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Abstract
AbstractBromination of 1‐arylsulfonyl‐1,2‐propanedione‐1‐aryl‐hydrazones 7 in a mixture of acetic acid and acetic anhydride in the presence of sodium acetate gave N‐aryl‐C‐arylsulfonylformohydrazidoyl bromides 5. Treatment of 5 with dibenzoylmethane, acetylacetone, ethyl acetoacetate and ethyl benzoylacetate in ethanol in the presence of sodium ethoxide yielded the pyrazole derivatives 8‐11, respectively. Reaction of 5 with potassium thiocyanate afforded the thiadiazoline derivative 14. The bromides 5 also react with nucleophiles such as morpholine, piperidine, phenoxide, thiophenoxide and benzenesulfinate anions to give the corresponding substitution products 19‐23, respectively. The structures of the products 8‐23 were assigned and confirmed on the basis of their spectral and elemental analyses, their chemical behaviour and alternate synthesis wherever possible.
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