Reactions of 9-Alkyl-3-aminocarbazoles with Ethyl-3-oxo-butanoate and Identification of the Products Obtained

Abstract

The reactions in benzene of 9-alkyl-3-aminocarbazoles with ethyl-3-oxobutanoateyielded 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 productswere cyclized to the corresponding 4,7-dihydro-pyrido[2,3-c]-carbazol-1-ones upon heatingin mineral oil at 240-250 °C. The structures of the synthesized compounds were investigatedby IR, mass spectrometry, 1H- and 13C-NMR spectroscopy and MM2 molecular mechanicsand AM1 semi-empirical quantum mechanical methods.

Keywords

• Condensation
• intramolecular cyclization
• substituted pyrido[2
• 3-c]carbazol-1- ones
• NMR spectra
• molecular modeling.