Unlike secondary alkyl amines and electron-rich anilines, secondary electron-poor anilines are challenging amine sources to explore the chemical space of Lewis acid-catalyzed condensation-based transformations with furfural. In this work, we report the efficient synthesis of trans-4,5-diamino cyclopentenones (DCP) using a high-pressure promoted Nazarov-like electrocyclization of Stenhouse salts arising from the Sc(III)-catalyzed condensation of furfural with secondary electron-poor anilines. The reaction enables access to otherwise difficult-to-access DCP and compatibility with a large scope of alkyl and aryl secondary amines. A 2- to 18-fold increase in yields for electron-poor anilines was highlighted using this approach in the synthesis of a pharmacologically active compound.

中文翻译：

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高压促进的纳扎罗夫式电环化能够获得带有贫电子苯胺的反式4,5-二氨基-环戊-2-烯酮

与仲烷基胺和富电子苯胺不同，仲贫电子苯胺是探索路易斯酸催化与糠醛缩合反应的化学空间的具有挑战性的胺源。在这项工作中，我们报道了利用 Sc(III) 催化糠醛与二次电子缩合产生的 Stenhouse 盐的高压促进类纳扎罗夫电环化，有效合成了反式-4,5-二氨基环戊烯酮 (DCP)。可怜的苯胺。该反应能够获得原本难以获得的 DCP，并与多种烷基和芳基仲胺相容。使用这种方法合成药理活性化合物时，缺电子苯胺的产率可提高 2 至 18 倍。