Author: |
洪紹豪 Hong, Shao-Hao |
---|---|
Thesis Title: |
利用膦試劑誘導生成季鏻鹽以合成雙雜環化合物及呋喃[3,2-c]香豆素衍生物 Preparation of Bis-heterocycles and Furo[3,2-c]coumarins via Phosphonium Salt Intermediates |
Advisor: |
林文偉
Lin, Wen-Wei |
Degree: |
碩士 Master |
Department: |
化學系 Department of Chemistry |
Thesis Publication Year: | 2015 |
Academic Year: | 104 |
Language: | 中文 |
Number of pages: | 550 |
Keywords (in Chinese): | 膦試劑 、鏻鹽 、雙雜環化合物 、呋喃香豆素 、Wittig 反應 |
Keywords (in English): | phosphine, phosphonium salt, bis-heterocycles, furocoumarin, Wittig reaction |
Thesis Type: | Academic thesis/ dissertation |
Reference times: | Clicks: 248 Downloads: 0 |
Share: |
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第一章:利用吲哚、水楊醛及醯氯行縮合/醯化/Wittig連鎖反應,在酸以及膦試劑的誘導下可以成功地合成吲哚-苯并呋喃加成物。此反應所需條件十分溫和,不需使用過渡金屬催化,起始物也不需預先處理或活化,為一合成雙雜環化合物的新路徑。反應中所生成的中間體為可簡單分離並純化的穩定季鏻鹽,是一具有潛力的Wittig試劑。
第二章:利用查耳酮香豆素作為起始物,與膦試劑及醯氯反應後可有效率地得到應用性多元的季鏻鹽中間體,其可加入飽和碳酸氫鈉水溶液切除膦試劑,得到呋喃[3,2-c]香豆素產物;亦可加入鹼及高活性的羰基化合物並進行分子間Wittig反應,得到具有烯烴的呋喃[3,2-c]香豆素產物。此法的反應條件十分溫和,可在短時間內得到預期產物。
Chapter I: An acid-mediated condensation/acylation/Wittig tandem reaction between indoles, salicylaldehyde dericatives and acyl chlorides to generate indole-benzo[b]furan adducts is described. This highly efficient approach towards such bis-heterocyclic compounds via easily accessible phosphonium salt intermediates has not been reported. Under metal-free reaction conditions and without preactivation of the coupling partners, this synthetic strategy provides the desired products in moderate to good yields in a two-step procedure. Furthermore, we also developed a protocol in a one-pot approach with the only slightly diminished yield of the desired adduct.
Chapter II: A Bu3P-mediated cyclisation reaction of 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones via electrophilic addition of acyl chlorides towards the synthesis of highly functionalized furo[3,2-c]coumarins bearing a phosphorus ylide moiety is described. These unprecedented cyclisation reactions proceed under mild reaction conditions within short reaction times (1 min to 1 h), and can be further applied in the synthesis of alkenyl-substituted furo[3,2-c]coumarins after the treatment with carbonyl electrophiles under basic condition.
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