Facile one-pot synthesis of 5-aryl/heterylidene-2-(2-hydroxyethyl- and 3-hydroxypropylamino)-thiazol-4-ones via catalytic aminolysis

<p>A multicomponent synthetic approach for 5-aryl/heterylidene-2-(2-hydroxyethylamino)- and 2-(3-hydroxypropylamino)-thiazol-4-ones starting from 2-thioxothiazolidin-4-one or 2-methylsulfanylthiazol-4-one was developed. The proposed method involves simultaneous aminolysis of 2-thioxo- or 2-methylsulfanyl groups and Knoevenagel condensation with (hetero)aromatic aldehydes using 2-aminoethanol or 3-aminopropan-1-ol as catalysts. Side-chain prototropic amino–imino tautomerism was observed for target 5-ylidene-2-alkylaminothiazol-4-ones.</p

The application of anthraquinone-based triazenes as equivalents of diazonium salts in reaction with methylene active compounds

<p></p> <p>A series of polyfunctionalized anthraquinonehydrazones have been prepared using azo-coupling reaction between anthraquinone-based triazenes and methylene active compounds in acetic acid without a catalyst. The structures of new synthesized compounds were confirmed by their IR, LCMS,¹H and ¹³C NMR spectroscopic data. Some of the synthesized compounds were screened for their <i>in vitro</i> anticancer activity according to US NCI protocols. Biological screening data led to the identification of 1-{N’-[3-(4-hydroxyphenyl)-4-oxo-2-thioxothiazolidin-5-ylidene]hydrazino}anthraquinone <b>3.4</b> as having antitumor activity on the non-small cell lung cancer NCI-H460 (GP = 13.25%) and colon cancer HCT-116 (GP = 13.69%) cell lines.</p