Synthesis of some trifluoromethyl substituted 1-methylpyrazoles
โ Scribed by James W. Pavlik; Theppawut Israsena Na Ayudhya; Supawan Tantayanon
- Book ID
- 102341919
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2003
- Tongue
- English
- Weight
- 33 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0022-152X
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โฆ Synopsis
Abstract
The major products from the reaction of ฮฒโalkoxyvinyl trifluoromethyl ketones 1aโc with methylhydrazine (2) in absolute ethanol are the 3โ(trifluoromethyl)โsubstitutedโ1โmethylpyrazoles 3aโ3c with lesser amounts of the 5โ(trifluoromethyl)โsubstituted products 4aโ4c and 5aโ5c. Carrying out the reaction in nonโpolar, aprotic solvents can further enhance the regioselectivity favoring the 3โ (trifluoromethyl) โsubstituted isomers.
๐ SIMILAR VOLUMES
Trifluoromethyl substitution on the pyrazole ring was found to enhance photoreactivity via the P 4 pathway which involves interchange of the N2-C3 ring atoms. Thus, 1-methyl-3-(trifluoromethyl)pyrazole (1) and 1methyl-5-(trifluoromethyl)pyrazole (3) transposed with a P 4 /P 6 or P 4 /P 6 +P 7 ratio