Phenyl-, p-chlorophenyl-, and 3,4-methylenedioxyphenyl-propiolic acids react with hydrazine to give, in each case, a mixture of the corresponding pyrazol-5-one and azine. p-Methoxyphenyl-, and 3,4-dimethoxyphenyl-propiolic acids give azines only. Phenyl-, p-chlorophenyl-, and m-chlorophenyl-propiolic acids react with phenylhydrazine to give the corresponding 5-aryl-1-phenylpyrazol-3-ones.
F. G. Baddar, M. F. El-Newaihy and M. R. Salem, J. Chem. Soc. C, 1969, 836 DOI: 10.1039/J39690000836
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