應用多組成反應合成色烯類及其他雜環化合物

蔡承軒(Tsai Chen Hsuan)

指導教授 ： 姚清發

國立臺灣師範大學/理學院/化學系/碩士(2009年)

摘要

本實驗以「理想合成(ideal synthesis)」及「綠色化學(green chemistry)」為目標，開發出快速、高產率的合成方法，並結合多組成反應策略(multicomponent strategy)及氟化四丁基銨(Tetrabutylammonium fluoride, TBAF．3H2O)，在水溶液中迴流，合成一系列色烯類衍生物及其他雜環化合物，反應中經過Knoevenagel縮合及環化加成反應兩步驟，其中不需任何純化即可得到最終產物；利用產物不溶水的特性，過濾回收含有氟化四丁基銨的水溶液便可再次催化反應進行，此為本實驗最大的發現與收獲。

關鍵字

四丁基氟化銨 ； 多組成反應 ； 色烯類化合物

並列摘要

The main theme of the dissertation is to study the multicomponent reactions (MCRs). The investigations carried out were divided into four chapters.
The first chapter includes the synthesis of chromene which was obtained by the condensation of an aromatic aldehyde, malononitrile and demidone catalyzed by reusable catalyst TBAF.
The second chapter includes the reaction of aromatic aldehyde, β-napthol and dimidone to afford xanthenone derivative in good yields.
The third chapter describes the synthesis of benzochromene achieved from the MCR of aromatic aldehyde, malononitrile and α- or β-napthol.
The fourth chapter illustrates the synthesis of aromatic aldehyde, malononitrile and α- or β-napthol to the corresponding benzopyranopyridine.
The generality of the above MCRs were studied with a variety of aromatic aldehydes including electron-donating and electron-withdrawing groups and found to be equally good. The use of water as the solvent and also the recyclability of the catalyst (TBAF) employed has the advantages of being economically viable and more efficient for the multicomponent reactions in aqueous media. Overall we can have developed simple and efficient routes for the synthesis of biologically important heterocycles.

並列關鍵字

TBAF ； multicomponent ； chromene

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