研究生: |
林冠碩 Lin, Kuan-Shuo |
---|---|
論文名稱: |
路易斯酸輔佐七員環2-烯炔醯胺及呋喃炔醯胺化合物的環化反應:稠雙環γ-內醯胺與吡咯衍生物的合成 Lewis Acid-Promoted Cyclization Reactions of Seven-Membered Ring 2-Enynamides and Ynamide-Tethered Furans : Synthesis of Fused Bicyclic γ-Lactams and Pyrrole Derivatives |
指導教授: |
葉名倉
Yeh, Ming-Chang |
學位類別: |
碩士 Master |
系所名稱: |
化學系 Department of Chemistry |
論文出版年: | 2018 |
畢業學年度: | 106 |
語文別: | 中文 |
論文頁數: | 255 |
中文關鍵詞: | 分子內環化反應 、炔醯胺分子 、三氯化鐵催化 、雙環γ-內醯胺 、金(III)催化 、吡咯衍生物 |
英文關鍵詞: | intramolecular cyclization, ynamide, iron(III)-catalyzed, bicyclic γ-lactam, gold(III)-catalyzed, pyrrole derivatives |
DOI URL: | http://doi.org/10.6345/THE.NTNU.DC.052.2018.B05 |
論文種類: | 學術論文 |
相關次數: | 點閱:128 下載:5 |
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本論文包含兩個主題,主題一:利用三氯化鐵輔佐2-烯炔醯胺七員環化合物,進行分子內環化反應,合成雙環[5.3.0]-γ-內醯胺化合物,主題二:利用三氯化金催化具有炔醯胺側鏈的呋喃化合物,進行分子內環化反應,合成吡咯衍合物。
主題一為三氯化鐵輔佐2-烯炔醯胺七員環化合物,進行分子內環化反應,合成具四個立體中心的含氯雙環[5.3.0]-γ-內醯胺化合物,此反應的優點為操作簡單、條件溫和且不需額外添加氧化劑即可合成含氯雙環[5.3.0]-γ-內醯胺化合物。
主題二探討有效率合成順式-3-芳香基取代-4-(側氧基-1-丙烯基)吡咯衍合物,在氮氣條件下,以三氯化金催化C-2位置具炔醯胺側鏈的呋喃化合物,可快速合成吡咯衍合物,此反應操作簡單、溫和條件且產率良好。
The thesis contains two topics. The first part is the synthesis of chlorinated bicyclo[5.3.0]-γ-lactams via iron(III) chloride-catalyzed intramolecular cyclization of seven-membered ring 2-enynamides. The second part is the synthesis of pyrrole derivatives via gold(III)-catalyzed intramolecular cyclization of ynamide-tethered furans.
A simple and mild process was developed for the synthesis of chlorinated bicyclo[5.3.0]-γ-lactams, possessing four stereocenters, from easily available seven-membered ring 2-enynamides. The reaction required only an inexpensive iron(III) chloride under dry air and were tolerant of aryl and heteroaryl groups at the alkyne terminus.
An efficient synthesis of 3-aryl-substituted-4-(3-oxopropen-1-yl)pyrroles is developed. Treatment of gold(III) chloride with furans containing a tethered ynamide at the C-2 position of the furan ring in toluene under nitrogen proceeds rapidly to afford pyrrole derivatives in good yields. The reactions are operationally simple and under mild reaction conditions.
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