The synthesis of novel imidazole derivatives via immobilized α-acylamino ketones is reported in this article. The key intermediates were prepared from the Wang-piperazine resin-supported Fmoc-amino acids. After their sulfonylation with 4-nitrobenzenesulfonyl chloride (4-Nos-Cl), followed by alkylation with α-bromoketones and cleavage of Nos group, the resulting α-acylamino ketones were reacted with Fmoc-isothiocyanate. The corresponding Fmoc-thioureas were subjected to the Fmoc-cleavage and spontaneous ring-closure to imidazole scaffold. The resulting imidazole-thiones were alkylated with alkyl halides and oxidized using meta-chloroperbenzoic acid (mCPBA). Trifluoroacetic acid (TFA)-mediated cleavage yielded the corresponding trisubstituted 2-alkylsulfonyl imidazoles in good crude purity and acceptable overall yields. In the case of sulfides, prepared from alkyl bromides, the unexpected products brominated at the C⁴ position of the imidazole were obtained.

中文翻译：

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由固定化的α-酰基氨基酮合成具有三个多样性位置的2-烷基磺酰基咪唑

本文报道了通过固定化的α-酰基氨基酮合成新型咪唑衍生物的方法。关键中间体是从Wang-哌嗪树脂负载的Fmoc-氨基酸制备的。用4-硝基苯磺酰氯（4-Nos-Cl）进行磺酰化后，用α-溴代烷基烷基化并裂解Nos基团，使所得的α-酰基氨基酮与Fmoc-异硫氰酸酯反应。对相应的Fmoc-硫脲进行Fmoc切割，并自发闭合咪唑支架。将所得的咪唑-硫酮用烷基卤化物烷基化，并使用间氯过苯甲酸（mCPBA）。三氟乙酸（TFA）介导的裂解以良好的粗纯度和可接受的总产率得到了相应的三取代的2-烷基磺酰基咪唑。在由烷基溴制备的硫化物的情况下，获得了在咪唑的C ⁴位溴化的意外产物。