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

Date
2011
Authors
林占杰
Chan-Chieh Lin
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Abstract
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.
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Keywords
吲哚, 喹啉, indole, quinoline
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