Synthesis of trifluoromethyl-substituted 1,2,6-thiadiazine 1-oxides from sulfonimidamides under mechanochemical conditions

TBS-protected or NH-sulfonimidamides react with beta-alkoxyvinyl trifluoromethylketones under solvent-free mechanochemical conditions to give 3-trifluoromethyl-substituted three-dimensional 1,2,6-thiadiazine 1-oxides. C4-Functionalized products can be obtained by starting from cyclic enones and brominations of the initially formed heterocycles. The stability of the products was investigated by varying the pH value and storage under aerobic conditions.

Automated summary

In this study, TBS-protected or NH-sulfonimidamides were reacted with beta-alkoxyvinyl trifluoromethylketones under solvent-free mechanochemical conditions to produce 3-trifluoromethyl-substituted three-dimensional 1,2,6-thiadiazine 1-oxides. C4-functionalized products were obtained by starting from cyclic enones and brominations of the initially formed heterocycles. The stability of the products was investigated by varying the pH value and storage under aerobic conditions.