A. Haas, M. Lieb
Aug 1, 1985
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Journal
Journal of Fluorine Chemistry
Abstract
Abstract 5-Trifluoromethylthio-2,4(6)-tri(di)halogeno-substituted pyrimidines have been synthesized by reaction of 5-Tri- fluoromethylthiosubstituted uracile and barbituric acid with POX3 (X = Cl, Br). These pyrimidines are good starting materials for further nucleophilic exchange reactions; thus, 5-trifluoromethylthio-2,4(t)-tri(di)fluoro and 5-tri- fluoromethylthio-2,4(6)-tri(di)jodo compounds are synthesized by reaction with the corresponding alkali halides. In like manner alkoxy-, phenoxy-, anilino-, hydrazino- and amino-derivatives are formed. The latter derivatives can be substituted with Perhalogenomethylthio-functions ClnF3−nCS or converted into the isocyanates by reaction with oxalylchloride. Furthermore, CF3S-functions can be introduced into the pyrimidine ring by Grignard reactions or by using CuSCF3. Persubstituted CF3S- and CF3Se-pyrimidines are generated by reacting iodine-containing rings with Hg(SCF3)2 in the presence of an activated copper bronze.