Benzimidazoles represent common chemical moieties in bioactive compounds. The synthesis of this heterocycle often involves a condensation of an ortho-phenylenediamine with a carboxylic acid derivative. The observed dialkylation of the starting ortho-phenylenediamine is avoided by opening of lactones or lactams. This strategy can directly yield 1H-benzimidazoles substituted at the 2-position by a functionalized chain. We present herein a study of the effect of different electron-withdrawing or electron-donating groups at the 4-position of ortho-phenylenediamines on the opening of lactones or lactams to synthesize benzimidazol-2-yl alkanols and benzimidazol-2-yl alkylamines.

中文翻译：

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邻苯二胺的取代基在内酯和内酰胺的开环中对苯并咪唑-2-基烷醇和苯并咪唑-2-基烷胺的影响的研究

苯并咪唑代表生物活性化合物中的常见化学部分。该杂环的合成通常涉及邻苯二胺与羧酸衍生物的缩合。通过打开内酯或内酰胺避免了所观察到的起始邻苯二胺的二烷基化。这种策略可以直接产生在 2 位被功能化链取代的 1H-苯并咪唑。我们在此研究了邻苯二胺 4 位不同吸电子或给电子基团对内酯或内酰胺打开合成苯并咪唑-2-基烷醇和苯并咪唑-2-基烷基胺的影响。