研究生: |
廖本原 |
---|---|
論文名稱: |
(1) Benzimidazoles的合成研究 (2) 銅金屬催化Indoles的合成研究 (1) Synthetic Studies of Benzimidazoles from Amidoximes (2) Copper-Catalyzed Synthesis of Indoles |
指導教授: | 簡敦誠 |
學位類別: |
碩士 Master |
系所名稱: |
化學系 Department of Chemistry |
論文出版年: | 2014 |
畢業學年度: | 102 |
語文別: | 中文 |
論文頁數: | 112 |
中文關鍵詞: | 醯胺肟 、苯併咪唑 、一價銅催化 、吲哚 |
英文關鍵詞: | carboxamidoxime, benzimidazole, copper (I) catalyst, indole |
論文種類: | 學術論文 |
相關次數: | 點閱:186 下載:0 |
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本篇論文分為兩個部分,第一部分為合成在胺基上具有不同取代基的雜環carboxamidoxime,並以此carboxamidoxime為起始物,利用p-toluenesulfonic anhydride作為sulfonyllating 試劑,在低溫下進行親電性芳香環取代反應,得到2位具有雜環的bezimidazole衍生物。另外,我們亦探討carboxamidoxime在不同的sulfonylating 試劑下進行Tienmann 重排反應而形成N,N’-雙取代urea衍生物。
第二部分為3-cyanoindole衍生物的合成研究,以鄰位有鹵素的aniline或是benzonitrile作為起始物,合成出N-(o-ethynylphenyl)-N-toylcyanamide衍生物。最後在銅催化下得到合環的3-cyanoindole衍生物。
This thesis covers two separated topics. The first part is the synthesis of N-phenyl hetero-aryl carboxamidoximes with different substituents on the bezene ring. The reaction of the N-phenyl hetero-aryl carboxamidoximes with p-toluenesulfonic anhydride undergoes a direct intramolecular electrophilic aromatic substitution at low temperature, to afford 2-hetero-arylbenzimidazole derivatives. Moreover, we also found that the reaction of arylcarboxamidoximes with different sulfonyl reagents undergo Tiemann rearrangement reaction to afford corresponding of N,N’-disubstituted ureas.
The second part focuses on studying the synthesis of 3-cyanoindole derivatives. N-(o- ethynylphenyl)- N-tosylcyanamide derivatives were prepared from corresponding o-haloanilines or o-halobenzonitrile. 3-Cyanoindole derivatives were obtained when treatment of o-ethynylphenyl cyanamides with a catalytic amount of CuI.
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50. 國立臺灣師範大學,林嘉祺,101年
51. 國立臺灣師範大學,謝宗翰,102年