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Reaction of Schiff bases with thioglycolic acid was set up with Dean stark apparatus in toluene. The Schiff bases containing aniline derivatives 1a and 2a gave thiazolidin-4-one containing compounds 1b and 2b only; 1-naphthyl amine gave a mixture of thiazolidin-4-one ( 3b) and thiazepin-1(2H)-one ( 3b’ ) containing compounds; 2-naphthyl amine ( 4a ) gave and thiazepin-1(2H)-one containing compound 4b . The yields of reaction were moderate to high. The structures of these compounds were elucidated by 1 H and 13 C NMR and mass spectral analysis. Biological test results showed that Schiff base 4a was not active on any bacteria. Thiazolidine-4-one compound 1b was not active on bacteria and fungi, but was active against KB with IC 50 21.33 (mg/mL). Thiazepine compound 4b exhibited activity on Staphyloccccus aureus bacterium at IC 50 64.00 (mg/mL) and cancer cell line KB at IC 50 11.52 (mg/mL).

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