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Molecules 2006, 11(1), 72-80; https://doi.org/10.3390/11010072

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

1
Department of Organic Chemistry, Kaunas University of Technology, Radvilenu pl. 19, LT-50254 Kaunas, Lithuania
2
Institute of Biochemistry, LT-08662 Vilnius, Mokslininku 12, Lithuania
*
Author to whom correspondence should be addressed.
Received: 17 March 2005 / Revised: 19 October 2005 / Accepted: 20 October 2005 / Published: 31 January 2006
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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. View Full-Text
Keywords: Condensation; intramolecular cyclization; substituted pyrido[2; 3-c]carbazol-1- ones; NMR spectra; molecular modeling. Condensation; intramolecular cyclization; substituted pyrido[2; 3-c]carbazol-1- ones; NMR spectra; molecular modeling.
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Sapijanskaite, B.; Mickevicius, Y.; Mikulskiene, G. Reactions of 9-Alkyl-3-aminocarbazoles with Ethyl-3-oxo-butanoate and Identification of the Products Obtained. Molecules 2006, 11, 72-80.

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