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Authors = Ivan Danihel

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18 pages, 121 KiB  
Article
Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides
by Jana Tomaščiková, Ján Imrich, Ivan Danihel, Stanislav Böhm, Pavol Kristian, Jana Pisarčíková, Marián Sabol and Karel D. Klika
Molecules 2008, 13(3), 501-518; https://doi.org/10.3390/molecules13030501 - 1 Mar 2008
Cited by 29 | Viewed by 12162
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 [...] Read more.
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. Full article
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