Please use this identifier to cite or link to this item: http://hdl.handle.net/11455/96337
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dc.contributor洪豐裕zh_TW
dc.contributor.authorSzu-Wei Chenen_US
dc.contributor.author陳思暐zh_TW
dc.contributor.other化學系所zh_TW
dc.date2017zh_TW
dc.date.accessioned2018-12-17T03:58:23Z-
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dc.identifier.urihttp://hdl.handle.net/11455/96337-
dc.description.abstract1-H-Benz[f]indole-4,9-diones 3 were prepared in good yields by treating N-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)acetamide 2a with tertiary amines and using Pd(OAc)2 as the catalyst precursor in one-pot reactions and the structure of 3c was determined by single crystal X-ray diffraction methods. As revealed from the structure of 3c, the transition metal complex Pd(OAc)2 indeed catalyzed amines and 2a, which led to the formation of pyrrole through cyclization processes by fusing to the former napthoquinone framework. A mechanism was proposed after screening some relevant reaction conditions. Thereafter, similar reactions were carried out by employing primary and secondary amines as the amine sources. When primary amines are used as the reactants, the products will be either imidazolequinones or aminoquinones depending on the extent of the steric hindrance of amines. When secondary amines are used as the reactants, the products will be either indolequinone or aminoquinones again depending on the extent of the steric hindrance of amines. In addition, similar reactions were carried out by replacing tertiary amines with tertiary phosphines which led to the formation of ylide-like derivatives instead.en_US
dc.description.abstract本研究使用2-醯胺萘醌2a和三級胺做為起始物,和金屬鈀化合物在空氣下進行一鍋化反應,產生吲哚苯醌衍生物,產率都有80%左右,並且得到其中之一產物3c的晶體結構。推測反應是透過金屬鈀化合物先將三級胺活化,使三級胺上的取代基接上2-醯胺萘醌並在脫去氮後進行環化反應,產生吲哚苯醌。最後根據優選條件推出可行的反應機制。 接著也嘗試使用二級胺和一級胺做為反應物,在相同的條件下進行反應,發現當反應物是一級胺且胺的取代基立體障礙小的時候,產物為咪唑苯醌;立體障礙大時為胺基苯醌。而當反應物是二級胺時,主產物是吲哚苯醌並且產率和胺類取代基的立體障礙大小有關,立體障礙越小時,推測會有胺基化苯醌的副產物產生,因此目標產物的產率較低。 另外,也使用三級磷來做為反應物,在相同條件下進行反應,得到的產物則為一種有類似苯醌結構且含有碳-磷雙鍵的ylide(葉立德或鎓內鹽)。zh_TW
dc.description.tableofcontents目錄 摘要 i Abstract ii 目錄 iii Scheme 目錄 v Figure 目錄 vii Table 目錄 viii 第一章 序論 1 第一節 Indole-4,7-quinone簡介 2 第二節 C-H鍵活化反應(C-H functionalization reaction)簡介 6 第三節 Quinone上C-H鍵活化反應簡介 8 第四節 研究方向 12 第二章 實驗 15 第一節 儀器與設備 16 第二節 藥品 19 第三節 合成與鑑定 21 第三章 結果與討論 32 第一節 Amido-substituted napthoquinone與三級胺的反應 33 第二節 Amido-substituted napthoquinone與一級胺的反應 47 第三節 Amido-substituted napthoquinone與二級胺的反應 51 第四節 Amido-substituted napthoquinone與三級磷的反應 53 第四章 結論 56 第五章 參考文獻 57 第六章 附錄 64 第一節 光譜數據 65 第二節 晶體數據 93zh_TW
dc.language.isozh_TWzh_TW
dc.rights同意授權瀏覽/列印電子全文服務,2017-08-21起公開。zh_TW
dc.subject碳-氫活化zh_TW
dc.subject鈀催化zh_TW
dc.subject合環zh_TW
dc.subject萘醌zh_TW
dc.subject?咯zh_TW
dc.subject醯胺zh_TW
dc.subjectC-H functionalizationen_US
dc.subjectPalladiumen_US
dc.subjectcyclizationen_US
dc.subjectNaphthoquinoneen_US
dc.subjectPyrroleen_US
dc.subjectAmideen_US
dc.subjectPhosphineen_US
dc.titlePalladium-Catalyzed C-H Functionalization of Amido-substitued 1,4-Napthoquinone in the Presence of Amines Toward the Formation of Pyrroles and Imidazolesen_US
dc.title醯胺萘醌在鈀金屬催化下和胺類進行碳-氫鍵活化反應產生吡咯及咪唑衍生物zh_TW
dc.typethesis and dissertationen_US
dc.date.paperformatopenaccess2017-08-21zh_TW
dc.date.openaccess2017-08-21-
item.languageiso639-1zh_TW-
item.openairetypethesis and dissertation-
item.cerifentitytypePublications-
item.grantfulltextrestricted-
item.fulltextwith fulltext-
item.openairecristypehttp://purl.org/coar/resource_type/c_18cf-
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