Regioselectivity and tautomerism of novel five-membered ring nitrogen heterocycles formed via cyclocondensation of acylthiosemicarbazides

Abstract

A series of 1-acyl-4-phenyl/(acridin-9-yl)thiosemicarbazides 3, including four new compounds, were prepared in order to study substituent effects on cyclization reactions with oxalyl chloride (producing imidazolidine-4,5-diones 4), dimethyl acetylenedicarboxylate (to give thiazolidin-4-ones 7 and 8) and autocondensation under alkaline conditions (to yield 1,2,4-triazoles 9). A positional isomer, 10 of compound 3f was also prepared. Altogether, twenty new compounds characterized and identified by IR, UV, 1H, 13C and 2D NMR and quantum chemical calculations are described. The tautomerism of 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 cell line and all compounds, except for 3f, exhibited promising inhibitions of cell growth. © 2008 by MDPI.