Pyroglutamic acid smoothly reacts with sulfur tetrafluoride at room temperature to afford enantiomerically pure (5S)-5-(trifluoromethyl)pyrrolidin-2-one (92 % yield, Ͼ99 % ee).
Three isomers of C- (2,2,2-trifluoroethyl)aniline were prepared on a multigram scale from readily available nitrophenylacetic acids in two steps. First, the carboxy groups of the latter were converted into the trifluoromethyl moieties by treatment with sulfur tetrafluoride. The obtained 2,2,2-trifluoroethyl-substituted nitrobenzenes were reduced catalytically into the corresponding anilines.
New synthetic procedures for the trifluoromethyl-substituted triazoles, 3-(trifluoromethyl)-4H-1,2,4-triazole and 4-(trifluoromethyl)-1H-1,2,3-triazole, have been elaborated. The target compounds were prepared from commercially available trifluoroacethydrazide (one step) and methyl propiolate (three steps), respectively.
A convenient synthetic approach to previously unknown NH-iminophosphonates bearing 2-, 3-, and 4-pyridyldifluoromethyl groups at the imine carbon atom was developed. The synthetic potential of these novel building blocks was demonstrated by their conversion into highly functionalized acyclic and heterocyclic aminophosphonates and phosphonic acids combining in their structure biorelevant aminophosphonic fragment, difluoromethyl group, and pyridyl, piperidyl, thiazolidin-4-one, or thiazidinan-4-one heterocyclic moieties in a single molecular platform.
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