A Decarboxylative C(sp3)-N Bond Forming Reaction to Construct 4-Imidazolidinones via Post-Ugi Cascade Sequence in One Pot
A Decarboxylative C(sp3)-N Bond Forming Reaction to Construct 4-Imidazolidinones via Post-Ugi Cascade Sequence in One Pot
复制标题
脱羧 C(sp(3))-N 键形成反应通过一锅后 Ugi 级联序列构建 4-咪唑啉酮
DOI：
10.1002/adsc.202000736
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发表时间：
2020-07-31
影响因子：
5.4
通讯作者：
Xu, Zhi-Gang
中科院分区：
文献类型：
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作者：
Song, Gui-Ting;Qu, Chuan-Hua;Xu, Zhi-Gang
开发了后 Ugi 一锅级联，通过分子内脱羧 C(sp(3))-N 键形成反应获得 4-咪唑啉酮。该反应对多种取代醛、苯胺、异氰化物和乙醛酸具有广泛的耐受性。将Ugi反应中的醛用脂肪酮取代，扩大级联反应范围，合成螺酰咪唑烷酮。随后，应用该方法在温和、简便的条件下一次纯化合成了药物GSK2137305和SCH 900822的核心结构。这种级联反应为通过可调节的 Ugi 输入定制合成一系列具有生物活性的 4-咪唑啉酮提供了机会。
A post-Ugi one-pot cascade was developed to access 4-imidazolidinones through an intramolecular decarboxylative C(sp(3))-N bond forming reaction. The reaction has a broad tolerance for a variety of substituted aldehydes, anilines, isocyanides and glyoxylic acids. The cascade reaction scope was expanded to synthesize spiroimidazolidi-none by the replacement of aldehyde with aliphatic ketone in the Ugi reaction. Subsequently, the methodology was applied to synthesize the core structures of pharmaceuticals GSK2137305 and SCH 900822 under the mild and facile conditions with one purification. This cascade reaction generates opportunities for the tailored synthesis of a range of biologically active 4-imidazolidinones through tuneable Ugi inputs.