臺灣博碩士論文加值系統

第一部份、香豆素和吡啶并[2,1-a]異喹啉稠合雜環及其衍生物之合成

含有黃連素骨架之化合物是目前已被廣泛研究的一種具有豐富生物活性之生物鹼，例如：抗菌、抗發炎、抗瘧疾以及抗腫瘤。以前的合成大多是集中在黃連素的生物學及醫療之應用，較少去探索其光化學性質，本研究利用帶有多種藥學及光化學性質之香豆素與喹啉進行稠合，期望合成得類似於黃連素骨架之系列衍生物，並探討其結構上之功能性性質、光敏感性質以及潛在生物活性。

第二部份、多組成合成(3E)-3-[烷基胺(芳基)亞甲基]唍
-2,4-二酮化合物及-硝基醯胺衍生物

本論文主要探討硝基甲烷促進一鍋化三組成反應合成 (3E)-3-[烷基胺(芳基)亞甲基]唍-2,4-二酮化合物，以及硝基甲烷參與反應促進一鍋化四組成反應合成-硝基醯胺衍生物，此二系列合成已經由核磁共振氫譜及碳譜圖與X-ray晶體分析證明結構之正確性，並藉由實驗結果推測兩者的反應機構途徑不同，最後對兩種多組成反應進行官能基之修飾，合計獲得24個不同官能基之化合物，-硝基醯胺衍生物方面則獲得3個化合物。

Part I、Synthesis of Coumarin-fused Pyrido[2,1-a]isoquinolin
-8-ium Heterocycles and Their Derivatives

Protoberberines are alkaloids that exhibit a wide range of biological activities such as antimicrobial, anti-inflammatory, antimalarial, and antitumor. Previous synthetic efforts have been primarily focused on the biological and therapeutic applications of protoberberines, their intrinsic photochemical properties were much less explored. In this study, a coumarin and pyrido[2,1-a]isoquinolin-8-ium-fused heterocycles were synthesized by p-TsOH-mediated coupling of 3-formylcoumarins and dihydroisoquinolines. The prepared compounds were further subjected to based-mediated ring opening and subsequent photochemical electrocyclization to investigate their potential functional properties. The synthetic details, structural characterization and photochemical properties of the prepared compounds were described.

Part II、Multicomponent Synthesis of (3E)-3-[Alkylamino(aryl)methylidene]chroman-2,4-diones
and -Nitro Amide Derivatives

We have developed the nitromethane-mediated synthesis of (3E)-3-[alkylamino(aryl)methylidene]chroman-2,4-dione by one-pot three-component reaction and nitromethane-mediated synthesis of -nitro amide deriviates by one-pot four-component reaction in this thesis. Their molecular structures were characterized by 1H and 13C NMR spectra and X-ray crystal analysis. The mechanisms for the two reactions were proposed. Finally, the scope of the two multicomponent reactions were explored. Twenty four derivatives of (3E)-3-[alkylamino(aryl) methylidene]chroman-2,4-dione and three derivatives of -nitro amide were obtained.

第一部份、香豆素和吡啶并[2,1-a]異喹啉稠合雜環及其衍生物之合成

第一章、 緒論…………………………………………………….……2
1.1 香豆素………………………………………………………...2
1.2 黃連素………………………………………………………...4
第二章、 研究動機…………………………………………………….5
2.1 設計含香豆素及喹啉稠合之黃連素衍生物………………...5
第三章、 結果與討論……………………………………………….…7
3.1 設計含香豆素及喹啉稠合之黃連素衍生物……….………..7
第四章、 結論………………………………………………………...17
第五章、 實驗部分…………………………………………………...18
5.1 儀器部份及試藥來源…………………………………….…18
5.2 化合物的合成……………………………………………….19
第六章、 參考文獻…………………………………………….……...28
第七章、 圖譜資料……………………………………………….…...30

第二部份、多組成合成(3E)-3-[烷基胺(芳基)亞甲基]唍
-2,4-二酮化合物及γ-硝基醯胺衍生物

第一章、 緒論………………………………………………….……....52
1.1 -烯胺酮………………………………………………….…...52
1.2 -硝基醯胺…………………………………………….……...53
1.3 多組成反應……………………………………………….…..54
第二章、 研究動機…………………………………………….…..…..57
2.1 設計三組成反應合成-烯胺酮衍生物…………………...…57
第三章、 結果與討論……………………………………………...…..59
3.1以一鍋化三組成反應製備 (3E)-3-[烷基胺(芳基)亞甲基]唍
-2,4-二酮探討…………………………………………..….....59
3.2以一鍋化四組成反應製備-硝基醯胺衍生物………….…...64
第四章、 結論…………………………………………………..…...…68
第五章、 實驗部分……………………………………………..…...…69
5.1 儀器部份及試藥來源…………………………………..….…69
5.2 化合物的合成…………………………………………….…..70
第六章、 參考文獻………………………………………………..…...87
第七章、 圖譜資料………………………………………………..…...89

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