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Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides
Institute of Chemistry, Faculty of Science, P. J. Šafárik University, SK-041 67 Košice, Slovak Republic
Department of Organic Chemistry, Institute of Chemical Technology, Prague, CZ-166 28 Prague 6, Czech Republic
Institute of Medical and Clinical Microbiology, Faculty of Medicine, P. J. Šafárik University, SK-040 66 Košice, Slovak Republic
Department of Chemistry, University of Turku, FIN-20014 Turku, Finland
* Author to whom correspondence should be addressed.
Received: 19 February 2008; in revised form: 27 February 2008 / Accepted: 27 February 2008 / Published: 1 March 2008
Abstract: A series of 1-acyl-4-phenyl/(acridin-9-yl)thiosemicarbazides 3, including fournew compounds, were prepared in order to study substituent effects on cyclizationreactions with oxalyl chloride (producing imidazolidine-4,5-diones 4), dimethylacetylenedicarboxylate (to give thiazolidin-4-ones 7 and 8) and autocondensation underalkaline conditions (to yield 1,2,4-triazoles 9). A positional isomer, 10 of compound 3f wasalso prepared. Altogether, twenty new compounds characterized and identified by IR, UV,1H, 13C and 2D NMR and quantum chemical calculations are described. The tautomerismof the products and regioselectivity of the reactions were evaluated. Compounds 3f−h,3h·2HCl, 7b,d and 10 were screened for cytotoxic activity against the L1210 leukemia cellline and all compounds, except for 3f, exhibited promising inhibitions of cell growth.
Keywords: Acylthiosemicarbazides; imidazolidine-4; 5-diones; thiazolidin-4-ones; 1; 2; 4-triazoles; acridines; cytotoxic activity.
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Tomaščiková, J.; Imrich, J.; Danihel, I.; Böhm, S.; Kristian, P.; Pisarčíková, J.; Sabol, M.; Klika, K.D. Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides. Molecules 2008, 13, 501-518.
Tomaščiková J, Imrich J, Danihel I, Böhm S, Kristian P, Pisarčíková J, Sabol M, Klika KD. Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides. Molecules. 2008; 13(3):501-518.
Tomaščiková, Jana; Imrich, Ján; Danihel, Ivan; Böhm, Stanislav; Kristian, Pavol; Pisarčíková, Jana; Sabol, Marián; Klika, Karel D. 2008. "Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides." Molecules 13, no. 3: 501-518.