Reactions of 9-Alkyl-3-aminocarbazoles with Ethyl-3-oxo-butanoate and Identification of the Products Obtained 英文参考文献.docVIP

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Reactions of 9-Alkyl-3-aminocarbazoles with Ethyl-3-oxo-butanoate and Identification of the Products Obtained 英文参考文献.doc

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Reactions of 9-Alkyl-3-aminocarbazoles with Ethyl-3-oxo-butanoate and Identification of the Products Obtained 英文参考文献

Molecules 2006, 11, 72–80 molecules ISSN 1420-3049 Reactions of 9-Alkyl-3-aminocarbazoles with Ethyl-3-oxo- butanoate and Identification of the Products Obtained Birute Sapijanskaite 1, Vytautas Mickevicius 1,? and Gema Mikulskiene 2,* 1 Department of Organic Chemistry, Kaunas University of Technology, Radvilenu pl. 19, LT-50254 Kaunas, Lithuania, Tel.: (+370) 37 456 561, Fax: (+370) 37 300 152, ? E-mail: vytautas.mickevicius@ktu.lt 2 Institute of Biochemistry, LT-08662 Vilnius, Mokslininku 12, Lithuania, Tel.: (+370) 5 272 9195, Fax: (+370) 5 272 9196 *Author to whom correspondence should be addressed; E-mail: gemam@bchi.lt Received: 17 March 2005; in revised form: 19 October 2005 / Accepted: 20 October 2005 / Published: 31 January 2006 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 °C. The structures of the synthesized compounds were investigated by IR, mass spectrometry, 1H- and 13C-NMR spectroscopy and MM2 molecular mechanics and AM1 semi-empirical quantum mechanical methods. Keywords: Condensation, intramolecular cyclization, substituted pyrido[2,3-c]carbazol-1- ones, NMR spectra, molecular modeling. Introduction We have chosen to study the synthesis of carbazole ring-containing amino acids and their derivatives for two main reasons: carbazole fragments are present in the structure of some alkaloids [1- 3] and carbazole ring-containing compounds usually exhibit semiconductor properties and are used in electrography [4,5]. It was also expected that their combination with amino acid fragments would enable the synthesis of new biologically active substances. Molecules