Synthetic Organic Chemistry Laboratory, Department of Chemistry, M. L. Sukhadia University, Udaipur-313 001, Rajasthan, India E-mail : gtalesara@yahoo.com Manuscript received 15 December 2008, revised 15 May 2009, accepted 26 June 2009 Reaction of acetylacetone with hydrazine hydrate gave 3,5-dimethyl-1H-pyrazole (1) which when reacted with ethylchloroacetate in acetone and thiosemicarbazide yielded ethyl-3,5-dimethyl-1H-pyrazol-l-yl-acetate (2) and 2-[(3,Sdimethyl-1H-pyrazol-1-yl)acetyl]hydrazine carbothioamide (3) respectively. Compound 3 acted as a key intermediate for both the series of final compounds. In one pathway, it was converted to corresponding thiadiazole (11) by treatment with cone. H2SO4 and NH3 which on condensation with co-bromoethoxyphthalimide (10) gave 5-[(3,5-dimethyl-1H-pyrazoll-yl)methyl]-N-ethoxyphthalimido-1,3,4-thiadiazol-2-amine (12). In another pathway, 3 reacted with chloroacetic acid to furnish 2-[(3,5-dimethyl-1H-pyrazolyl)-4-oxo-1,3-thiazolidin-2-ylidene acetohydrazide (4). Reaction of 4 with various araldehydes (5a-d) gave 5-[(4-substituted phenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene)-2-[(3,5-dimethyl-1H-pyrazolyl)acetohydrazide (6a-d) which were further treated in two alternate routes. Firstly, with 10 to yield 5-{[(4- substituted phenyI) methyIidene)-3-N -ethoxyph thalimido -4-oxo-1, 3-thiazoli din-2-y lidene}-2-(3, 5-dimethyl-1H-pyrazolyl)acetohydrazide (8a-d). Cyclisation of these derivatives using hydroxylamine hydrochloride produced the target compounds 3-(4-substituted phenyl)-6-N-ethoxyphthalimido-3,3a-dihydro[1,3)thiazolo[4,5-c)isoxazoi-5(6H)-ylidene-2-(3,Sdimethyi-1H-pyrazol-1-yl)acetohydrazide (9a-d). In parallel, 6a-d were first cyclised with hydroxylamine hydrochloride to give 3-[( 4-substituted phenyl)-3,3a-dihydro[1 ,3] thiazolo [ 4,5-c ]isoxazoi-5(6H)-ylidene-2-(3,5-dimethyl-1H -pyrazol-1- yl)acetohydrazide (7a-d) and then condensed with 10 to yield the final compounds 9a-d. Structural elucidation of synthesized compounds was accomplished by IR, 1H NMR, 13C NMR and mass spectral data. Final compounds were screenedfor their antimicrobial activity.