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Author: 林占杰
Chan-Chieh Lin
Thesis Title: 便宜而有效合成吲哚及喹啉類化合物方法之研究
Efficient and Cost-Effective Protocols for the Synthesis of Hexahydrocyclohepta[b]indoles and 4-(1H-indol-3-yl)quinolines
Advisor: 姚清發
Yao, Ching-Fa
Degree: 碩士
Master
Department: 化學系
Department of Chemistry
Thesis Publication Year: 2011
Academic Year: 99
Language: 中文
Number of pages: 470
Keywords (in Chinese): 吲哚喹啉
Keywords (in English): indole, quinoline
Thesis Type: Academic thesis/ dissertation
Reference times: Clicks: 134Downloads: 4
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  • 本論文第壹部分討論使用便宜且容易取得之試劑,例如N-溴代丁二醯亞胺及碘來催化吲哚與二苄叉丙酮進行二次麥可加成反應,產物為具吲哚架構之吲哚[6-5-7]環衍生物;根據文獻報導指出,吲哚[6-5-7]環衍生物,具有廣泛的生物與藥物活性,因此也希望本實驗產物能具有發展的潛力。
    本論文第貳部分討論使用有效且高產率的方法,合成4-吲哚喹啉架構之衍生物。首先,以磺胺酸催化麥可加成反應,將吲哚引入反-2-硝基查爾酮,之後再以鐵金屬還原硝基並促使合環形成喹啉環。反應實驗中亦發現,由於立體障礙的影響會出現以碳原子為離去基的脫去反應;文獻報導亦指出,4-吲哚喹啉衍生物可能具有治療氣喘、過敏性鼻炎、和其他發炎相關疾病的潛力。
    關鍵字:吲哚

    This thesis is divided into two parts. The first part of this thesis described an expedient protocol for the synthesis of hexahydrocyclohepta[b]indole derivatives via double Michael addition by using inexpensive and commercially available N-bromosuccinimide (NBS) and iodine as catalysts. NBS catalyzed the Michael addition of indole and the step of cyclization was catalyzed by iodine. Hexahydrocyclohepta[b]indole derivatives are important as they possess great biological and pharmacological activities.
    The second part of the thesis deals with a facile route for the synthesis of 4-(1H-indol-3-yl)quinoline derivatives by using a handy reducing reagent (Fe/HCl). The reaction proceeded via reduction of nitro functionality into amine functionality and it was followed by cyclization and aromatization. A mechanism is postulated, for the conversion, on the basis of experimental outcomes and literature reports.

    中文摘要 Ⅰ 英文摘要 Ⅱ 壹、 以N-溴代丁二醯亞胺與碘進行二次麥可加成反應合成吲哚衍生物之研究 1.1 前言 3 1.1.1 吲哚與其衍生物的介紹 3 1.1.2 麥可加成反應 7 1.1.3 N-溴代丁二醯亞胺與碘 9 1.2 研究動機 12 1.3 研究策略與構想 13 1.4 實驗結果與討論 14 1.4.1 N-溴代丁二醯亞胺催化吲哚與二苄叉丙酮的反應 14 1.4.2 使用碘催化分子內合環反應 20 1.4.3 一鍋化反應以合成[6-5-7] ring衍生物 26 1.4.4 反應機構的探討 32 1.5 結論 32 1.6 實驗部分 33 1.6.1 實驗步驟 33 1.6.2 實驗方法 34 1.6.3 光譜資料 35 1.7 參考文獻 60 附錄 63 1H-NMR、13C-NMR光譜附圖 63 X-ray單晶繞射 213 貳、 藉由鐵促使合環反應合成具4-吲哚喹啉架構衍生物之研究 2.1 前言 245 1.1.1 喹啉與其衍生物的介紹 245 1.1.2 喹啉與其衍生物的合成 246 1.1.3 喹啉-吲哚衍生物的介紹 247 2.2 研究策略與構想 248 2.3 實驗結果與討論 249 2.3.1 磺胺酸催化吲哚與反-2-硝基查爾酮反應的探討 249 2.3.2 鐵與氯化氫共同促使化合物3的合環反應 253 2.3.3 化合物7的延伸應用 261 2.3.4 反應機構的探討 267 2.4 結論 271 2.5 實驗部分 272 2.5.1 實驗步驟 272 2.5.2 實驗方法 273 2.5.3 光譜資料 274 2.6 參考文獻 298 附錄 299 1H-NMR、13C-NMR光譜附圖 299 X-ray單晶繞射 423

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