REACTION OF SCHIFF BASES WITH THIOGLYCOLIC ACID: SYNTHESIS OF THIAZEPIN-1(2H)-ONE AND THIAZOLIDIN-4-ONE COMPOUNDS

Dương Quốc Hoàn
2018 HUE UNIVERSITY JOURNAL OF SCIENCE NATURAL SCIENCE  
<p>Reaction of Schiff bases with thioglycolic acid was set up with Dean stark apparatus in toluene. The Schiff bases containing aniline derivatives <strong>1a</strong> and <strong>2a</strong> gave thiazolidin-4-one containing compounds<strong> 1b</strong> and <strong>2b</strong> only; 1-naphthyl amine gave a mixture of thiazolidin-4-one (<strong>3b)</strong> and thiazepin-1(2H)-one (<strong>3b'</strong>) containing compounds; 2-naphthyl amine (<strong>4a</strong>) gave and thiazepin-1(2H)-one
more » ... ntaining compound <strong>4b</strong>. The yields of reaction were moderate to high. The structures of these compounds were elucidated by <sup>1</sup>H and <sup>13</sup>C NMR and mass spectral analysis. Biological test results showed that Schiff base<strong> 4a</strong> was not active on any bacteria. Thiazolidine-4-one compound <strong>1b</strong> was not active on bacteria and fungi, but was active against KB with IC<sub>50</sub> 21.33 (mg/mL). Thiazepine compound <strong>4b</strong> exhibited activity on Staphyloccccus aureus bacterium at IC<sub>50</sub> 64.00 (mg/mL) and cancer cell line KB at IC<sub>50</sub> 11.52 (mg/mL).</p><p> </p>
doi:10.26459/hueuni-jns.v127i1a.4516 fatcat:p37eyp555vg3pf6f4epuq2yypa