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| 研究生： |
陳盈妤 Chen, Ying-Yu |
|---|---|
| 論文名稱： |
醯胺衍生物的分子內環化反應於合成多取代2-喹啉酮及2-吲哚酮類化合物之研究 Synthesis of Highly Substituted 2-Quinolinones and 2-Indolones via Intramolecular Cyclization of Amide Derivatives |
| 指導教授： |
莊治平
Chuang, Che-Ping |
| 學位類別： |
碩士 Master |
| 系所名稱： |
理學院 - 化學系 Department of Chemistry |
| 論文出版年： | 2017 |
| 畢業學年度： | 105 |
| 語文別： | 中文 |
| 論文頁數： | 132 |
| 中文關鍵詞： | 自由基 、醋酸鈷(II) 、碸基自由基 、2-喹啉酮 、2-吲哚酮 |
| 外文關鍵詞： | Free radical, Cobalt(II) acetate, p-Toluenesulfonyl radical, 2-Indolones |
| 相關次數： | 點閱：116 下載：0 |
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自由基反應在有機合成中扮演著重要的角色，利用過渡金屬催化搭配自由基與不飽和鍵環合被認為是合成雜環化合物非常有用的途徑，常利用的金屬離子有錳、鎳、鈷、銅等，其中鈷具有成本低廉且對環境友善的特性。另外，碸基自由基(sulfonyl radical)可與不飽和鍵進行加成，生成自由基中間體再進一步反應，普遍常見利用醋酸錳(III)或是銀(I)催化劑來進行。
本論文分為兩部分，第一部分是利用醋酸鈷(II)搭配過氧化叔丁醇進行分子內自由基環合反應合成2-喹啉酮類化合物。
第二部分是利用對甲苯磺酸鈉鹽搭配過硫酸鉀與碸基化合物，作為碸基自由基的來源與醯胺碸基化合物進行分子內自由基環合反應合成2-吲哚酮類化合物。
We have developed an efficient synthesis of 2-quinolinones by using a cobalt(II) acetate-catalyzed carbocyclization reaction of α-bromo-N-phenylacetamide derivatives employing TBHP (tert-butyl hydroperoxide) as an oxidant. This reaction is applicable to a wide range of substrates with different electronic properties. And is also a more convenient way for 2-indolones systhesis. 2-Indolones can be produced by carbamoylmeththyl radical, generated from the p-toluenesulfonyl radical induced reaction of allylsulfonyl-N-arylethanamide, undergoing a ring cyclization, and followed by aromatization. This reagent affords extremely easy workup and affords high yields of product.
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校內：2022-06-28公開校外：不公開