SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME 6-ARYLIDENE-3-ARYL-2,3,3a,4,5,6-HEXAHYDROCYCLOPENTA [c] PYRAZOLES/OXAZOLES

Condensation of alpha,alpha-bis (arylidene) cycloalkanones 1a,b with hydrazine hydrochloride in presence of gl acetic acid gave 6-arylidene-3-aryl-2,3,3a,4,5,6-hexahydrocyclopenta[e] pyrazoles 2a,b which on Mannich condensation with various alkyl and aryl amines yielded 2-aminomethyl-6-arylidene-3-aryl-2,3,3a,4,5,6-hexahydrocyclopenta[c] pyrazoles 5a-g. Condensation of 1 a,b with hydroxylamine hydrochloride in alcohol resulted in the formation of 6-arylidene-3-aryl-2,3,3a,4,5,6-hexahydrocyclopenta[c] oxazoles 4a,b. Further, compounds la,b undergo cyclization with phenylhydrazine hydrochloride/2,4-dinitro phenylhydrazine hydrochloride in presence of sodium acetate and gl acetic acid to furnish 2-(phenyl/2,4-dinitrophenyl)-6-arylidene-3-aryl-2,3,3a,4,5,6-hexahydrocyclopenta [c] pyrazoles 3a-d. The structures of the compounds have been established based on their analytical and spectral data. All the compounds have been evaluated in vitro for their antibacterial and antifungal activities. Compounds 2b, 5c and 5d exhibited significant antibacterial activity.