Molecules 2008, 13(3), 501-518; doi:10.3390/molecules13030501
Article

Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides

1, 1,* email, 1, 2, 1, 1, 3 and 4
Received: 19 February 2008; in revised form: 27 February 2008 / Accepted: 27 February 2008 / Published: 1 March 2008
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.


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