Journal
CHINESE JOURNAL OF ORGANIC CHEMISTRY
Volume 42, Issue 9, Pages 2832-2839Publisher
SCIENCE PRESS
DOI: 10.6023/cjoc202203051
Keywords
benzyne; [3+2] cycloaddition; benzocyclicsulfoximine; insecticidal activity
Categories
Funding
- Double First Class Project of Shihezi University [SHYL-YB201901]
- High Level Talents Launch Project of Shehezi University [RCZK2021B08]
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A concise and direct synthetic strategy for the construction of trifluoromethylated cyclic-sulfoximines has been developed through a [3 + 2] cycloaddition reaction. The reaction yields cyclosulfoximines in low to moderate yields at room temperature using KF as a fluorinated reagent, 18-C-6 as additives, and acetonitrile and toluene as a mixed solvent. The synthesized compounds exhibit lower insecticidal activities against Aphis gossypii.
Sulfoximines derivatives are widely used in the field of pesticides and medicine due to its antimalarial, antibacterial and herbicidal properties. A concise and direct synthetic strategy for the construction of trifluoromethylated cyclic-sulfoximines has been developed via [3 + 2] cycloaddition reaction of benzynes and trifluoromethyl alpha,beta-unsaturated N-(S)-tert-butyl sulfinylketoimines. The reaction affords the cyclosulfoximines at room temperature in low to moderate yields (13%similar to 57%) and KF as fluorinated reagent, 18-C-6 as additives, and acetonitrile and toluene as mixed solvent (V:V=4:1). The insecticidal activities against Aphis gossypii were determined by impregnation method. The results showed that 24-h median lethal concentrations (24 h LC50) of (1R,3S)-1-(tert-butyl)-3-((E)-4-methylstyryl)-3-(trifluoromethyl)-3H-1 lambda(4)-benzo-[d]isothiazole 1-oxide) (3b) and (1R,3S)-1-(tert-butyl)-3-(trifluoromethyl)-3-((E)-4-(trifluoromethyl)styryl)-3H-1 lambda(4)-benzo[d]isothiazole 1-oxide (3h) are lower than that of the positive control imidacolprid (0.0800 mg/L) and dinitraz (0.0532 mg/L). They can be used as new lead insecticidal compounds with further structure modification.
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