氯化亞銅參與反應製備四氮五環二烯之研究

Study on the synthesis of tetrazole by reaction involving cuprous chloride

陳俊廷(Jun-Ting Chen)

指導教授 ： 楊嘉喜

中原大學/理學院/化學系/碩士(2006年)

https://doi.org/10.6840/cycu200600290

摘要

本研究利用氯化亞銅來活化疊氮官能基進而進行[3+2]環化反應，本實驗環化反應步驟類似於Diels-Alder環化反應，且嘗試不同的反應方式來合成四氮五環二烯基(tetrazolyl)衍生物。而本研究分為A、B兩部分，A部分是利用氯化亞銅與疊氮化鈉相互反應而形成類似疊氮化亞銅之複合物，再與腈基化合物進行[3+2]環化反應而得到產物tetrazole衍生物; B部分則是利用醛類化合物與腈化鈉和醋酸酐來製備腈類化合物再與其疊氮化亞銅複合物進行[3+2]環化反應，由於在實驗處理當中醋酸根會水解成羥基，而我們最後可得到一系列新產物在α位置帶有羥基之tetrazole衍生物，在B部分所形成的產物由於其結構特殊，且並無相關文獻報導，故嘗試去做對於螢光桿狀病毒測試其螢光抑制效果以證實具有藥理活性，觀察tetrazole衍生物相關性質。
由於疊氮化亞銅複合物形式複雜影響本研究合成tetrazolez之產率無法有效提高，鑑於此原因本研究也嘗試著不同金屬與疊氮化鈉發生反應，而且測試實驗溫度的不同對產率的影響等種種思考方向來求證其產率不高之實驗結果; 以及利用亞銅對腈基碳端具有反應性，而以不同反應機制來製備tetrazole，發現以此反應途徑來製備2-H tetrazole。

關鍵字

氯化亞銅 ； 四氮五環二烯

並列摘要

The purpose of this study is to use coprous chloride to activate azide group in [3+2] cycloaddition reaction. Similar to Diels-Alder cycloaddition reaction, we tried to synthesize tetrazole derivatives in different ways. These experiments are divided into A and B parts. In part A, we first used cuprous chloride to react with sodium azide to synthesize an azide-Cu(I) complex. Then, this complex was reacted by nitrile to synthesize tetrazole derivatives in [3+2] cycloaddition reaction. In part B, aldehyde was reacted with sodium cyanide and acetic anhydeide to synthesize α-Acetoxy nitrile, which was later reacted with azide-Cu(I) complex in [3+2] cycloaddition reaction. Acetic group can be hydrolyzed into hydroxyl group in our reaction, so we produced some new tetrazole deriveatives with α-hydroxy group. Due to the special structure of the production in part B, and there were few referential literature, we do the fluorescent of baculovirus test further to observe if it have medicinal activities, and discuss the characteristics of tetrazole derivatives.
Because azide-Cu(I) complex is too complicated, it decrease the efficiency of synthesizing tetrazolez. Hence, we tried different metals and in order to improve the temperature to discuss the cycloaddition. Further, 2-H tetrazole was preperated by the of cyanide and Cu(I) followerd by the addition of sodium cyanide, we tried different mechanism to produce another tetrazole derivatives, 2-H tetrazole.

並列關鍵字

cuprous chloride ； tetrazole

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