𝔖 Bobbio Scriptorium
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Heterocycles: 2—Regiospecific addition of methylhydrazine to acetylenic ketones

✍ Scribed by N. R. El-Rayyes; G. H. Hovakeemian; H. Hammoud

Publisher
John Wiley and Sons
Year
1983
Tongue
English
Weight
238 KB
Volume
21
Category
Article
ISSN
0749-1581

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✦ Synopsis

The reaction of l-pmethoxyphenyl-3-phenyl-2-propen-l-one and 3-gmethoxyphenyl-l-phenyl-2-propen-lone with methylhydrazine gave 1-methyl-3-p-methoxyphenyl-S-phenylpyrazoline and l-methyl-3-phenyl-Sp-methoxyphenylpyrazoline, respectively. These compounds, on oxidation, gave 1-methyl-3-p-methoxyphenyl-5-phenylpyrazole(2) and l-methyl-3-phenyl-S-p-methoxyphenylpyrazoIe, respectively. When methylhydrazine was made to react with l-pmethoxyphenyl-3-phenyl-2-propyn-l-one, a pyrazole was obtained which proved to be identical with 2. Confirmatory evidence for this identity was obtained from their spectral data.

📜 SIMILAR VOLUMES

Intramolecular addition of alkyllithiums
Intramolecular addition of alkyllithiums to acetylenes: Regiospecific 4-, 5-, and 6-exo-dig cyclizations
✍ William F. Bailey; Timo V. Ovaska 📂 Article 📅 1990 🏛 Elsevier Science 🌐 French ⚖ 243 KB

Primary acetylenic alkylliihiums bearing a phenyl substiiueni on the triple bond, which may be prepared in virtually quantitative yield by low-temperature lithium-iodine interchange, undergo regiospecifii 8x0-dig cyclizatiin via stereoselective syn-addition of CHILi to the carbon-carbon triple bond