Chang Chia-Mao, Kulkarni Manohar V, Chen Chih-Hau, Wang Chi-Hsiang, Sun Chung-Ming
Department of Applied Chemistry, National Chiao Tung University, Hsinchu 300-10, Taiwan, ROC.
J Comb Chem. 2008 May-Jun;10(3):466-74. doi: 10.1021/cc7002045. Epub 2008 Apr 12.
A well-sustained multistep synthetic protocol has been designed for the PEG-functionalized aromatic acid amide to generate a molecular library of 2-alkylthio bis-benzimidazoles. An attempted synthesis of benzimidazole-2-thiol in dichloromethane has led to S-chloromethyl methyl sulfides, mimicking bacterial enzymatic systems. Regioselective S-alkylation was brought about under controlled conditions using a mild base at room temperature. The polymer-free compounds, 2-sulfanylated bisbenzimidazoles, were obtained in high yields and high purities. Chemical shift changes in proton and carbon NMR have been employed to monitor the progress of the reaction steps and to prove the site of S-alkylation, respectively.
已设计出一种用于聚乙二醇功能化芳香酰胺的多步合成方案，以生成2-烷硫基双苯并咪唑的分子库。在二氯甲烷中尝试合成苯并咪唑-2-硫醇时，生成了S-氯甲基甲基硫醚，这类似于细菌酶系统。在室温下使用温和碱在受控条件下实现区域选择性S-烷基化。以高收率和高纯度获得了无聚合物的化合物2-硫代双苯并咪唑。质子核磁共振和碳核磁共振中的化学位移变化已分别用于监测反应步骤的进程和证明S-烷基化的位点。
