pot synthesis of cyclic triamides with a triangular cavity from trans-stilbene and diphenylacetylene monomers

Org Lett. 2008 Aug 7;10(15):3207-10. doi: 10.1021/ol801083r. Epub 2008 Jun 27.

Abstract

Base-promoted self-condensation reactions of trans-stilbene and diphenylacetylene monomers bearing 4-alkylamino and 4'-methoxycarbonyl groups were investigated. Reactions of N-propyl monomers under pseudohigh-dilution conditions (a THF solution of monomer was added dropwise to a THF solution of LiHMDS) afforded the corresponding cyclic triamides in good yields. X-ray crystallographic analysis showed that these cyclic triamides possessed an almost equilateral triangle structure with a cavity surrounded by tilted benzene rings.

MeSH terms

  • Acetylene / analogs & derivatives*
  • Acetylene / chemistry
  • Amides / chemical synthesis*
  • Amides / chemistry
  • Crystallography, X-Ray
  • Cyclization
  • Models, Molecular
  • Stilbenes / chemistry*

Substances

  • Amides
  • Stilbenes
  • biphenylacetylene
  • Acetylene