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研究生: 林豊鈞
Lin, Li-Chun
論文名稱: 一、2-碘苯甲醯胺衍生物和炔丙基二羰基化合物以銅金屬催化進行氧化級聯雙環化反應合成3-羥基-3-呋喃基異吲哚酮衍生物 二、以一鍋化方法進行克腦文蓋爾縮合反應/亞胺化/π-Aza 電環化合成三取代吡啶 三、以銅金屬進行串連環化異吲哚並 [1,2-b] 喹唑啉-12(10H)-酮和 5,13-二氫11H-喹唑啉 [2,3-b]喹唑啉-11-酮衍生物
1.Copper Catalyzed Oxidative Cascade Double Cyclization of 2--Iodobenzamide Derivatives and Propargyl dicarbonyl Compounds for Accessing 3-Hydroxy-3-furylisoindoli¬none derivatives 2.One-Pot Three-Component Knoevenagel/Imination/6π-Azaelectrocyclization Sequence for the Synthesis of Trisubstituted Pyridines 3.Synthesis of Isoindolo [1,2-b]quinazolin-12(10H)-one and 5,13-dihydro-11H quinazolino[2,3-b]quinazolin-11-one Derivatives via Copper Catalyzed Tandem Cyclization
指導教授: 姚清發
Yao, Ching-Fa
口試委員: 葉怡均
Yeh, Yi-Chun
林文偉
Lin, Wen-Wei
劉維民
Liu, Wei-Min
柳如宗
Liu, Ju-Tsung
姚清發
Yao, Ching-Fa
口試日期: 2023/07/20
學位類別: 博士
Doctor
系所名稱: 化學系
Department of Chemistry
論文出版年: 2023
畢業學年度: 111
語文別: 中文
論文頁數: 218
中文關鍵詞: 雜環化學銅金屬催化6π-氮雜電環化雙環化反應克腦文蓋爾縮合反應喹唑啉衍生物3-羥基 -3-呋喃基異吲哚啉酮串聯反應烏爾曼型合環反應
英文關鍵詞: heterocyclic compound, Copper catalyzed, Ullmann type reaction, 6π-Azaelectrocyclization cyclization, Double cyclization, Knoevenagel-type condensation, Quinazolin derivatives, Tandem cyclization
研究方法: 實驗設計法
DOI URL: http://doi.org/10.6345/NTNU202301328
論文種類: 學術論文
相關次數: 點閱:81下載:4
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  • 一:利用2-碘苯甲醯胺衍生物和炔丙基二羰基化合物作為起始物並利用銅催化促成氧化級聯分子間雙環化來進行3-羥基-3-呋喃基異吲哚啉酮衍生物的一鍋化合成。本次的策略包含環化反應、偶聯反應、雙C(sp3)-H官能化。本次合成3-羥基-3-呋喃基異吲哚啉酮衍生物的策略是利用不同取代基的2-碘苯甲醯胺衍和各種不同的炔丙基二羰基及炔丙基磺醯基芳基酮。
    二:我們開發出一種以溴丙烯醛、苯甲醯乙腈和乙酸銨為起始物並利用銅金屬進行催化反應歷經三個不同反應後生成三取代吡啶。3-溴丙烯醛與苯甲醯乙腈會先進行克腦文蓋爾縮合反應形成2,4-二烯酮隨後和氨進行反應,並生成相應的氮雜三烯。最後經過6π-氮雜電環化/芳構化反應並生成三取代的吡啶。
    三:我們開發出一種反應過程簡單、產率高的一鍋化方法,透過銅催化將N-(2-溴芐基)-2-碘苯甲醯胺的進行串聯反應而合成出吲哚並 [1,2-b] 喹唑啉-12(10H)-酮和氰化銅

    1.One-pot strategy is reported for the synthesis of 3-hydroxy-3-furylisoindolinone derivatives via copper catalyzed oxidative cascade inter-molecular double cyclisation of 2-iodobenzamide derivatives and propargyl dicarbonyl compounds in the presence of oxygen. The present strategy involves several reactions including cyclization/coupling/double C(sp3)-H functionalization in cascade manner. Wide range of 2-iodobenzamide substrates having different substituents as well as various propargyldicarbonyl and propargylsulfonyl aryl ketones are used to access variety of 3-hydroxy-3-furylisoindolinone derivatives in the present methodology.
    2. A facile copper-catalyzed three-component reaction for the synthesis of trisubstituted pyridines from 3-bromopropenals, benzoylacetonitriles, and ammonium acetate (NH4OAc) is developed. The Knoevenagel-type condensation of 3-bromopropenal with benzoylacetonitrile gives 2,4-dienone with strategically placed functional groups, which reacts with in situ generated ammonia to give the corresponding azatriene. A subsequent reaction sequence of 6π-azaelectrocyclization/aromatization produces a trisubstituted pyridine under the reaction conditions.
    3.Herein, we developed a simple and one pot method for the synthesis of isoindolo [1,2-b]quinazolin-12(10H)-one derivatives via copper catalyzed tandem reaction of N-(2-bromobenzyl)-2-iodobenzamide as substrate and copper cyanide. The procedure is easy, simple and the yields are good to excellent.

    目錄 謝誌 II 目錄 IV 一、2-碘苯甲醯胺衍生物和炔丙基二羰基化合物以銅金屬催化進行氧化級聯雙環化反應合成3-羥基-3-呋喃基異吲哚酮衍生物 1 1.1.1 呋喃衍生物介紹 (Furan) 3 1.1.2 3-羥基異吲哚酮衍生物介紹 (3-Hydroxyisoindolinone) 7 1.1.3 碸衍生物介紹 (Sulfone) 12 1.2 異吲哚啉酮合成方法 17 1.3 研究目標 20 1.4 實驗結果與討論 21 1.5 反應機構探討 35 1.6 結論 37 1.7 實驗方法 38 1.7.1 分析儀器及基本實驗操作 38 1.7.2 實驗步驟 40 1.8 文獻參考 42 1.9 光譜資料 46 二、以一鍋化方法進行克腦文蓋爾縮合反應/亞胺化/π-Aza 電環化合成三取代吡啶 115 2.1 吡啶衍生物介紹 (Pyridine) 116 2.2 6π-Azaelectrocyclization 合成介紹 120 2.3 研究目標 122 2.4 實驗結果與討論 123 2.5反應機構探討 127 2.6 結論 129 2.7 實驗方法 130 2.7.1分析儀器及基本實驗操作 130 2.7.2 實驗步驟 132 2.8文獻參考 133 2.9 光譜資料 136 三、以銅金屬進行串連環化異吲哚並 [1,2-b] 喹唑啉-12(10H)-酮和 5,13-二氫11H-喹唑啉 [2,3]喹唑啉-11-酮衍生物 178 3.1 喹唑啉衍生物 (Qunazoline) 179 3.2 喹唑啉合成方法 181 3.3 研究目標 184 3.4 實驗結果與討論 185 3.5 反應機構探討 189 3.6 結論 190 3.7實驗步驟 191 3.7.1分析儀器及基本實驗操作 191 3.7.2 實驗步驟 193 3.8 文獻參考 194 3.9 光譜資料 197

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