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Title: 高效率合成三唑化合物的方法及4',6'-二苯基-2'-羥基苯乙酮之合成
Efficient methodologies for the synthesis of 1,2,3-triazoles and 4',6'-diaryl-2'-hydroxyacetophenones
Authors: 姚清發
Yao, Ching-Fa
Kuo, Chia-Ming
Keywords: 三唑
Issue Date: 2013
Abstract: 化學家常可從自然界的動物或植物中分離出許多具有生物活性的天然物。一般而言,此類天然物常具有某些特定的架構,例如吲哚、黃酮、查耳酮、色烯或三唑化合物等。 本論文分為兩個部分,第一部分主要探討以二價的醋酸銅(Cu(OAc)2)作為催化劑。反應過程中可利用CTAB (Cetyltrimethyl- ammonium bromide)來促進格拉澤偶聯反應(Glaser coupling)的進行,藉由反應系統中的部分試劑因進行炔烴的偶合反應,使得二價的銅離子(Cu2+)還原成一價的銅離子(Cu+);同時CTAB亦可用來穩定一價的銅離子(Cu+),進而促使[3+2]環化加成反應的發生。一般而言,此類型反應幾乎是同時得到1,4-雙取代及1,5-雙取代的產物,但本反應最終只得到高產率及高選擇性的1,4-雙取代的1,2,3-三唑化合物產物。 第二部分在設計一個簡單且容易操作的一鍋化反應,在使用DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene)為鹼的條件下,利用二苯基丙炔酮與2,4-戊二酮為反應試劑,首先經由1,4-加成反應;之後,再進行分子內合環、脫水等反應,最終生成4',6'-雙苯基-2'-羥基苯乙酮。此類產物常被化學家用來作為合成天然物的前驅物,其特色為眾多的步驟中,應用此試劑的反應,常是屬於關鍵步驟的反應。 關鍵字:三唑、苯乙酮
This thesis covers the combination of two separate work accomplished during the throughout the study. Among them, the first work deals with a solvent free copper (II) catalyzed azide alkynes cycloaddition reaction. In this project, we achieved a new procedure for azide alkyne cycloaddition reaction in the presence copper acetate and CTAB. Using this procedure, a variety of non chelating azide converted into different structurally diverse triazole derivatives by the reaction with various alkynes. This procedure is equally efficient for the synthesis of bis and tris trialzoles as well. Number functional groups were well tolerated under the described reaction conditions. Easy handling, the use of copper(II) catalyst in absence of reducing agents, rapid and clean reactions, and easy isolation of the products are important features of this method. Second part of the thesis describes a one pot synthesis 2-hydroxy acetophenones from the reaction of 1,3-disubstitutedprop-2-yn-1-one and 1,3-diketones in presence of DBU. This reaction involves Michael addition of 1,3-diketones followed by aldol condensation. This method was applied for the synthesis of different diarylasubstituted hydroxyacetophones in good to moderate yields. Further, similar reaction ketoester and 2-Acetylbutyrolactone provided different compounds. Mechanistic routes for the formation of all the products were rationalized through experimental evidence. Keywords:triazoles、acetophenones
Other Identifiers: GN060042070S
Appears in Collections:學位論文

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