Reactions of 9-alkyl-3-aminocarbazoles with ethyl-3-oxo-butanoate and identification of the products obtained.
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.
Sapijanskaite
Birute
B
Department of Organic Chemistry, Kaunas University of Technology, Radvilenu pl. 19, LT-50254 Kaunas, Lithuania.
Mickevicius
Ytautas
Y
Mikulskiene
Gema
G
D001554:Benzene / Q000737:chemistry; D002087:Butyrates / Q000737:chemistry* / Q000378:metabolism*; D002227:Carbazoles / Q000737:chemistry* / Q000378:metabolism*; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008954:Models, Biological; D008958:Models, Molecular
D002087:Butyrates; D002227:Carbazoles; D006571:Heterocyclic Compounds; D001554:Benzene