1. Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs
- Author
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Raquel Román, Juan F. Sanz-Cervera, Salvador Villanova, Santos Fustero, Ana C. Cuñat, Marcelo Murguia, and Antonio Simón-Fuentes
- Subjects
Methylhydrazine ,FLUORINATED PYRAZOL ,Fluorine Compounds ,Alcohol ,Pyrazole ,Methylation ,Chemical synthesis ,PYRAZOL ,chemistry.chemical_compound ,Animals ,Organic chemistry ,Acari ,Diketone ,Tebufenpyrad ,Molecular Structure ,Chemistry ,Organic Chemistry ,Ciencias Químicas ,Regioselectivity ,Stereoisomerism ,FLUOROUS ,Phenylhydrazines ,Solvent ,Química Orgánica ,Alcohols ,Solvents ,Pyrazoles ,TEBUFENPYRAD ,CIENCIAS NATURALES Y EXACTAS - Abstract
The preparation of N-methylpyrazoles is usually accomplished through reaction of a suitable 1,3-diketone with methylhydrazine in ethanol as the solvent. This strategy, however, leads to the formation of regioisomeric mixtures of N-methylpyrazoles, which sometimes are difficult to separate. We have determined that the use of fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation, and we have used this modification in a straightforward synthesis of fluorinated analogs of Tebufenpyrad with acaricide activity. Fil: Fustero, Santos. Universidad de Valencia; España Fil: Roman, Raquel. Universidad de Valencia; España Fil: Sanz Cervera, Juan F.. Universidad de Valencia; España. Centro de Investigaciones Principe Felipe; España Fil: Simon Fuentes, Antonio. Universidad de Valencia; España Fil: Cuñat, Ana. Universidad de Valencia; España Fil: Villanova, Salvador. Universidad de Valencia; España Fil: Murguia, Marcelo Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
- Published
- 2008