Reaction of acetylenic ketones with hydrazine derivatives. Synthesis of hydroxypyrazoles

Aroylphenylacetylenes Ia-c react with (-butyl hydrazinecarboxylate (IIa) and 2-furylhydrazide (IIb) to give the corresponding hydroxydihydropyrazole derivatives IVa-f. This cyclic structure is supported by chemical transformations. Thus, when compounds IVa-c are heated with acetic anhydride, they yield the corresponding 5-aryl-1-(t-butoxycarbonyl)-3-phenylpyrazoles Va-c which, upon hydrolysis with methanolic potassium hydroxide, produce the corresponding 5(3)aryl-3(5)phenylpyrazoles VI. Spectroscopic data also confirm the suggested cyclic structure IV.