Journal of Fluorine Chemistry ( IF 1.7 ) Pub Date : 2019-02-07 , DOI: 10.1016/j.jfluchem.2019.02.003 Emilia Obijalska , Magdalena Błaszczyk , Marcin K. Kowalski , Grzegorz Mlostoń , Heinz Heimgartner
A Lewis acid catalyzed reaction of trifluoroacetyldiazomethane (CF3COCHN2) with thiourea occurs in boiling THF solution in the presence of BF3·OEt2 yielding 2-amino-4-trifluoromethyl-1,3-thiazole in a fair yield. Analogous reactions with aromatic thioamides, performed in the presence of a mesylchloride/triethylamine mixture as a dehydrating agent led to the corresponding 2-aryl-4-trifluoromethyl-1,3-thiazoles. Aromatic thioamides also react with CF3COCHN2 under MW irradiation, and after 2 min, the corresponding 1,3-thiazoles were obtained in fair yields. The obtained fluorinated 2-amino-1,3-thiazole was used for the reactions with selected N-alkylating and N-acylating reagents to give trifluoromethylated analogues of commonly known pharmaceuticals with 1,3-thiazole structures (Fanetizole and Lotifazole).
中文翻译:
通过中间体硫代羰基叶立德获得4-三氟甲基-1,3-噻唑衍生物的新途径
Lewis酸催化的三氟乙酰基重氮甲烷(CF 3 COCHN 2)与硫脲的反应在沸腾的THF溶液中,在BF 3 ·OEt 2的存在下以合理的收率产生了2-氨基-4-三氟甲基-1,3-噻唑。在甲磺酰氯/三乙胺混合物作为脱水剂存在下进行的与芳族硫酰胺的类似反应产生相应的2-芳基-4-三氟甲基-1,3-噻唑。芳族硫酰胺在MW辐射下也与CF 3 COCHN 2反应,并且在2分钟后,以合理的收率获得了相应的1,3-噻唑。将所获得的氟化2-氨基-1,3-噻唑用于与选择的N-烷基化和N-酰化试剂,可得到具有1,3-噻唑结构(法尼唑和洛替唑)的常见药物的三氟甲基化类似物。