- 學位論文
2-和3-(2-苯並[b]硒吩並)吲哚的狄耳士–阿德爾反應探討及喹喔啉衍生物的光學性質
Study of the Diels–Alder reaction of 2- and 3-(2-benzo[b]selenolo)indole and the photophysical properties of Quinoxaline derivatives
摘要
吲哚衍生物 (AHACs) 在許多文獻中已經被報導具有許多生物活性，如抗菌、抗真菌和抗腫瘤活性等等；而硒為人體不可或缺的元素之一，缺乏硒會造成像是克山病、溪山症這類疾病。 本論文利用金屬催化如Sonogashira反應、Glaser反應，合成吲哚旁接有(2-溴苯基)乙炔基的結構，再利用SNAr反應合環得到尚未報導過的結構2-和3-(2-苯並[b]硒吩並)吲哚。接著利用結構上的共軛雙烯位置與親二烯試劑如馬來醯亞胺、Diethyl Acetylenedicarboxylate 進行Diels–Alder反應，探討其反應性，並企圖合成出AHACs這類的仿天然物結構。 喹喔啉衍生物在藥物上有許多生物活性，如治療HIV、抑制分枝桿菌等等，在材料上也有被拿來用作DSSCs的研究。 本論文使用各類含醛基化合物，與丁二酮進行羥醛縮合反應，合成出一系列Cinnamils，接著將得到的Cinnamils與鄰苯二胺反應脫水後，形成喹喔啉衍生物。最後探討不同官能基對吸收與放射光譜的影響。
並列摘要
Indole derivatives (AHACs) have been reported in many literatures with many biological activities, such as antibacterial, antifungal and antitumor activities. And selenium is one of the indispensable elements of the human body, selenium deficiency can cause Keshan Disease and Kashin Beck̕ s disease. Applied metal catalyzed reaction such as Sonogashira reaction and Glaser reaction to synthesize 2 and 3-((2-bromophenyl)ethynyl)-1H-indole, and followed by cyclization to form 2- and 3- (2-benzo[b]) indole via SNAr reaction. Then, reacted of the dienophile reagent with 2- and 3- (2-benzo[b]) indole by Diels–Alder reaction. Dienophile reagent used in this report including maleimide and diethyl Acetylenedicarboxylate. Quinoxaline derivatives are with biological activities, such as anti-HIV and antibacterial. It is also used in DSSCs on materials. Treatment of series of aldehyde-containing compounds with butanedione gave various Cinnamils. After that, condensation of cinnamils with 1,2-diaminobenzene afforded Quinoxaline derivatives. The photophysical properties of Quinoxaline derivatives were studied.
參考文獻
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