Access to Pyrazolidin-3,5-diones through Anodic N-N Bond Formation
Access to Pyrazolidin-3,5-diones through Anodic N-N Bond Formation
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DOI：
10.1002/anie.201603899
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发表时间：
2016-08-01
影响因子：
16.6
通讯作者：
Waldvogel, Siegfried R.
中科院分区：
文献类型：
--
作者：
Gieshoff, Tile;Schollmeyer, Dieter;Waldvogel, Siegfried R.
吡唑烷-3，5-二酮是杂环化学中的重要基元，在医药领域具有重要的应用价值。在经典的有机合成中，肼部分是通过使用相应的肼构建块通过缩合来安装的。然而，大多数N，N‘-二芳基肼是有毒的，需要上游制备，因为它们的商业可用性较低。我们提出了一种替代的和可持续的合成吡唑烷-3，5-二酮的方法，该方法使用容易获得的二苯胺作为前体，这些二苯胺被阳极转化为N-N键。电转换是在恒流条件下在简单的不分割电池中进行的。
Pyrazolidin-3,5-diones are important motifs in heterocyclic chemistry and are of high interest for pharmaceutical applications. In classic organic synthesis, the hydrazinic moiety is installed through condensation using the corresponding hydrazine building blocks. However, most N,N'-diaryl hydrazines are toxic and require upstream preparation owing to their low commercial availability. We present an alternative and sustainable synthetic approach to pyrazolidin-3,5-diones that employs readily accessible dianilides as precursors, which are anodically converted to furnish the N-N bond. The electroconversion is conducted in a simple undivided cell under constant-current conditions.