A 2-amido benzo[d]imidazole library has been constructed by solid-phase synthesis. The key step of this solid-phase synthesis involves the preparation of polymer-bound 2-amino benzo[d]imidazole resin through desulfurative cyclization of thiourea resin using 2-chloro-1,3-dimethylimidazolinium chloride and N,N-diisopropylethylamine in dichloromethane (DCM), and the resin is then functionalized by acylation at the 2-amine position to afford 2-amidobenzo[d]imidazole resin. In the case of 2-amidobenzo[d]imidazole resin having a p-I or m-NO₂, the resin was further functionalized by Suzuki/Sonogashira-coupling (p-I) and reduction to the primary amine (m-NO₂) followed by acylation. Finally, the functionalized 2-amido-benzo[d]imidazole resin was cleaved from the polymer support by treatment with a cocktail of trifluoroacetic acid and DCM. As a result, we obtained 2-amidobenzo[d]imidazole analogues in high yield and good purities.

中文翻译：

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固相硫脲中间树脂的脱硫环化反应制备2-氨基酰胺基苯并[ d ]咪唑类似物

通过固相合成已经构建了2-氨基苯并[ d ]咪唑文库。该固相合成的关键步骤涉及使用2-氯-1,3-二甲基咪唑啉鎓氯化物和N，N-二异丙基乙胺的二氯甲烷溶液，通过硫脲树脂的脱硫环化反应，制备与聚合物结合的2-氨基苯并[ d ]咪唑树脂。 （DCM），然后通过2-胺位置的酰化作用将树脂官能化，得到2-酰胺基苯并[ d ]咪唑树脂。在具有p -I或m -NO ₂的2-酰胺基苯并[ d ]咪唑树脂的情况下，该树脂通过Suzuki / Sonogashira偶联进一步官能化（p -I）还原为伯胺（m -NO ₂），然后进行酰化反应。最后，通过用三氟乙酸和DCM的混合物处理，将官能化的2-酰胺基-苯并[ d ]咪唑树脂从聚合物载体上裂解下来。结果，我们以高收率和良好的纯度获得了2-酰胺基苯并[ d ]咪唑类似物。