基于葉立德的串聯反應高效構筑吲哚衍生物的研究
發(fā)布時間：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潛在的藥用價值。因此,開發(fā)新型高效方法合成吲哚衍生物已經受到相當大的關注。在本文中,使用吲哚衍生物作為底物通過與具有多個反應位點的活潑葉立德相結合合成取代的吲哚衍生物。共完成了四個Domino反應,涉及膦葉立德,硫葉立德和甲亞胺葉立德,為合成一些雜環(huán)化合物提供新的思路和方法。1)首先研究了無催化劑Domino反應用于合成3-(環(huán)戊烯酮)氧化吲哚衍生物,該方法是膦葉立德引發(fā)的Wittig-Michael addition-Wittig Domino反應模式的第一個實例。溫和的反應條件和良好的底物適應性使其對于合成3-(環(huán)戊烯酮)氧化吲哚衍生物有非常高的實用價值。2)其次,我們又研究了碳酸銫促進的砜基吲哚與巴豆酸衍生的硫葉立德之間的[2,3]-σ重排反應,該反應為合成含有烯丙基硫醚基團的3-取代吲哚衍生物提供了簡單、高效的反應模式,在該Domino反應中,一個C-C舊鍵斷裂,兩個C-C新鍵生成。3)另外,我們又研究了沒有任何金屬或外部氧化劑的情況下哌啶N-H/α,α,β,β-C(sp~3)-H的直接官能化。該反應在4-(三氟甲基)苯甲酸的作用下,經由甲亞胺葉立德中間體,這是一種用于合成具有3-取代的氧化吲哚螺環(huán)吲哚的簡單方法。4)最后在上述工作的基礎上,繼續(xù)研究了芳酸促進的氮雜環(huán)庚烷的α-C-H官能化,得到含有七元環(huán)結構的螺環(huán)氧化吲哚衍生物,該反應在4-氟苯甲酸的作用下,經由甲亞胺葉立德中間體,這是一種高效合成含有氮雜環(huán)庚烷部分的螺環(huán)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，
本文編號：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，
本文編號：2482223
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