Synthetic studies pertaining to the 2,3-pyridyne and 4,5-pyrimidyne
Synthetic studies pertaining to the 2,3-pyridyne and 4,5-pyrimidyne
复制标题
DOI：
10.1016/j.tet.2016.02.038
复制
发表时间：
2016-06-30
期刊：
影响因子：
2.1
通讯作者：
Garg, Neil K.
中科院分区：
文献类型：
--
作者：
Medina, Jose M.;Jackl, Moritz K.;Garg, Neil K.
本文报道了两种杂环芳炔中间体2，3-吡啶炔和4，5-嘧啶炔的合成研究。首先，使用已知的方法容易地从2-吡啶酮获得2，3-吡啶酮前体。随后，2，3-吡啶生成和捕获用于以区域选择性方式获得几种官能化吡啶。此外，我们报告了两个异构体甲硅烷基三氟甲磺酸酯，这是打算作为前体的4，5-嘧啶炔的合成路线。连续的4，5-嘧啶炔生成和捕获实验最终被认为是没有结果的。我们希望这些发现将促进使用2，3-吡啶和其他杂环芳基作为功能化杂环合成的结构单元。(C)2016爱思唯尔有限公司版权所有
We report synthetic studies pertaining to two heterocyclic aryne intermediates: the 2,3-pyridyne and the 4,5-pyrimidyne. First, a 2,3-pyridyne precursor was readily accessed from 2-pyridone using a known procedure. Subsequently, 2,3-pyridyne generation and trapping were used to access several functionalized pyridines in a regioselective manner. In addition, we report synthetic routes to two isomeric silyltrifiates, which were intended to serve as precursors to the 4,5-pyrimidyne. Consecutive 4,5-pyrimidyne generation and trapping experiments were ultimately deemed unfruitful. We expect these findings will promote the use of 2,3-pyridyne and other heterocyclic arynes as building blocks for the synthesis of functionalized heterocycles. (C) 2016 Elsevier Ltd. All rights reserved.