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| 研究生： |
杜懿珊 Duh, Yih-Shan |
|---|---|
| 論文名稱： |
有機催化α,β-不飽和醛及2-羥基苯甲醛苯腙製備四取代1,3,4,5-吡唑化合物 Organocatalytic Synthesis of 1,3,4,5-Tetrasubstituted Pyrazole from α,β-Unsaturated Aldehyde and 2-Hydroxybenzaldehyde Phenylhydrazone |
| 指導教授： |
陳焜銘
Chen, Kwun-Min |
| 學位類別： |
碩士 Master |
| 系所名稱： |
化學系 Department of Chemistry |
| 論文出版年： | 2020 |
| 畢業學年度： | 108 |
| 語文別： | 中文 |
| 論文頁數： | 95 |
| DOI URL： | http://doi.org/10.6345/NTNU202001202 |
| 論文種類： | 學術論文 |
| 相關次數： | 點閱：100 下載：7 |
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本題目為利用有機催化反應，合成四取代1,3,4,5-吡唑化合物。在此反應中，以20 mol% DL-脯胺酸為催化劑，進行巴豆醛及苯腙之 [3+2]-環加成反應，芳香化後得到產物吡唑，產率30-51%。DL-脯胺酸首先活化巴豆醛，生成亞胺離子中間體，與苯腙進行 [3+2]-環化反應，芳香化後，便得到四取代吡唑化合物。
An organocatalytic synthesis of 1,3,4,5-tetrasubstituted pyrazole was described. In this study, 20 mol% DL-proline catalyzed the [3+2] cycloaddition of crotonaldehyde with phenylhydrazone followed by aromatization, leading to the pyrazole formation in moderate yield (30-51%). DL-proline activated crotonaldehyde by in situ generation of imium ion intermediate, so that the [3+2] cyclization with phenylhydrazone and aromatization could proceed.
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