Under both conventional method (CM) and microwave (MW) irradiation (MWI) conditions, alkylation of 4,5-diphenylimidazole-2-thione (1) with halogeno-alkanols 2 or 5, chloroglycerol 11 and 2,3-O-isopropylidene-1-O-(p-tolylsulfonyl)-glycerol (8) in presence of sodium ethoxide or sodium acetate in alcohol afforded regioselectively the corresponding S-alkylated analogues 3, 6, 9, and 12; they also were obtained using MW in absence and presence of bentonite as solid support with no change in regioselectivity. In the presence of potassium carbonate in DMF, the bisalkylated analogues 4, 7, 10, and 13 were obtained except in case of compound 13 where it was accompanied with the imidazothiazine 14. A convenient approach for imidazo-[2,1-b]thiazines and thiazoles 14-16 could be achieved by intramolecular dehydrative ring closure of the S-hydroxyalkylated imidazoles 3, 6, and 12 using potassium carbonate in DMF under both conventional and microwave methods. Isopropylidenation of 12 and 13 and deprotection of 9 and 10 also were investigated.

译文

:在常规方法(CM)和微波(MW)照射条件下,均用卤代链烷醇2或5,氯甘油11和2,3-O-将4,5-二苯基咪唑-2-硫酮(1)烷基化在乙醇钠或乙酸钠存在下,在异丙醇中的异亚丙基-1-O-(对甲苯磺酰基)-甘油(8)选择性地提供相应的S-烷基化的类似物3、6、9和12;它们也可以在不存在和存在膨润土作为固体载体的情况下使用MW获得,其区域选择性没有变化。在DMF中存在碳酸钾的情况下,获得双烷基化的类似物4、7、10和13,除了化合物13与咪唑并噻嗪14结合的情况外。咪唑-[2,1-b]的简便方法噻嗪和噻唑14-16可以通过在传统方法和微波方法下使用碳酸钾在DMF中对S-羟烷基化的咪唑3、6和12进行分子内脱水闭环来实现。还研究了12和13的异亚丙基化和9和10的脱保护。

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