Reaction of α-keto hydrazonyl bromide with carbanions of some active methylene compounds

Treatment of 1-phenyl-2-bromo-2-arylhydrazonoethanone (VII) with sodium etiolates of 2,4-pentanedione, 1-phenyl-1,3-butanedione, dibenzoylmethane, ethyl benzoylacetate, acetoaceta-nilide, and of benzoylacetanilide in ethanol afforded the substituted pyrazoles, VIII-XIII, respectively. The results show that VII, unlike 1-phenyl-2-bromo-2-hydroximinoethanone (V), is not easily deprotonated by carbanions; and that its reactions with β-diketones, β-keto esters, and β-keto amides follow one and the same mechanism. The structures of the products (VIII-XIII) were inferred from their elemental analyses and spectral data.