Abstract

Although ninhydrin is an essential analytical tool in biochemical and forensic sciences, for the past several years, it has been employed as efficient building block for diverse organic scaffolds. In the present work, the ortho selectivity of ninhydrin-phenol adducts has been exploited to obtain 2-(2′-hydroxyaryl)benzimidazoles which are well known excited state intramolecular proton transfer (ESIPT) fluorophores. Under acidic condition, 3-(2-hydroxyaroyl)isoindolin-1-one intermediate generated in situ from ninhydrin-phenol adducts was treated with o-phenylenediamine resulting benzimidazole scaffolds via a two-step one pot strategy.

摘要

尽管茚三酮是生化和法医学中必不可少的分析工具，但在过去几年中，它已被用作各种有机支架的有效构建块。在目前的工作中，茚三酮-苯酚加合物的邻位选择性已被用于获得 2-(2'-羟基芳基)苯并咪唑，这是众所周知的激发态分子内质子转移 (ESIPT) 荧光团。在酸性条件下，由茚三酮-苯酚加合物原位生成的 3-(2-羟基芳酰基)isoindolin-1-one 中间体通过两步一锅策略用邻苯二胺生成的苯并咪唑支架处理。