Please use this identifier to cite or link to this item: http://rportal.lib.ntnu.edu.tw:80/handle/20.500.12235/100433
Title: (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
Authors: 簡敦誠
廖本原
Keywords: 醯胺肟
苯併咪唑
一價銅催化
吲哚
carboxamidoxime
benzimidazole
copper (I) catalyst
indole
Issue Date: 2014
Abstract: 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.
URI: http://etds.lib.ntnu.edu.tw/cgi-bin/gs32/gsweb.cgi?o=dstdcdr&s=%22http://etds.lib.ntnu.edu.tw/cgi-bin/gs32/gsweb.cgi?o=dstdcdr&s=id=%22GN060142041S%22.&%22.id.&
http://rportal.lib.ntnu.edu.tw:80/handle/20.500.12235/100433
Other Identifiers: GN060142041S
Appears in Collections:學位論文

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