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研究生: 洪梓瑀
Hong, Zih-Yu
論文名稱: 2-碘苯胺衍生物和丙炔基二酮類/1-苯基-2-甲苯磺乙酮化合物經由銅催化分子內雙環化氧化級聯反應獲得3-羥基-3-呋喃基異茚二酮衍生物
Copper Catalyzed Oxidative Cascade Inter-Molecular Double Cyclisation of 2-Iodobenzamide Derivatives and Propagyl dicarbonyl/ 1-Phenyl-2-Tosylethanone Compounds for Accessing 3-Hydroxy-3-Furylisoindilinone Derivatives
指導教授: 姚清發
Yao, Ching-Fa
口試委員: 林文偉 姚清發 柳如宗
口試日期: 2021/07/25
學位類別: 碩士
Master
系所名稱: 化學系
Department of Chemistry
論文出版年: 2021
畢業學年度: 109
語文別: 中文
論文頁數: 103
中文關鍵詞: 3-羥基異吲哚啉酮銅催化
英文關鍵詞: copper catalyzed
DOI URL: http://doi.org/10.6345/NTNU202101288
論文種類: 學術論文
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  • 論文描述了3-羥基-3-呋喃基異吲哚啉酮衍生物的合成。本論文的內容分為兩章。第一章介紹了關於3-羥基異吲哚啉酮衍生物的藥用重要性和材料重要性的文獻綜述,以及構建3-羥基異吲哚啉酮衍生物的合成方法。
    第二部分說明了通過銅催化串聯雙環化從炔丙基二羰基化合物和2-碘苯甲酰胺衍生物生成3-羥基-3-呋喃基異吲哚啉酮衍生物的一鍋兩步法。此外,該方法通過探索2-炔基-2-苯磺醯基苯丙酮取代炔基二酮化合物得到3-羥基-2-苯基-3-(5-苯基-4-甲磺醯基)異吲哚啉酮衍生品。該方法相對較快、簡單、方便,可得到範圍廣泛的3-羥基-3-呋喃基異茚二酮衍生物。

    The thesis describes about the synthesis of 3-hydroxy-3-furylisoindolinone derivatives. The contents of this thesis are divided into two chapter. The first chapter describes about the literature review on about medicinal importance and material importance of 3-hydroxyisoindolinone derivatives also synthetic procedures for construction of 3-hydroxyisoindolinone derivatives. Further, the present chapter concludes with the aim of the thesis.
    The second part illustrates one-pot two-step method for the generation of 3-hydroxy-3-furylisoindolinone derivatives from propargyldicarbonyl compounds and 2-Iodobenzamide derivatives via copper catalyzed tandem double cyclization. Further, the methodology was extended by exploring the 2-proparyl-2-phenylsulfonyl-acetophenone by replacing propargyldicarbonyl compounds to obtain 3-hydroxy-2-phenyl-3-(5-phenyl-4-tosylfuran-2-yl)isoindolin-1-one derivatives. This method is relatively faster, simple and convenient to obtain a wide range of 3-hydroxy-3-furyl isoindenedione derivatives.

    目錄 中文摘要 I 英文摘要 II 1. 前言 1 1.1、呋喃(Furan)衍生物介紹 1 1.2、3-羥基異吲哚啉酮介紹 2 1.3、碸衍生物介紹 3 2、文獻回顧 4 2-1、呋喃衍生物合成 4 2-2、3-羥基異吲哚啉酮的合成 6 3.研究目標 8 4、實驗結果與討論 9 4-1、合成不同取代基的化合物 10 4-2、反應機構的探討 20 5、結論 26 6、實驗方法 27 6-1、分析儀器與基本實驗操作 27 6-2、實驗步驟 29 文獻回顧 33 光譜資料 36 光譜附圖 48

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