Alternative approaches to the synthesis of polyfluoroalkyl-containing 1-methyl-4-nitrosopyrazoles

• Published in: Russian chemical bulletin Vol. 70; no. 6; pp. 1135 - 1140
• Main Authors: Agafonova, N. A., Burgart, Ya. V., Gerasimova, N. A., Evstigneeva, N. P., Saloutin, V. I.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.06.2021; Springer Nature B.V
• Subjects: Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Diketones; Full Articles; Inorganic Chemistry; Methylhydrazine; Organic Chemistry; Reagents; Regioselectivity; Sodium nitrite; Synthesis; mycostatic activity; 1-methyl-4-nitrosopyrazoles; 4,4,4-trifluoro-3,3-dihydroxy-2-(hydroxyimino)butan-1-ones; polyfluoroalkyl-2-hydroxyimino-1,3-diketones
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-021-3195-2

We studied different approaches to the synthesis of polyfluoroalkyl-containing 1-methyl-4-nitrosopyrazoles, which are based on the cyclization of 4,4,4-trifluoro-3,3-dihydroxy-2-hydroxyimino-1-R-butan-1-ones or 2-hydroxyimino-1,3-diketones with methylhydrazine and on a one-pot sequential treatment of 1,3-diketones with sodium nitrite and methylhydrazine. It was found that the regioselectivity of the formation of 1-methyl-4-nitrosopyrazoles is affected by the steric factors of 1,3-dicarbonyl reagents. The study of the mycostatic effect of 4-nitrosopyrazoles showed that the introduction of a bulky polyfluoroalkyl or tert -butyl substituent leads to a decrease in their activity.