Interaction of α,β-unsaturated ketones of the adamantane series with N,N'-binucleophiles

The influence has been established of the structure of the initial ketone, the reactants, and the reaction conditions on the direction of the interaction of α,β-unsaturated ketones of the adamantane series with hydrazine, phenylhydrazine, semicarbazide, thiosemicarbazide, urea, and thiourea. It was found that on interaction with hydrazine and phenylhydrazine both intermediate hydrazones and the final cyclization products, pyrazolines, were formed. Reaction with semicarbazide and thiosemicarbazide leads only to the synthesis of derivatives at the carbonyl group, semicarbazones and thiosemicarbazones, but with urea and thiourea leads to products of addition at the double bond.