一种简单的 Cu 催化取代 3-吡啶醇和 5-嘧啶醇抗氧化剂的偶联方法。

A simple Cu-catalyzed coupling approach to substituted 3-pyridinol and 5-pyrimidinol antioxidants.

机构信息

Department of Chemistry, Queen's University, Kingston, ON, Canada K7L 3N6.

出版信息

J Org Chem. 2008 Dec 5;73(23):9326-33. doi: 10.1021/jo801501e.

Abstract

A convenient approach to 3-pyridinols and 5-pyrimidinols via a two-step Cu-catalyzed benzyloxylation/catalytic hydrogenation sequence is presented. The corresponding 3-pyridinamines and 5-pyrimidinamines can be prepared in an analogous sequence utilizing benzylamine in lieu of benzyl alcohol. The radical-scavenging ability of these derivatives are preliminarily explored and reveal that the increased acidities of the pyridinols and pyrimidinols render them susceptible to more significant kinetic solvent effects when compared to phenols.

摘要

本文提出了一种通过两步 Cu 催化苄氧基化/催化氢化序列来制备 3-吡啶醇和 5-嘧啶醇的简便方法。利用苄胺代替苄醇，也可以采用类似的序列来制备相应的 3-吡啶胺和 5-嘧啶胺。初步探索了这些衍生物的清除自由基能力，结果表明，与苯酚相比，吡啶醇和嘧啶醇的酸性增加，使它们更容易受到更显著的动力学溶剂效应的影响。