当前位置：
X-MOL 学术
›
Chem. Rev.
›
论文详情
Our official English website, www.x-mol.net, welcomes your
feedback! (Note: you will need to create a separate account there.)
Late-Stage C–H Functionalization of Azines
Chemical Reviews ( IF 51.4 ) Pub Date : 2023-05-03 , DOI: 10.1021/acs.chemrev.2c00881 Celena M Josephitis 1 , Hillary M H Nguyen 1 , Andrew McNally 1
Chemical Reviews ( IF 51.4 ) Pub Date : 2023-05-03 , DOI: 10.1021/acs.chemrev.2c00881 Celena M Josephitis 1 , Hillary M H Nguyen 1 , Andrew McNally 1
Affiliation
|
Azines, such as pyridines, quinolines, pyrimidines, and pyridazines, are widespread components of pharmaceuticals. Their occurrence derives from a suite of physiochemical properties that match key criteria in drug design and is tunable by varying their substituents. Developments in synthetic chemistry, therefore, directly impact these efforts, and methods that can install various groups from azine C–H bonds are particularly valuable. Furthermore, there is a growing interest in late-stage functionalization (LSF) reactions that focus on advanced candidate compounds that are often complex structures with multiple heterocycles, functional groups, and reactive sites. Because of factors such as their electron-deficient nature and the effects of the Lewis basic N atom, azine C–H functionalization reactions are often distinct from their arene counterparts, and the application of these reactions in LSF contexts is difficult. However, there have been many significant advances in azine LSF reactions, and this review will describe this progress, much of which has occurred over the past decade. It is possible to categorize these reactions as radical addition processes, metal-catalyzed C–H activation reactions, and transformations occurring via dearomatized intermediates. Substantial variation in reaction design within each category indicates both the rich reactivity of these heterocycles and the creativity of the approaches involved.
中文翻译：
吖嗪的后期C-H功能化
吖嗪，例如吡啶、喹啉、嘧啶和哒嗪，是药物中广泛使用的成分。它们的出现源于一系列符合药物设计关键标准的理化特性，并且可以通过改变其取代基来调节。因此，合成化学的发展直接影响这些努力，并且可以从吖嗪 C-H 键安装各种基团的方法特别有价值。此外，人们对后期功能化（LSF）反应越来越感兴趣，这些反应专注于高级候选化合物，这些化合物通常是具有多个杂环、官能团和反应位点的复杂结构。由于其缺电子性质和路易斯碱性N原子的影响等因素，吖嗪C-H官能化反应通常与其芳烃对应物不同，并且这些反应在LSF背景下的应用很困难。然而，吖嗪 LSF 反应已经取得了许多重大进展，这篇综述将描述这些进展，其中大部分发生在过去十年中。可以将这些反应归类为自由基加成过程、金属催化的 C-H 活化反应以及通过脱芳构中间体发生的转化。每个类别内反应设计的巨大差异表明这些杂环的丰富反应性和所涉及方法的创造性。
更新日期：2023-05-03
中文翻译：
吖嗪的后期C-H功能化
吖嗪，例如吡啶、喹啉、嘧啶和哒嗪，是药物中广泛使用的成分。它们的出现源于一系列符合药物设计关键标准的理化特性，并且可以通过改变其取代基来调节。因此，合成化学的发展直接影响这些努力，并且可以从吖嗪 C-H 键安装各种基团的方法特别有价值。此外，人们对后期功能化（LSF）反应越来越感兴趣，这些反应专注于高级候选化合物，这些化合物通常是具有多个杂环、官能团和反应位点的复杂结构。由于其缺电子性质和路易斯碱性N原子的影响等因素，吖嗪C-H官能化反应通常与其芳烃对应物不同，并且这些反应在LSF背景下的应用很困难。然而，吖嗪 LSF 反应已经取得了许多重大进展，这篇综述将描述这些进展，其中大部分发生在过去十年中。可以将这些反应归类为自由基加成过程、金属催化的 C-H 活化反应以及通过脱芳构中间体发生的转化。每个类别内反应设计的巨大差异表明这些杂环的丰富反应性和所涉及方法的创造性。
京公网安备 11010802027423号