利用Friedel-Craft acylation及一鍋化的方式來合成thiochroman-4-ones衍生物; 利用微波催化合成3-(1-(thiol)ethyl)-1H-indoles衍生物

Abstract

本論文主要分為兩個部分，第一部分介紹屬於一鍋化而簡易的合 成方式來合成thiochroman-4-one 衍生物，起始步驟為使用芳香類硫酚進行麥可加成至丙烯酸上形成β-arylthiopropanoic acids，接著加入路易士酸以催化分子內Friedel-Crafts 醯基化反應，此反應可以得到相當高產率的化合物thiochroman-4-one，應用上述產物可以進而合成出抗真菌藥劑(Z)-3-(4-methoxy benzylidene)-thiochroman-4-one。 第二部分是敘述合成3-(1-thio)ethyl-1H-indoles 吲哚類衍生物的方法，此反應是在使用二甲基甲醯胺為溶劑以及使用微波加熱至150°C 的條件下進行，反應步驟是先以芳香類硫酚進行麥可加成至3- 吲哚丙烯酸上，接著反應過程中會進行去羧基化反應進而產生高產率 的單一產物。 This thesis is mainly divided into two parts. Chapter one illustrates a convenient procedure for the one-pot synthesis of thiochroman-4-one derivatives. The initial step involves the Michael addition of aromatic thiols to acrylic acids followed by the intramolecular Friedel-Crafts acylation of β-arylthiopropanoic acids in the presence of Lewis acid to afford the corresponding products in good yields. This procedure was successfully applied towards the synthesis of the antifungal agent (Z)-3-(4-methoxy benzylidene)-thiochroman-4-one. Chapter two illustrates a method for the synthesis of 3-(1-thio)ethyl-1H-indoles. This simple procedure involves the Michael addition of thiols to 3-indoleacrylic acids and in situ undergo decarboxylation of the Michael adduct by using microwave in DMF at 150 °C.