Reactions of 9-alkyl-3-aminocarbazoles with ethyl-3-oxo-butanoate and identification of the products obtained

Molecules. 2006 Jan 31;11(1):72-80. doi: 10.3390/11010072.

Abstract

The reactions in benzene of 9-alkyl-3-aminocarbazoles with ethyl-3-oxobutanoate yielded ethyl-3-[(9-alkyl-9H-carbazol-3-yl)amino]but-2-enoate condensation products or N-(9-ethyl-9H-carbazol-3-yl)-3-oxobutanamide acylation products. The condensation products were cyclized to the corresponding 4,7-dihydro-pyrido[2,3-c]-carbazol-1-ones upon heating in mineral oil at 240-250 degrees C. The structures of the synthesized compounds were investigated by IR, mass spectrometry, (1)H- and (13)C-NMR spectroscopy and MM2 molecular mechanics and AM1 semi-empirical quantum mechanical methods.

MeSH terms

  • Benzene / chemistry
  • Butyrates / chemistry*
  • Butyrates / metabolism*
  • Carbazoles / chemistry*
  • Carbazoles / metabolism*
  • Catalysis
  • Cyclization
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Magnetic Resonance Spectroscopy
  • Models, Biological
  • Models, Molecular

Substances

  • Butyrates
  • Carbazoles
  • Heterocyclic Compounds
  • Benzene