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| 研究生： |
簡弘聖 Chien, Hung-Sheng |
|---|---|
| 論文名稱： |
碘催化吲哚與4-羰基-2,4-二苯基丁醛苯環化合成咔唑衍生物 Iodine-Catalyzed Benzannulation of Indoles with 4-Oxo-2,4-diphenylbutanals for the Synthesis of Carbazoles Derivatives |
| 指導教授： |
姚清發
Yao, Ching-Fa |
| 口試委員： |
姚清發
Yao, Ching-Fa 林文偉 Lin, Wen-Wei 柳如宗 Liu, Ju-Tsung |
| 口試日期： | 2023/06/28 |
| 學位類別： |
碩士 Master |
| 系所名稱： |
化學系 Department of Chemistry |
| 論文出版年： | 2023 |
| 畢業學年度： | 111 |
| 語文別： | 中文 |
| 論文頁數： | 147 |
| 中文關鍵詞： | 咔唑 、碘 、親電芳香取代反應 、消去反應 、苯環化 |
| 英文關鍵詞： | Carbazole, Iodine, Electrophilic Aromatic substitution, Elimination reaction, Benzannulation |
| 研究方法: | 實驗設計法 |
| DOI URL： | http://doi.org/10.6345/NTNU202301041 |
| 論文種類： | 學術論文 |
| 相關次數： | 點閱：55 下載：3 |
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本篇論文首先回顧了關於咔唑(Carbazole)及其衍生物的合成和應用，接著是報導了我們所開發出的咔唑化合物合成策略以及結論的資訊。我們的合成策略是使用碘當為路易斯酸的催化條件下，將吲哚(Indole)和4-羰基-2,4-二苯基丁醛(4-Oxo-2,4-diphenylbutanal)進行兩次的親電芳香取代(SEAr)反應，反應機構推測會經過幾次的消去反應後並進行苯環化，而成功的合成出咔唑產物。
This thesis reviews the synthesis and application of Carbazole and its derivatives at the beginning, followed by the synthesis strategy and conclusion of Carbazole compounds developed by us. The synthesis strategy we use is to use iodine as the catalytic condition of Lewis acid, indole will undergo two electrophilic aromatic substitution reactions on 4-Oxo-2,4-diphenylbutanal, And, it is speculated that there will be two elimination reactions to achieve Benzannulation, and finally the carbazole product is successfully synthesized.
Zhang, F.-F.; Yan, J.-P.; Zhou, C.-H. Chin. J. Org. Chem. 2010, 30 (6), 783-796.
Smith, Hugh M. (EDT). (2002). High Performance Pigments. U.S.: John Wiley & Sons Inc.
Wu, T.-S.; Huang, S.-C.; Wu, P.-L.; Teng, C.-M. Phytochemistry 1996, 43 (1), 133-140.
Thilahgavani, N.; Perumal, R.; Mohd, E. A. W.; Thirukanthan, C. S.; Charles, S. V. Molecules 2011, 16, 9651-9664.
Drechsel, E. J. Prakt. Chem. 1888, 38 (1), 65-74.
Borsche, W. Justus Liebigs Ann. Chem. 1908, 359 (1-2), 49-80.
Graebe, C.; Ullmann, F. Justus Liebigs Ann. Chem. 1896, 291 (1-2), 16-17.
Tucker, S. H.; Preston, R. W. G.; Cameron, J. M. L. J. Chem. Soc. 1942, 500.
Creencia, E. C., Kosaka, M., Muramatsu, T., Kobayashi, M., Iizuka, T. Horaguchi, T. J. Heterocyclic Chem. 2009, 46 (6), 1309-1317.
Jia, G.-C.; Lin, Z.-Y.; Guo, T.-X.; Li, J.; Shou, W.-G. Organometallics 2009, 28 (24), 6847–6854.
Yamashita, M.; Horiguchi, H.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74 (19), 7481–7488.
Kundu, B.; Saifuddin, M.; Mandadapu, K. A.; Samala, S. J. Org. Chem. 2013, 78 (13), 6769–6774.
Li, Z.-P.; Wang, W.-X.; Lu, S.-L.; Lv, L.-Y., Zheng, X.-J. Organic Letters 2014, 16 (19), 5156-5159.
Ferreira, J. R. M.; Silva, R. N.; Rocha, J.; Silva, A. M. S.; Guieu, S. Synlett. 2020, 31 (6), 632-634.
Xu, B.; Hong, X.-H.; Huang, X.-M.; Xu, S.-G. Org. Lett. 2012, 14 (17), 4614-4617.
Ban, K.; Yamamoto, Y.; Sajiki, H.; Sawama, Y. Org. Biomol. Chem. 2020, 18 (20), 3898-3902.
Chi, Y. R.; Tiwari, B.; Xing, C.; Zhang, J. J. Am. Chem. Soc. 2013, 135 (22), 8113-8116.
