The Forgotten Pyrazines: Exploring the Dakin-West Reaction.,Chemistry - A European Journal

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The Forgotten Pyrazines: Exploring the Dakin-West Reaction.
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2020-03-26 , DOI: 10.1002/chem.202000475
Martien A Würdemann ₁ , Cristina Niţu ₂ , Stefaan M A De Wildeman ₁ , Katrien V Bernaerts ₁ , Romano V A Orru ₁

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Pyrazines are an underreported class of N‐heterocycles available from nitrogen‐rich biomass presenting an interesting functional alternative for current aromatics. In this work, access to pyrazines obtained from amino acids by using the 90 year old Dakin–West reaction was explored. After a qualitative screening several functional proteinogenic amino acids proved good substrates for this reaction, which were successfully scaled to multigram scale synthesis of the corresponding intermediate α‐acetamido ketones. Subsequently, the conditions towards pyrazine formation using δ‐amino‐levulinic acid were optimized, and these were employed to synthesize a relevant set of five functional dimethylpyrazines in high purity. These pyrazines can be considered a versatile toolbox of aromatic building blocks for a wide range of applications, such as in the synthesis of polymers or metal–organic frameworks.

中文翻译：

被遗忘的吡嗪类：探索达金-韦斯特反应。

吡嗪类化合物是一种报道较少的N杂环类化合物，可从富氮生物质中获得，为当前的芳族化合物提供了有趣的功能替代品。在这项工作中，探索了使用90年的Dakin-West反应从氨基酸获得的吡嗪的途径。经过定性筛选后，几种功能性蛋白原氨基酸被证明是该反应的良好底物，已成功地按比例缩放至相应的中间体α-乙酰氨基酮的克数合成。随后，优化了使用δ-氨基乙酰丙酸形成吡嗪的条件，并利用这些条件合成了一组相关的五种高纯度的功能性二甲基吡嗪。这些吡嗪被认为是适用于广泛应用的芳香族结构单元的多功能工具箱，

更新日期：2020-03-26

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