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Synthesis of trifluoromethyl – containing oxo(thioxo)imidazothiazolones and thioglycolurils based on perfluorobiacetyl
Journal of Fluorine Chemistry ( IF 1.7 ) Pub Date : 2018-06-01 , DOI: 10.1016/j.jfluchem.2018.05.015
L.V. Saloutina , A.Ya. Zapevalov , M.I. Kodess , I.N. Ganebnykh , V.I. Saloutin , O.N. Chupakhin

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.



中文翻译:

基于全氟双乙酰基的含三氟甲基的含氧代(thioxo)咪唑并噻唑酮和硫代糖尿嘧啶的合成

全氟联乙酰与硫脲的反应生成了4,5-二羟基-4,5-双(三氟甲基)咪唑烷-2-硫酮,主要为反式形式,收率为〜60%。首次在高温下与二甲基乙酰胺中的硫脲缩合反应中首次引入4,5-二羟基-4,5-双(三氟甲基)咪唑烷-2-硫酮(一),意外地获得了三氟甲基化的硫代(氧代)咪唑并噻唑酮(收率) 〜41-30%)。4,5-二羟基-4,5-双(三氟甲基)咪唑烷-2-硫酮(一个)与NH 4 SCN和4,5-二羟基-4,5-双(三氟甲基)咪唑烷-2-硫酮的相似反应具有N-烷基(芳基)脲和N,N'-二烷基(二芳基)脲提供了相同的硫代(氧代)咪唑并噻唑酮(收率约50-16%)。与此相反,在相似的条件下,4,5-二羟基-4,5-双(三氟甲基)咪唑烷-2-硫酮与尿素的缩合反应主要得到三氟甲基化的巯基脲,收率为31%。

更新日期:2018-06-01
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