Parallel Synthesis of 2-Sulphanylated Bis-benzimidazoles on Soluble Polymer Support

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• 作者：Chia-Mao Chang ; Manohar V. Kulkarni ; Chih-Hau Chen ; Chi-Hsiang Wang ; Chung-Ming Sun
• 刊名：Journal of Combinatorial Chemistry
• 出版年：2008
• 出版时间：May 2008
• 年：2008
• 卷：10
• 期：3
• 页码：466 - 474
• 全文大小：175K
• 年卷期：v.10,no.3(May 2008)
• ISSN：1520-4774

文摘

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.