Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs

6533b82efe1ef96bd1293ce1

RESEARCH PRODUCT

Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs

Raquel Román Juan F. Sanz-cervera Salvador Villanova Santos Fustero Ana C. Cuñat Marcelo Murguia Antonio Simón-fuentes

subject

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

description

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

year	journal	country	edition	language
2008-01-01	The Journal of Organic Chemistry

https://doi.org/10.1021/jo800251g

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