利用 lawsone† 通过机械化学激活的 Biginelli 反应生成前所未有的线性产物

Christina L. Koumpoura, Laure Vendier, Christian Bijani, Anne Robert, Philippe Carbonnière, Jean-Marc Sotiropoulos and Michel Baltas
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引用次数: 0

摘要

研究了涉及 2-羟基-1,4-萘醌(lawsone)、对取代苯甲醛和脲的 Biginelli 反应,这是一种关键的多组分反应。令人惊讶的是,在各种实验条件下都没有观察到经典的 Biginelli 环化 DHPM。与传统液相条件不同的机械化学条件导致了一系列前所未有的 "Biginelli-线性 "律酮衍生物的高产率形成。观察到的结果与 DFT 理论预测一致,突出了在液相条件下迈克尔加合物的优先性以及经典 DHPM 化合物在能量上难以置信的环化途径。此外,该研究还首次实现了 "Biginelli-线性 "律酮衍生物环化成环氨基甲酸酯的新方法。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Unprecedented linear products by a mechanochemically activated Biginelli reaction using lawsone†

Unprecedented linear products by a mechanochemically activated Biginelli reaction using lawsone†

The Biginelli reaction, a crucial multicomponent reaction, was investigated involving 2-hydroxy-1,4-naphthoquinone (lawsone), p-substituted benzaldehydes, and ureas. Surprisingly, the classic Biginelli cyclized DHPM was not observed under various experimental conditions. Mechanochemical conditions, unlike traditional liquid phase conditions, led to the unprecedented formation of a series of ‘Biginelli-linear’ lawsone derivatives with high yields. The observed outcomes were consistent with DFT theoretical predictions, highlighting the preference for the Michael adduct under liquid conditions and the energetically implausible cyclization pathway for the classic DHPM compound. Additionally, the study achieved the novel cyclization of a ‘Biginelli-linear’ lawsone derivative into a cyclic carbamate for the first time.

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