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系統識別號 U0002-3107201212144800
中文論文名稱 有機錫類化合物與疊氮化物進行”Click”反應合成三氮二烯五環化合物 [2+2+2]-環化反應合成含氮多環芳香族化合物
英文論文名稱 Click Reaction of Alkynyl Stannane with Aryl Azide And Synthesis of N-Polyaromatic Compounds via [2+2+2]-Cycloaddition Reaction
校院名稱 淡江大學
系所名稱(中) 化學學系碩士班
系所名稱(英) Department of Chemistry
學年度 100
學期 2
出版年 101
研究生中文姓名 林育祥
研究生英文姓名 Yu-Hsiang Lin
學號 699180054
學位類別 碩士
語文別 中文
第二語文別 英文
口試日期 2012-05-31
論文頁數 104頁
口試委員 指導教授-李世元
委員-林啟萬
委員-陳錦地
中文關鍵字 Click 化學  [2+2+2]環化反應 
英文關鍵字 Click Chemistry  [2+2+2]-Cycloaddition 
學科別分類 學科別自然科學化學
中文摘要 部分一:
三氮二烯五環化合物通常具生物活性用以抗菌或抗HIV病毒。我們將含鹵素基的雜環先行合成含有各種不同官能基的疊氮化物,再與有機錫官能基的炔類進行”Click”反應,可合成具有機錫官能基的三氮二烯五環化合物。有機錫官能基可以藉由其它已知反應來生成更多樣化的衍生物,使其在合成上具更高的應用性。

部分二:
含氮多環芳香族化合物的衍生物通常具有生物活性用來抗癌及抗菌等功能,我們以2-乙炔基苯甲醛與鹵素芳香族化合物進行偶合反應,或以2-溴苯甲醛與末端炔芳香族化合物進行偶合反應,再以巴比艾爾型式反應將丙炔基鹵化物對醛類進行加成反應來合成加碳炔丙基醇化合物。將加碳炔丙基醇化合物與氰化苯進行[2+2+2]-環化反應,即可合成含氮多環芳香族化合物。
英文摘要 Part I:
[1,2,3]-Triazoles often exhibit biological activity which may be used as antibacterial or anti-HIV drug.Aryl halides were converted to a variety of aryl azide and which were further reacted with alkynyl stannane by “Click” reaction to produce triazole compounds.

Part II:
Nitrogen-containing polycyclic aromatic compounds generally exhibit biologically activities such as anti-cancer or anti-bacterial activities.The coupling reaction of 2-ethynylbenzaldehyde with various haloaromatic compounds or the coupling reaction of 2-bromobenzaldehyde with a variety of terminal alkynes can produce alkynyl benzaldehydes.
The alkynyl benzaldehyde was reacted with propargyl bromide via Barbier-type reaction to generate the expected alkynyl homopropargyl alcohol.
The alkynyl homopropargyl alcohol was reacted with phenylcyanide to afford nitrogen-containing polyaromatic compounds by [2+2+2]-cycloaddition reaction.
論文目次 目錄
第一部分:有機錫類化合物與疊氮化物進行”Click”
反應合成三氮二烯五環化合物
第一章 緒論……………………………………………………....….1
1-1 三氮二烯五環化合物的重要性……………………….……..2
1-2 三氮二烯五環化合物的應用性…………………….………..3
1-3 三氮二烯五環化合物的合成方法……………………….…..9
第二章 結果與討論……………………………………….............15
2-1 三氮二烯五環化合物的合成…………………….…………15
2-2 結論………………………………………………………….19
第三章 儀器與實驗步驟…………………………………………20
3-1 實驗步驟…………………………………………………….20
3-2 實驗儀器…………………………………………………….25
3-3 溶劑的乾燥………………………………………………….27
第二部分:[2+2+2]-環化反應合成含氮多環芳香族化合物
第四章 緒論………………………………………………………...28
4-1 含氮多環芳香族化合物的重要性………………………….29

VI
4-2 含氮多環芳香族化合物的衍生物應用…………………….31
4-3 含氮多環芳香族化合物的衍生物合成方法……………….33
4-4 [2+2+2]-環化反應的應用…………………..………………41
第五章 結果與討論……………………………………………….46
5-1 超音波誘導巴比艾爾型式反應製備起始化合物………….46
5-2 合成各種含氮多環芳香族化合物的衍生物……………….48
5-3 結論………………………………………………………….54
第六章 儀器與實驗步驟…………………………………………55
6-1 實驗步驟…………………………………………………….55
6-2 實驗儀器…………………………………………………….59
6-3 溶劑的乾燥………………………………………………….61
第七章 光譜……………………………………………………...…62
參考資料……………………………………………………………..103

Scheme 目錄
Scheme 1-2-1 …………………………………………………..3
Scheme 1-2-2 …………………………………………………..5
Scheme 1-2-3 …………………………………………………..6
Scheme 1-2-4 …………………………………………………..6
Scheme 1-2-5 …………………………………………………..7
Scheme 1-2-6 …………………………………………………..8
Scheme 1-2-7 …………………………………………………..8
Scheme 1-3-1 …………………………………………………..9
Scheme 1-3-2 ………………………………………..………..10
Scheme 1-3-3 …………………………………………………10
Scheme 1-3-4 …………………………………………………11
Scheme 1-3-5 …………………………………………………12
Scheme 1-3-6 …………………………………………………13
Scheme 1-3-7 …………………………………………………14
Scheme 2-1-1 …………………………………………………15
Scheme 2-1-2 …………………………………………………16
Scheme 2-1-3 …………………………………………………16

VIII
Scheme 2-1-4 …………………………………………………17
Scheme 2-1-5 …………………………………………………17
Scheme 2-1-6 …………………………………………………18
Scheme 2-1-7 …………………………………………………18 Scheme 4-1-1 …………………………………………………29
Scheme 4-1-2 …………………………………………………30
Scheme 4-2-1 …………………………………………………31
Scheme 4-2-2 …………………………………………………32
Scheme 4-3-1 …………………………………………………33
Scheme 4-3-2 …………………………………………………34
Scheme 4-3-3 …………………………………………………35
Scheme 4-3-4 …………………………………………………36
Scheme 4-3-5 …………………………………………………37
Scheme 4-3-6 …………………………………………………38
Scheme 4-3-7 …………………………………………………39
Scheme 4-3-8 …………………………………………………40
Scheme 4-4-1 …………………………………………………41
Scheme 4-4-2 …………………………………………………42

IX
Scheme 4-4-3 …………………………………………………42
Scheme 4-4-4 …………………………………………………43
Scheme 4-4-5 …………………………………………………44
Scheme 4-4-6 …………………………………………………44
Scheme 4-4-7 …………………………………………………45
Scheme 5-1-1 …………………………………………………47
Scheme 5-2-1 …………………………………………………48
Scheme 5-2-2 …………………………………………………49
Scheme 5-2-3 …………………………………………………50
Scheme 5-2-4 …………………………………………………51
Scheme 5-2-5 …………………………………………………52
Scheme 5-2-6 …………………………………………………52
Scheme 5-2-7 …………………………………………………53
Scheme 5-2-8 …………………………………………………53
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