SYNTHESIS OF BISPIROHETEROCYCLIC SYSTEMS AS ANTIMICROBIAL AGENTS VIA THE REACTION OF YCLOALKYLIDENE)-1-THIA-4-AZASPIRO[4.4]-NONAN-3-ONE ANDOR [4.5]DECAN-3-ONE WITH HYDRAZINES, HYDROXYLAMINE, UREA AND THIOUREADERIVATIVES/

1-Oxa-4-thiaspiro [4.4]nonan-2-one (1) and/or 1-oxa-4-thiaspiro[4.5]-d ecan-2-one (2) reacted with 1-naphthylamine to afford 1-thia-4-(1-naph thyl)-4-azaspiro[4.4]nonan-3-one (3) and/or 1-thia-4-(-naphthyl)-4-aza spiro[4.5]decan-3-one (4). Reactions of 3 and/or 4 with cyclopentanone or cyclohexanone gave the corresponding -4-(1-naphthyl)-1-thia-4-azas piro[4.4]nonan-3-ones (5 and 6) and -cycloalkylidene-4-(1-naphthyl)-1- thiadecan-3-ones (7 and 8). Reaction of compounds 5-8 with hydrazine h ydrate, phenylhydrazine, hydroxylamine hydrochloride, urea and thioure a afforded the corresponding bispirothiazolopyrazolines (9-16), bispir othiazoloisoxazolines (17-20), bispirothiazolopyrimidinones (21-24) an d bispirothiazolothiopyrimidinones (25-28) respectively. All the synth esized bispiroheterocyclic derivatives were identified by conventional methods (IR, H-1-NMR) and elemental analyses. All the prepared compou nds were tested for their antimicrobial activities in comparison with tetracycline as a reference compound.