壹、以水相反應合成萘醌衍生物 貳、利用森田-貝里斯-希爾曼產物合成(Z)-6氫-苯並[7,8]硫㖕並[4,3-b]喹啉與其衍生物

Abstract

本論文分為兩個部份，每個部分各自獨立，包括前言、研究目標、實驗結果與討論，以及結論。 第一部份是以指甲花醌與β-硝基苯乙烯在以四丁基溴化銨作為相轉移催化劑的條件下，以水取代有機溶劑，經由水相反應合成出萘醌類衍生物。 第二部份是以三步反應合成出8元環硫化物(Z)-6氫-苯並[7,8]硫㖕並[4,3-b]喹啉與其衍生物。第一步以森田-貝里斯-希爾曼反應產物與具有硫乙醯官能基的苯甲醛進行親合取代反應得到中間產物，第二步再以此中間產物進行分子內曼尼希反應得到具有8元環的硫化物中間體，最後再以中間體一鍋化得進行還原反應與環加成反應得到最終產物。

This thesis is divided into two parts, each of which is independent of each other, including the preface, research objectives, results and discussions, and conclusion. The first part is the synthesis of naphthoquinone derivatives from Lawson react with β-nitrostyrene via in water reaction by using tetrabutylammonium bromide as phase transfer catalyst. The second part is the synthesis of 8-membered ring thiocompound, (Z)-6H-benzo[7,8]thiocino[4,3-b]quinoline and its derivatives in a three-step reaction. In the first step, the Morita-Baylis-Hilliman reaction adducts react with benzaldehydes which have a thioacetate functional group via nucleophilic substitution. In the second step, the intermediate is subjected to an intramolecularmannich reaction to obtain eight-membered ring intermediate. In the final step, the intermediate is subjected to a one-pot reaction with reduction and cycloaddition to obtain the final product.