本文關(guān)鍵詞： VA唑烷-4-酮 α-鹵代酰胺 [3+2]環(huán)加成反應(yīng) 3-吲哚甲酰胺類衍生物　出處：《西華師范大學(xué)》2017年碩士論文　論文類型：學(xué)位論文

【摘要】：本文綜述了近年來VA唑烷-4-酮的合成方法。VA唑烷-4-酮骨架普遍存在于天然產(chǎn)物和藥物分子中,具有很好的生物活性和藥用價值,其合成方法引起了化學(xué)家們的普遍關(guān)注。文獻報道了下面幾種方法:1)氧吖丙烷與烯酮,吖內(nèi)酯,胺內(nèi)酯化合物的環(huán)加成反應(yīng);2)α-酮酰胺的光催化反應(yīng);3)烯醇醚類與N-羥基-α-溴代酰胺的克萊森縮合反應(yīng);4)α-羥基酰胺與羰基化合物的縮合反應(yīng)。本文研究了α-鹵代酰胺與α,β-不飽和醛高區(qū)域選擇性發(fā)生環(huán)加成反應(yīng),高效地得到了VA唑烷-4-酮類衍生物。在堿的作用下,α-鹵代酰胺原位產(chǎn)生氮氧烯丙基正離子,氮氧烯丙基正離子與α,β-不飽和醛反應(yīng),得到VA唑烷-4-酮類衍生物,收率達(dá)到以(90-95%)。在最優(yōu)條件下,對底物進行了拓展,通過單晶衍射,確定了產(chǎn)物的相對構(gòu)型。本文還研究了氮氧烯丙基正離子與靛紅的[3+2]環(huán)加成反應(yīng),以高達(dá)96%的收率得到螺環(huán)結(jié)構(gòu)的VA唑烷-4-酮類化合物。通過篩選堿、溫度和溶劑等,獲得最優(yōu)反應(yīng)條件。在最優(yōu)條件下,對底物進行了拓展,底物具有較寬的普適性。通過單晶衍射確定了產(chǎn)物的相對構(gòu)型。除此之外,本文還研究了氮氧烯丙基正離子與α,β-不飽亞胺的反應(yīng)。以高達(dá)93%的收率得到3-吲哚甲酰胺類衍生物。通過篩選堿、溫度和溶劑等,獲得了最優(yōu)反應(yīng)條件。在最優(yōu)條件下,對底物進行了拓展,底物具有較寬的普適性,以高收率得到了3-吲哚甲酰胺類化合物。通過單晶衍射確定了產(chǎn)物的相對構(gòu)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 偽 -ketoamides ~ (3) enol ethers with Clayson condensation reaction of N- hydroxy-偽 -bromoamide 4) -Hydroxyamides with Carbonyl compounds. 偽 -haloacyl is studied in this paper. The cycloaddition reaction of amines with 偽, 尾 -unsaturated aldehydes occurs selectively in the high region of 偽, 尾 -unsaturated aldehydes. Under the action of alkaloids, 偽 -haloamides in situ produced azoallyl positive ions, azoallyl anions reacted with 偽, 尾 -unsaturated aldehydes, and VA azolidine-4-one derivatives were obtained by the reaction of alkaloids with 偽, 尾 -unsaturated aldehydes, and the azooxallyl anions reacted with 偽, 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 偽, 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.
【學(xué)位授予單位】：西華師范大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2017
【分類號】：O621.25

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