Synthesis of trifluoromethyl – containing oxo(thioxo)imidazothiazolones and thioglycolurils based on perfluorobiacetyl

[Display omitted] •4,5-Dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-thione was obtained through the reaction of perfluorobiacetyl with thiourea.•Trifluoromethylated thioxoimidazothiazolone was obtained by the condensation of the imidazolidine-2-thione with thiourea and NH4SCN.•Similar reactions of 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-one gave trifluoromethylated oxoimidazothiazolone.•The reaction of 4,5-bis(trifluoromethyl)imidazolidine-2-thione with N-substituted ureas yielded mainly the thioxoimidazothiazolone.•The condensation of 4,5-bis(trifluoromethyl)imidazolidine-2-thione with urea gave mainly trifluoromethyl-containing thioglycoluril. The reaction of perfluorobiacetyl with thiourea produced 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-thione, mainly in trans-form, in a yield of ∼60%. 4,5-Dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-thione(one) were introduced for the first time in the condensation with thiourea in dimethylacetamide at elevated temperature and trifluoromethylated thioxo(oxo)imidazothiazolones were unexpectedly obtained (yield ∼41 − 30%). A similar reaction of 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-thione(one) with NH4SCN and 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-thione with N-alkyl(aryl)ureas and N,N'-dialkyl(diaryl)ureas afforded the same thioxo(oxo)imidazothiazolones (yield ∼50 − 16%). In contrast to it, the condensation of 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-thione with urea under similar conditions gave mainly trifluoromethylated thioglycoluril in ∼31% yield.