Cyclisation reactions of N-cinnamoyl-9-aminoanthracenes

Org Biomol Chem. 2014 May 28;12(20):3211-21. doi: 10.1039/c4ob00411f. Epub 2014 Apr 11.

Abstract

N-Cinnamoyl-9-aminoanthracenes cyclise with PPA or triflic acid to form novel 2-azahexacyclo[10.6.6.0(1,5).0(6,11).0(13,18).0(19,24)]tetracosa-6(11),7,9,13,15,17,19(24),20,22-nonaen-3-ones. In contrast, both N-cinnamoyl-N-methyl-9-(2-aminomethyl)anthracene and N-cinnamoyl-9-(2-aminoethyl)anthracene undergo an intramolecular Diels-Alder cycloaddition.

MeSH terms

  • Acids / chemistry
  • Anthracenes / chemical synthesis*
  • Anthracenes / chemistry
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Crystallography, X-Ray
  • Cyclization
  • Models, Molecular
  • Molecular Conformation
  • Proton Magnetic Resonance Spectroscopy
  • Quantum Theory

Substances

  • Acids
  • Anthracenes