壹、經由N-溴代丁二醯亞胺的催化進行Michael addition反應合成具有生物活性分子之前驅物 貳、無催化劑的條件下鄰苯二胺與1,2-二羰基化合物進行縮合脫水反應
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2009
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Abstract
本論文的第壹部分討論使用便宜、容易取得的市售試劑N-溴代丁二醯亞胺(N-bromosuccinimide)來催化共軛硝基乙烯(nitrostyrene)與吲哚(indole)的Michael addition反應，產物為具有生物活性分子之前驅物。此外，我們也使用二烯酮(dienone)與吲哚(indole)在N-溴代丁二醯亞胺(N-bromosuccinimide)的催化下，進行Michael addition反應，其最終產物為雜環的七環化合物。
本論文第貳部分報導一個簡易、快速、高產率的方法，來製備具有生物活性骨架的化合物。如果使用甲醇當作溶劑，在室溫的狀況下，鄰苯二胺(o-phenylenediamine)可與1,2-二羰基化合物(1,2-dicarbonyl compounds)進行縮合脫水反應。除了可當作一般的化學研究用途外，此類產物亦可作為具有發光特性的材料，大大地增加此產物的應用性。
The thesis work of the present finding is divided in to two chapters. The first chapter deals with the C-alkylation of indoles with nitroalkenes in the presence of a cheap and commercial available N-bromosuccinimide as a catalyst. The generality of this method is demonstrated by synthesizing an array of diverse 3-substituted indole derivatives by the reaction of β-nitrostyrenes with various indoles and vice versa. Simple reaction conditions accompanied by good yields of indolyl-nitroalkanes are the merits of this methodology. The second part of this thesis described the synthesis of quinoxiline derivatives which includes a catalyst free condensation of o-phenylenediamine with 1,2-dicarbonyl compounds in methanol at room temperature. This method is simple, quicker and produce high yield of the products. The applicability of the present methodology is further extended by performing the reaction with a wide variety of o-phenylenediamines and 1,2-dicarbonyl compounds to produce corresponding quinoxaline derivatives in excellent yield.
The thesis work of the present finding is divided in to two chapters. The first chapter deals with the C-alkylation of indoles with nitroalkenes in the presence of a cheap and commercial available N-bromosuccinimide as a catalyst. The generality of this method is demonstrated by synthesizing an array of diverse 3-substituted indole derivatives by the reaction of β-nitrostyrenes with various indoles and vice versa. Simple reaction conditions accompanied by good yields of indolyl-nitroalkanes are the merits of this methodology. The second part of this thesis described the synthesis of quinoxiline derivatives which includes a catalyst free condensation of o-phenylenediamine with 1,2-dicarbonyl compounds in methanol at room temperature. This method is simple, quicker and produce high yield of the products. The applicability of the present methodology is further extended by performing the reaction with a wide variety of o-phenylenediamines and 1,2-dicarbonyl compounds to produce corresponding quinoxaline derivatives in excellent yield.
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Keywords
N-溴代丁二醯亞胺, 縮合脫水反應, 生物活性分子