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

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) an...

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Bibliographic Details
Main Authors: Karel D. Klika, Marián Sabol, Jana PisarÄÂíková, Pavol Kristian, Stanislav Böhm, Ivan Danihel, Ján Imrich, Jana TomaÅ¡ÄÂiková
Format: Article
Language:English
Published: MDPI AG 2008-03-01
Series:Molecules
Subjects:
1
2
Online Access:http://www.mdpi.com/1420-3049/13/3/501/
Description
Summary: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.
ISSN:1420-3049