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研究生:莊新毅
研究生(外文):Xin-Yi Zhuang
論文名稱:探討不同芳香基取代高價碘試劑誘導苯胺與吡啶進行分子間碳-氮鍵偶合反應合成Benzo[4,5]imidazo[1,2-a]pyridine與其衍生物
論文名稱(外文):Synthesis of Benzo[4,5]imidazo[1,2-a]pyridine and its derivatives by intermolecular carbon-nitrogen bond coupling reaction between aniline and pyridine induced by different aromatic substituted hypervalent iodine reagents
指導教授:吳明忠
指導教授(外文):Ming-Jung Wu
學位類別:碩士
校院名稱:國立中山大學
系所名稱:化學系研究所
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2019
畢業學年度:107
語文別:中文
論文頁數:156
中文關鍵詞:分子間環化苯并[45]咪唑并[12-a]吡啶不同取代基高價碘試劑苯胺衍生物吡啶衍生物
外文關鍵詞:different substituents highpervalent iodine reagentsBenzo[45]imidazo[12-a]pyridinepyridine derivativesAniline derivativesintermolecular cyclization
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在本文中,我們成功的找到同類型不同之取代基團之高價碘試劑:(4-methoxyphenyl)- λ3-iodanediyl diacetate與 (4-methoxyphenyl)- λ3-iodanediyl diacetate,提高誘導苯胺衍生物與吡啶衍生物生成Benzo[4,5]imidazo[1,2-a]pyridine骨架化合物之反應產率,所有反應產率皆坐落在50%至80%之間,另外提供了兩種高價碘試劑與產物的結構,利用了x-ray單晶繞射技術進行確認,另外在藥物領域上具有前瞻性,故我們也希望透過此簡易的合成方式來量產這類型化合物,能夠迅速地提供本化合物之骨架。
  In this thesis, we have successfully found two types of highpervalent iodine reagents with different substituent groups: (4-methoxyphenyl)- λ3-iodanediyl diacetate and (4-methoxyphenyl)- λ3-iodanediyl diacetate, increasing the yield of the production of benzo[4,5]imidazo[1,2-a]pyridines with aniline derivatives and pyridine derivatives as starting materials.
  In this thesis, we have successfully found two types of highpervalent iodine reagents with different substituent groups: (4-methoxyphenyl)- λ3-iodanediyl diacetate and (4-methoxyphenyl)- λ3-iodanediyl diacetate, increasing the yield of the production of benzo[4,5]imidazo[1,2-a]pyridines with aniline derivatives and pyridine derivatives as starting materials.
  Compounds with benzo[4,5]imidazo[1,2-a]pyridine skeletons are compound is obtained, and the yields are between 50% and 80%. Furthermore, the structures of two products and highpervalent iodine reagents are provided.
  The structures are confirmed by the x-ray single crystal diffraction technique, and are also promising in the pharmaceutical industry. Therefore, we also hope we are able to rapidly produce the compounds possessing this structure with the facile synthetic strategy herein.
索引目錄 頁碼
論文審定書……………………………………………………………………………………………………………….i
公開授權書……………………………………………………………………………ii
謝誌 ……………………………………………………………………………………………………………………….iii
中文摘要 ……………………………………………………………………………………………………………….iv
英文摘要 …………………………………………………………………………………………………………………v
第一章、緒論…………………………………………………………………………………………………………….1
1-1高價碘試劑的介紹………………………………………………………….......1
1-2高價碘試劑的出現對於交叉偶合反應的優勢……………………………4
1-3高價碘於有機合成中的應用………………………………………………6
1-3-1高價碘試劑在氧化反應中的應用…………………………………….6
1-3-2高價碘化合物在加成中的反應……………………………………….9
1-3-3高價碘化合物於取代中的反應………………………………………10
1-3-4高價碘化合物於重排中的反應………………………………………11
1-3-5高價碘化合物於天然物方面的應用…………………………………13
1-4 Benzo[4,5]imidazo[1,2-a]pyridine…………………………………………15
第二章、主文.................................................................................................................25
2-1研究動機.......................................................................................................25
2-2反應條件篩選之回顧…………………..………………………………….25
2-3高價碘試劑之篩選……………………………………………………… ..27
2-4 官能基耐受性測試之實驗成果討論…………………………………….29
2-5結論………………………………………………………………………..36
第三章、實驗部分.........................................................................................................37
3-1儀器...............................................................................................................37
3-2試藥………………..………………..……………………………………...38
3-3高價碘試劑之製備……………………………………………………… ..41
3-4三大類型反應之實驗流程………………………………………………...42
第四章、參考文獻.........................................................................................................45
第五章、附錄………………………………………………………………………….48
5-1光譜數據與物理性質...................................................................................48
5-2X-ray單晶繞射數據 ……………………………………………………...64

第六章、光譜附錄……………………………………………………...……………118
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