簡敦誠廖本原2019-09-04不公開2019-09-042014http://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.醯胺肟苯併咪唑一價銅催化吲哚carboxamidoximebenzimidazolecopper (I) catalystindole