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Title: 氧-取代的醯胺肟環加成反應的研究
Investigation of Cycloaddition Reaction of O-Substituted Amide Oxime
Authors: 簡敦誠
Chien, Tun-Cheng
Chen, Ying-Cheng
Keywords: 環化反應
O-substituted amide oxime
Issue Date: 2017
Abstract: 本研究希望以amide oxime作為起始物進行環化反應來得到含氮雜環分子,研究初期希望以amide oxime與ethyl propiolate進行[3+2]環化加成反應得到五元環含氮雜環,卻意外的發現得到[3+3]環化加成產物2-phenylpyrimidin-4-one,但同時也發現,副反應ethyl propiolate進行[2+2+2]環化加成的反應速率大於[3+3]環化反應的速率,導致研究無法繼續下去。在篩選各種dipolarophic等同物後,發現使用enaminones化合物代替ethyl propiolate得到[3 + 2]環化產物imidazoles衍生物。接著進行後續反應條件優化探討,發現以O-substituteds amide oxime作為起始物與enaminones化合物在催化當量的鐵試劑條件下,成功合成出各種不同取代的imidazoles衍生物。 關鍵字:環化反應,含氮雜環,鐵試劑。
In this study, we used amide oxime as a starting material for cyclization reaction to obtain nitrogen-containing heterocyclic molecules. In the beginning of the study, we anticipated that the amide oxime and ethyl propiolate could undergo [3+2] cycloaddition to afford the five-membered ring nitrogen-containing heterocycls. However, we found that the reaction rate of the side reaction, [2+2+2] cycloaddition of ethyl propiolate to triethyl 1,3,5-benzenetricarboxylate, is greater than the rate of heterocycle formation, which surprisingly formed the six-membered heterocycle, 2-phenylpyrimidin-4-one, instead. After screening of various dipolarophile equivalents, we found that the use of the enaminones compound instead of ethyl propiolate gave the [3+2] cyclized product, and the cyclization adduct was found to be imidazole derivatives After the successful cyclization reaction, the subsequent optimization conditions were discussed. Finally, we found that using O-substituted amide oxime as the starting material reacted with enaminones in the catalytic amount of iron reagent can undergo [3+2] cycloaddition which successfully formed a variety of different substituted imidazole derivatives. Keywords : O-substituted amide oxime, cycloaddition, enaminones, imidazole.
Other Identifiers: G060442082S
Appears in Collections:學位論文

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