基于氮氧烯丙基正离子与不饱和醛、靛红和烯丙基亚胺反应研究

发布时间：2018-02-24 19:35

本文关键词： VA唑烷-4-酮 α-卤代酰胺 [3+2]环加成反应 3-吲哚甲酰胺类衍生物　出处：《西华师范大学》2017年硕士论文　论文类型：学位论文

【摘要】：本文综述了近年来VA唑烷-4-酮的合成方法。VA唑烷-4-酮骨架普遍存在于天然产物和药物分子中,具有很好的生物活性和药用价值,其合成方法引起了化学家们的普遍关注。文献报道了下面几种方法:1)氧吖丙烷与烯酮,吖内酯,胺内酯化合物的环加成反应;2)α-酮酰胺的光催化反应;3)烯醇醚类与N-羟基-α-溴代酰胺的克莱森缩合反应;4)α-羟基酰胺与羰基化合物的缩合反应。本文研究了α-卤代酰胺与α,β-不饱和醛高区域选择性发生环加成反应,高效地得到了VA唑烷-4-酮类衍生物。在碱的作用下,α-卤代酰胺原位产生氮氧烯丙基正离子,氮氧烯丙基正离子与α,β-不饱和醛反应,得到VA唑烷-4-酮类衍生物,收率达到以(90-95%)。在最优条件下,对底物进行了拓展,通过单晶衍射,确定了产物的相对构型。本文还研究了氮氧烯丙基正离子与靛红的[3+2]环加成反应,以高达96%的收率得到螺环结构的VA唑烷-4-酮类化合物。通过筛选碱、温度和溶剂等,获得最优反应条件。在最优条件下,对底物进行了拓展,底物具有较宽的普适性。通过单晶衍射确定了产物的相对构型。除此之外,本文还研究了氮氧烯丙基正离子与α,β-不饱亚胺的反应。以高达93%的收率得到3-吲哚甲酰胺类衍生物。通过筛选碱、温度和溶剂等,获得了最优反应条件。在最优条件下,对底物进行了拓展,底物具有较宽的普适性,以高收率得到了3-吲哚甲酰胺类化合物。通过单晶衍射确定了产物的相对构型。
[Abstract]:In this paper, the synthetic method of VAZO-4-one was reviewed. The skeleton of VAZO-4-one was widely found in natural products and drug molecules, and had good biological activity and medicinal value. The synthesis method has attracted the general attention of chemists. The following methods have been reported in the literature: 1) Oxyacridine propane and ketene, acridine lactone, Cycloaddition reaction of Aminolactone compounds: 2) photocatalytic reaction of 伪 -ketoamides ~ (3) enol ethers with Clayson condensation reaction of N- hydroxy-伪 -bromoamide 4) -Hydroxyamides with Carbonyl compounds. 伪 -haloacyl is studied in this paper. The cycloaddition reaction of amines with 伪, 尾 -unsaturated aldehydes occurs selectively in the high region of 伪, 尾 -unsaturated aldehydes. Under the action of alkaloids, 伪 -haloamides in situ produced azoallyl positive ions, azoallyl anions reacted with 伪, 尾 -unsaturated aldehydes, and VA azolidine-4-one derivatives were obtained by the reaction of alkaloids with 伪, 尾 -unsaturated aldehydes, and the azooxallyl anions reacted with 伪, 尾 -unsaturated aldehydes in the presence of alkaloids. Under the optimum conditions, the substrate was expanded and the relative configuration of the product was determined by single crystal diffraction. The [32] cycloaddition reaction of azoallyl positive ion with indirubin was also studied in this paper. VAZO-4-one compounds with snail structure were obtained in a yield of up to 96%. The optimum reaction conditions were obtained by screening the base, temperature and solvent. Under the optimum conditions, the substrate was expanded. The substrate has wide universality. The relative configuration of the product is determined by single crystal diffraction. In addition, The reaction of azoallyl positive ions with 伪, 尾 -unsaturated imines was also studied. The 3-indoleformamide derivatives were obtained in a yield of up to 93%. The optimum reaction conditions were obtained by screening bases, temperatures and solvents. The substrate was extended and the substrate was widely used. The 3-indoleformamide compounds were obtained in high yield. The relative configuration of the product was determined by single crystal diffraction.
【学位授予单位】：西华师范大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.25

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