Department of Chemistry, Georgia State University , Atlanta, Georgia 30303, United States.
Applied Nucleic Acids Research Center & Chemistry Department, Faculty of Sciences, Zagazig University , Zagazig 44519, Egypt.
Org Lett. 2016 Sep 16;18(18):4714-7. doi: 10.1021/acs.orglett.6b02359. Epub 2016 Sep 8.
Trimethylsilyl-transient protection successfully allowed the use of lithium hexamethyldisilazane to prepare benzimidazole (BI) and 4-azabenzimidazole (azaBI) amidines from nitriles in 58-88% yields. This strategy offers a much better choice to prepare BI/azaBI amidines than the lengthy, low-yielding Pinner reaction. Synthesis of aza/benzimidazole rings from aromatic diamines and aldehydes was affected in dimethyl sulfoxide in 10-15 min, while known procedures require long time and purification. These methods are important for the BI/azaBI-based drug industry and for developing specific DNA binders for expanded therapeutic applications.
三甲基硅基瞬时保护成功地允许使用六甲基二硅基锂来制备苯并咪唑(BI)和 4-氮杂苯并咪唑(azaBI)脒,产率为 58-88%。与冗长、低产率的 Pinner 反应相比,该策略为制备 BI/azaBI 脒提供了更好的选择。通过芳香二胺和醛在二甲基亚砜中的反应,可以在 10-15 分钟内合成 aza/苯并咪唑环,而已知的方法需要很长时间和纯化。这些方法对于基于 BI/azaBI 的药物工业以及开发用于扩展治疗应用的特定 DNA 结合物非常重要。