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Heterocycles: 2 —Regiospecific addition of methylhydrazine to acetylenic ketones
Author(s) -
ElRayyes N. R.,
Hovakeemian G. H.,
Hammoud H.
Publication year - 1983
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/omr.1270210404
Subject(s) - methylhydrazine , chemistry , medicinal chemistry , organic chemistry , phenylhydrazine
The reaction of 1‐ p ‐methoxyphenyl‐3‐phenyl‐2‐propen‐1‐one and 3‐ p ‐methoxyphenyl‐1‐phenyl‐2‐propen‐1‐one with methylhydrazine gave 1‐methyl‐3‐ p ‐methoxyphenyl‐5‐phenylpyrazoline and 1‐methyl‐3‐phenyl‐5‐ p ‐methoxyphenylpyrazoline, respectively. These compounds, on oxidation, gave 1‐methyl‐3‐ p ‐methoxyphenyl‐5‐phenylpyrazole(2) and 1‐methyl‐3‐phenyl‐5‐ p ‐methoxyphenylpyrazole, respectively. When methyl‐hydrazine was made to react with 1‐ p ‐methoxyphenyl‐3‐phenyl‐2‐propyn‐1‐one, a pyrazole was obtained which proved to be identical with 2. Confirmatory evidence for this identity was obtained from their spectral data.