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標題: 微波加速之有機反應的研究(一)N-芳基鄰胺基苯甲酸衍生物之合成(二)N-取代吡咯-2-羧醛之合成
The Study of Microwave Accelerated Organic Reaction(1) Synthesis of N-Phenylanthranilic Acids(2) Synthesis of N-Substituted Pyrrole-2-carboxaldehyde
作者: 傅凱伶
Fu, Kai-Ling
關鍵字: Microwave
N-Phenylanthranilic Acids
N-Substituted Pyrrole-2-carboxaldehyde
出版社: 化學系所
摘要: 本論文報導我們以微波加速N-芳基鄰胺基苯甲酸以及N-取代吡咯-2-羧醛之合成的研究成果。 一. N-芳基鄰胺基苯甲酸 我們發現在微波照射下,N-芳基鄰胺基苯甲酸的產率和傳統加熱的產率相當,但反應時間可從傳統加熱所需的2~ 4小時降至使用家用微波爐以800 W照射10分鐘,聚焦式微波反應裝置以270 W照射10分鐘。 而當不使用任何溶劑,僅以純反應物來進行反應或利用鹼性固態擔體的反應條件下皆無法得到預期產物,故此反應必須在有溶劑與催化劑存在的條件下才會進行。 二. N-取代吡咯-2-羧醛 我們成功地利用田口實驗設計方法快速地尋找微波加速N-取代吡咯-2-羧醛之合成反應條件,而將傳統加熱所需的4~15小時降至使用聚焦式微波反應裝置以270 W照射20分鐘,且其產率較傳統加熱方式提升2~ 14倍。 因此,我們已成功地建立一個手續簡便的合成N-芳基鄰胺基苯甲酸之方式。以及發展出一個有效利用微波照射加速N-取代吡咯-2-羧醛之合成方法。所以,利用微波照射已經被證實可有效加速有機反應的方法,並且對工業具有很大的應用潛力。
We report herein our studies on microwave-assisted N-phenylanthranilic acids formation and the synthesis of N-substituted pyrrole-2-carboxaldehyde. I. Preparation of N-phenylanthranilic acids The reaction times of the formation of N-phenylanthranilic acids, by reacting o-chlorobenzoic acid and substituted aniline, were greatly reduced from 2~4 hours in conventional method to 10 min by using domestic microwave irradiation at 800 W, and focused microwave irradiation at 270 W, while the yields were comparable. The above reaction did not work under neat or solid support conditions. II. Synthesis N-substituted pyrrole-2-carboxaldehyde Taguchi''s method was employed in the experimental conditions to afford highest yield of N-substituted pyrrole-2-carboxaldehyde utilizing microwave irradiation. We have not only decreased the reaction time from 4~15 hours under conventional heating to only 20 min by focused microwave irradiation at 270 W, but also drastically improved the yields 2~14 times. In conclusion, microwave irradiation has been proved to be an effective method in accelerating organic reactions and therefore has an immense potential in industrial applications.
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