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电化学和机械化学策略作为合成具有生物学相关性的3-硝基咪唑并[1,2 -]吡啶的双重合成方法

Electro- and Mechanochemical Strategy as a Dual Synthetic Approach for Biologically Relevant 3-Nitro-imidazo-[1,2-]pyridines.

作者信息

Mukherjee Debojyoti, Karmakar Indrajit, Brahmachari Goutam

机构信息

Laboratory of Natural Products & Organic Synthesis, Department of Chemistry, Visva-Bharati (a Central University), Santiniketan, West Bengal 731 235, India.

出版信息

J Org Chem. 2024 Sep 6;89(17):12071-12084. doi: 10.1021/acs.joc.4c00881. Epub 2024 Aug 15.

Abstract

We herein disclose a dual synthetic approach involving electrochemical and mechanochemical strategies for diversely functionalized 3-nitro-2-aryl-immidazo[1,2-]pyridines. Both methods offer a practical and straightforward alternative route for accessing this important class of biologically promising nitrogen-containing heterocycles. Significant advantages of the newly developed methods include mild and energy-efficient reaction conditions, avoidance of transition metal catalysts, external heating and additional oxidants, shorter reaction times, good to excellent yields, broad substrate scope, gram-scale applicability, operational simplicity, and eco-friendliness. Furthermore, a synthetic application was extended by successfully reducing synthesized 3-nitro-2-aryl-immidazo[1,2-]pyridines to their corresponding amino derivatives.

摘要

我们在此公开了一种涉及电化学和机械化学策略的双重合成方法,用于制备功能多样的3-硝基-2-芳基咪唑并[1,2 - ]吡啶。这两种方法都为获取这类具有重要生物学前景的含氮杂环化合物提供了实用且直接的替代途径。新开发方法的显著优点包括温和且节能的反应条件、无需过渡金属催化剂、外部加热和额外氧化剂、反应时间短、产率良好至优异、底物范围广、克级规模适用性、操作简便以及环境友好性。此外,通过成功地将合成的3-硝基-2-芳基咪唑并[1,2 - ]吡啶还原为相应的氨基衍生物,扩展了其合成应用。

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