胺與氯烯酮反應合成 α-氯烯胺酮的原子經濟策略

Abstract

由於烯胺酮已被廣泛用於製備各種雜環、有機分子和生物學上重要的分子。因此，在有機合成領域中，它非常有吸引力。本論文敘述 (Z)-2-氯-1-苯基-3-(苯氨基)-2-丙烯-1-酮的合成。首先介紹關於烯胺酮衍生物的藥理重要性及合成烯胺酮的文獻回顧。從文獻回顧中發現用二甲基亞碸 (DMSO) 作為溶劑、試劑和氧化劑有廣泛的應用。因此我們嘗試用毒性低、便宜和綠色化學的二甲基亞碸作為綠色氧化劑，經由氧化和氯化反應以原子經濟的方式來生成 α-氯烯胺酮。反應路徑推測是經由胺與氯烯酮進行邁克爾加成反應 (Michael addition) 後，再除去鹽酸得到烯胺酮。Enaminones are very attractive in organic synthesis due to their wide applicability to the preparation of various heterocycles, organic molecules and biologically important molecules. This thesis describes the synthesis of (Z)-2-chloro-1-phenyl-3-(phenylamino)prop-2-en-1-one.Firstly, the pharmacological importance of enaminone derivatives and literature review on the synthesis of enaminone are introduced.Firstly , the Michael addition of amines to chloroenones gives the enaminones by elimination of hydrochloric acid (HCl). The in-situ oxidation and chloroination generate the α-chloroenaminones in an atom-economical manner using dimethylsulfoxide (DMSO) as a green oxidant.