PERFLUOROALKYLATION OF 2-THIOPYRIMIDINE DERIVATIVES
Keywords:
4,6-dimethyl-2-perfluoroalkylthiopyrimidines, 4,6-dimethyl-5-trifluoromethyl-2-trifluoromethylthiopyrimidine, 4-methyl-6-(2,2,2-trifluoroethyl)-2-trifluoromethylthiopyrimidine, 2-perfluoroalkylthiopyrimidines, 4-trifluoromethyl-2-trifluoromethylthiopyrimidine, 4,5-bistrifluoromethyl-2-trifluoromethylthiopyrimidine, perfluoroalkylation of heterocyclic thiols and disulfidesAbstract
The method of perfluoroalkylation of heterocyclic thiols and disulfides by thermolytic reaction with xenon(II) bisperfluoroalkylcarboxylates has been extended to sulfur-containing pyrimidines, including 2-mercaptopyrimidines, symmetrical disulfides, and S-trifluoroacetyl derivatives obtained from the corresponding thiols. The main reaction products are 2-SCnF2n+1 (n = 1, 2)-substituted pyrimidines. Their formation proceeds only via disulfides into which the initial thiols and S-trifluoroacetyl derivatives are converted in the reaction medium. Side reactions occurred in the case of trifluoromethylation linked with the perfluoroalkylation of the pyrimidine nucleus at the free 5 position (in the case of the 4,6-dimethyl derivative), or at position 4 or 4 and 5 (for unsubstituted pyrimidine). In addition, the introduction of the CF3 group at one of the methyl substituents was confirmed by the formation of CH2CF3 fragment.
How to Cite
Sipyagin, A. M.; Enshov, V. S. Chem. Heterocycl. Compd. 2003, 39, 1172. [Khim. Geterotsikl. Soedin. 2003, 1336.]
For this article in the English edition, see DOI https://doi.org/10.1023/B:COHC.0000008261.59363.c0
