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2. A Convenient Conversion of Pyrazolyl Disulfide to Sulfides by Sodium Dithionite and Synthesis of Sulfoxides

Author

Qiu-Lian Lin, Ri-Yuan Tang, and Ping Zhong

Subjects
chemistry.chemical_classification, Chemistry, Organic Chemistry, Disulfide bond, Halide, General Medicine, Pyrazole, Ring (chemistry), Biochemistry, Medicinal chemistry, Inorganic Chemistry, Sodium dithionite, chemistry.chemical_compound, Environmental Chemistry, Organic chemistry, Physical and Theoretical Chemistry, Trichloroisocyanuric acid, Alkyl, Fipronil
Abstract

Indirectly introduce trifluoromethylthio-, alkylthio-, and trifluoromethylsulfinyl to pyrazole ring by a convenient reaction of a pyrazolyl disulfide with F3CBr and alkyl halides in the presence of sodium dithionite at room temperature. Followed by selective oxidation with H2O2 or trichloroisocyanuric acid (TCCA) to give trifluoromethylsulfenyl phenylpyrazole, alkylsulfenyl phenylpyazole, trifluoromethylsulfinyl phenylpyrazole 4a (a highly efficient insecticide named fipronil) and ethylsulfinyl phenylpyrazole 4c derivatives, respectively.

Published
2006

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