(Z)-3-(2-硝基苯亞基)-2,3-二氫-4氫-苯并[b]氧㖕-4-酮衍生物的合成及其應用在(Z)-6氫-苯并[7,8]氧㖕并[4,3-b]喹啉衍生物

Preparation of (Z)-3-(2-nitrobenzylidene)-2,3-dihydro-4H-benzo[b]oxocin-4-one Derivatives and its Application to Synthesis of (Z)-6H-benzo[7,8]oxocino[4,3-b]quinoline Derivatives

李昀靜(Li Yun-Ching)

指導教授 ： 姚清發

國立臺灣師範大學/理學院/化學系/碩士(2022年)

https://doi.org/10.6345/NTNU202201036

摘要

本篇研究主要為論述(Z)-6氫-苯並[7,8]氧㖕並[4,3-b]喹啉衍生物的合成，將其分為兩部分。第一部分是介紹喹啉及氧㖕的性質與合成方法，並藉由文獻資料構建合成策略進而產生研究目標。
第二部分則將此合成策略分成五個步驟，首先具有不同取代基的鄰硝基苯甲醛1與丁烯酮2進行森田-貝里斯-希爾曼反應生成化合物3後，再利用乙醯氯生成化合物4，接著與不同取代基的水楊醛5進行SN2反應生成化合物6，而後經由羥醛縮合反應形成具有八圓環的化合物7，最終，透過進行硝基的還原及分子內環化反應來得到(Z)-6氫-苯並[7,8]氧㖕並[4,3-b]喹啉衍生物8。

關鍵字

森田-貝里斯-希爾曼反應

並列摘要

This research mainly discusses the synthesis of (Z)-6H-benzo[7,8] oxocino[4,3-b]quinoline derivatives, which is divided into two parts. The first part is to introduce the properties and synthetic methods of quinolines and oxocines. In addition, the relevant literature on the synthesis strategy are described.
In the second part, the synthetic strategy of the preparation of oxocine derivatives consists of five steps. First, 2-nitrobenzaldehyde with different substituents 1 undergo the Morita-Baylis-Hillman reaction with butenones 2 to provide the compounds 3 which are further converted into the compound 4 after the treatment of acetyl chloride. After that, the compounds 4 undergoes the SN2 reaction with salicylaldehydes with different substituents 5 to afford the compounds 6. Furthermore, the compounds 7 with an eight-membered ring are synthesized via the intramolecular aldol condensation reactions of 6. Ultimately, the (Z)-6H-benzo[7,8]oxocino[4,3-b]quinoline derivatives 8 from 7 via the nitro group reduction are obtained by the reduction of the nitro-group and the intramolecular cyclization reaction.

並列關鍵字

Morita-Baylis-Hillman reaction

參考文獻

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