基于叶立德的串联反应高效构筑吲哚衍生物的研究
发布时间：2019-05-21 16:18
【摘要】：吲哚和氧化吲哚衍生物具有良好的生物活性和潜在的药用价值。因此,开发新型高效方法合成吲哚衍生物已经受到相当大的关注。在本文中,使用吲哚衍生物作为底物通过与具有多个反应位点的活泼叶立德相结合合成取代的吲哚衍生物。共完成了四个Domino反应,涉及膦叶立德,硫叶立德和甲亚胺叶立德,为合成一些杂环化合物提供新的思路和方法。1)首先研究了无催化剂Domino反应用于合成3-(环戊烯酮)氧化吲哚衍生物,该方法是膦叶立德引发的Wittig-Michael addition-Wittig Domino反应模式的第一个实例。温和的反应条件和良好的底物适应性使其对于合成3-(环戊烯酮)氧化吲哚衍生物有非常高的实用价值。2)其次,我们又研究了碳酸铯促进的砜基吲哚与巴豆酸衍生的硫叶立德之间的[2,3]-σ重排反应,该反应为合成含有烯丙基硫醚基团的3-取代吲哚衍生物提供了简单、高效的反应模式,在该Domino反应中,一个C-C旧键断裂,两个C-C新键生成。3)另外,我们又研究了没有任何金属或外部氧化剂的情况下哌啶N-H/α,α,β,β-C(sp~3)-H的直接官能化。该反应在4-(三氟甲基)苯甲酸的作用下,经由甲亚胺叶立德中间体,这是一种用于合成具有3-取代的氧化吲哚螺环吲哚的简单方法。4)最后在上述工作的基础上,继续研究了芳酸促进的氮杂环庚烷的α-C-H官能化,得到含有七元环结构的螺环氧化吲哚衍生物,该反应在4-氟苯甲酸的作用下,经由甲亚胺叶立德中间体,这是一种高效合成含有氮杂环庚烷部分的螺环氧化吲哚衍生物的方法。
[Abstract]:Indole and indole oxide derivatives have good biological activity and potential medicinal value. Therefore, the development of new and efficient methods for the synthesis of indole derivatives has attracted considerable attention. In this paper, indole derivatives were used as substrate to synthesize substituted indole derivatives by combining with active Yeride with multiple reaction sites. A total of four Domino reactions were completed, involving phosphine Yeride, thioylide and methimine Yeride. It provides a new idea and method for the synthesis of some heterocycle compounds. 1) the uncatalyzed Domino reaction for the synthesis of 3-(cyclopentenone) oxidative indole derivatives was studied. This method is the first example of Wittig-Michael addition-Wittig Domino reaction model initiated by phosphine Yeride. Mild reaction conditions and good substrate adaptability make it have very high practical value for the synthesis of 3-(cyclopentenone) oxidized indole derivatives. 2) secondly, We have also studied the [2, 3]-蟽 rearrangement reaction between sulfoindole promoted by cesium carbonate and thiolide derived from Croton acid, which provides a simple reaction for the synthesis of 3-substituted indole derivatives containing allyl thioether groups. In the Domino reaction, one C 鈮，
本文编号：2482223
[Abstract]:Indole and indole oxide derivatives have good biological activity and potential medicinal value. Therefore, the development of new and efficient methods for the synthesis of indole derivatives has attracted considerable attention. In this paper, indole derivatives were used as substrate to synthesize substituted indole derivatives by combining with active Yeride with multiple reaction sites. A total of four Domino reactions were completed, involving phosphine Yeride, thioylide and methimine Yeride. It provides a new idea and method for the synthesis of some heterocycle compounds. 1) the uncatalyzed Domino reaction for the synthesis of 3-(cyclopentenone) oxidative indole derivatives was studied. This method is the first example of Wittig-Michael addition-Wittig Domino reaction model initiated by phosphine Yeride. Mild reaction conditions and good substrate adaptability make it have very high practical value for the synthesis of 3-(cyclopentenone) oxidized indole derivatives. 2) secondly, We have also studied the [2, 3]-蟽 rearrangement reaction between sulfoindole promoted by cesium carbonate and thiolide derived from Croton acid, which provides a simple reaction for the synthesis of 3-substituted indole derivatives containing allyl thioether groups. In the Domino reaction, one C 鈮，
本文编号：2482223
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