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| 研究生： |
邱莉茵 |
|---|---|
| 論文名稱： |
高效率合成含氮、氧、硫雜環化合物之研究 |
| 指導教授： |
姚清發
Yao, Ching-Fa 黃文彰 Huang, Wen-Chang |
| 學位類別： |
碩士 Master |
| 系所名稱： |
化學系 Department of Chemistry |
| 論文出版年： | 2011 |
| 畢業學年度： | 99 |
| 語文別： | 中文 |
| 論文頁數： | 308 |
| 中文關鍵詞： | 水上反應 、麥克加成 、銅(II)催化劑 、雜環分子 |
| 英文關鍵詞： | On Water, Michael addition, copper acetate, heterocyclic compounds |
| 論文種類： | 學術論文 |
| 相關次數： | 點閱：100 下載：5 |
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本論文分為兩部分，第一部分主要探討利用“on water”的方式，使用3-硝基色烯及硫酚經由Michael加成反應路徑而形成C-S鍵，反應時利用可回收的四丁基氟化銨作為催化劑來催化反應，而獲得一系列高產率及高選擇性之3-nitro-2-aryl-4-(arylthio)chroman衍生物。
第二部分主要探討以簡單一鍋化的方式有效的合成N-(3-phenyl-4-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)thiazol-2(3H)-ylidene)benzamide的衍生物，此化合物之結構中含有兩個高生物活性的雜環分子系統，可能具有生物學研究之潛力。同時，製備1,2,3-三唑化合物時，亦可在不使用還原劑的情況下，以銅(II)催化劑做催化進行反應，依然可成功的得到高選擇性之1,4-雙取代的1,2,3-三唑化合物產物。
There are two parts in this dissertation. The first part included “On Water’’ mediated diastereoselective thia-Michael addition of thiophenol to 3-nitrochromene afford 3-nitro-2-aryl-4-(arylthio)chroman in good selectivity and yield at room temperature is described. The assortment of this protocol has been demonstrated by synthesizing an array of 3-nitro-2-aryl-4-(arylthio)chroman derivatives. Easy isolation and simple reaction condition are the important features of the methodology.
The second part included a simple and efficient one-pot synthesis of N-(3-phenyl-4-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)thiazol-2(3H)-ylidene)benza-mide derivatives by using copper acetate as a catalyst. No reducing agent is used in the reaction. The starting can be easily accessed by using known chemistry. Finally, we have demonstrated the synthetic utility of the present procedure by preparing bis triazole compounds.
1. Rideout, D. C.; Breslow, R. J. Am. Chem. Soc. 1980, 102, 7816.
2. Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew. Chem. Int. Ed. 2005, 44, 3275.
3. (a) Guizzetti, S.; Benaglia, M.; Raimondi, L.; Celentano, G. Org. Lett. 2007, 9, 1247; (b) Adib, M.; Mahdavi, M.; Ansari, S.; Malihi, F.; Zhu, L.-G.; Bijanzadeh, H. R. Tetrahedron Lett. 2009, 50, 7246; (c) Ohnmacht, S. A.; Culshaw, A. J.; Greaney, M. F. Org. Lett. 2010, 12, 224; (d) Amantini, D.; Fringuelli, F.; Pizzo, F. J. Org. Chem. 2002, 67, 7238.
4. Woodward, R. B.; Baer, H. J. Am. Chem. Soc. 1948, 70, 1161.
5. Grieco, P. A.; Garner, P.; He, Z.-M.Tetrahedron Lett. 1983, 24, 1897.
6. (a) Grieco, P. A.; Brandes, E. B.; McCann, S.; Clark, J. D. J. Org. Chem. 1989, 54, 5849; (b) McMurry, J. E.; Andrus, A.; Ksander, G. M.; Musser, J. H.; Johnson, M. A. Tetrahedron 1981, 37 (Supplement 1), 319.
7. (a) Venkatraman, S.; Meng, Y.; Li, C.-J.Tetrahedron Lett. 2001, 42, 4459; (b) Shimizu, S.; Shirakawa, S.; Suzuki, T.; Sasaki, Y. Tetrahedron 2001, 57, 6169; (c) Mori, Y.; Kakumoto, K.; Manabe, K.; Kobayashi, S. Tetrahedron Lett. 2000, 41, 3107.
8. Zheng, Z.; Perkins, B. L.; Ni, B. J. Am. Chem. Soc. 2010, 132, 50.
9. (a) Zwanenburg, B.; Klunder, A. J. H. I. Perspectives in Organic Chemistry of Sulfur, Elsevier: Amsterdam, 1987; (b) Cremlyn, R. J., An Introduction to Organosulfur Chemistry; John Wiley & Sons: Chischester, 1996.
10. Fujita, E.; Nagao, Y. Bioorg. Chem. 1977, 6, 287.
11. Trost, B. M.; Keeley, D. E. J. Org. Chem. 1975, 40, 2013.
12. (a) Zhu, S.; Cohen, T. Tetrahedron 1997, 53, 17607; (b) Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417; (c) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043.
13. Cherkauskas, J. P.; Cohen, T. J. Org. Chem. 1992, 57, 6.
14. Kobyashi, S.; Ogawa, C.; Kawamura, M.; Sugiura, M. synlett , 2001, 983.
15. (a) Clark, S. L.; Porter, T. F.; West, F. G. Obstet. Gynecol. 2000, 95, 938; (b) Hirsh, J.; Fuster, V.; Ansell, J.; Halperin, J. L. J. Mol. Struct. 2003, 649, 169.
16. Perkin, W. H. J. Chem. Soc. 1877, 31, 388.
17. Bradford, P. M.; Michael, G. E.; Frank, G.; Favaloro, J. Named Reactions and Reagents in Organic Synthesis, John Wiley &Sons: New York. pp 490.
18. (a) Burrell, G.; Cassidy, F.; Evans, J. M.; Lightowler, D.; Stemp, G. J. Med. Chem. 1990, 33, 3023; (b) Gericke, R.; Harting, J.; Lues, I.; Schittenhelm, C. J. Med. Chem. 1991, 34, 3074.
19. Bowers, W. S.; Ohta, T.; Cleere, J. S.; Marsella, P. A. Science 1976, 193, 542.
20. Virányi, A.; Marth, G.; Dancsó, A.; Blaskó, G.; Toke, L.; Nyerges, M. Tetrahedron 2006, 62, 8720.
21. Habib, P. M.; Rama Raju, B.; Kavala, V.; Kuo, C.-W.; Yao, C.-F. Tetrahedron 2009, 65, 5799.
22. Yousef, G. G.; Grace, M. H.; Cheng, D. M.; Belolipov, I. V.; Raskin, I.; Lila, M. A. Phytochemistry 2006, 67, 2380.
23. (a) Ferreira, D.; Slade, D. Natural Product Reports 2002, 19, 517; (b) Torres, J. L.; Bobet, R. J. Agric. Food Chem. 2001, 49, 4627.
24. Korotaev, V. Y.; Sosnovskikh, V. Y.; Kutyashev, I. B.; Kodess, M. I. Russ.Chem.Bull., Int.Ed. 2006, 55, 317.
25. Hu, Z.-p.; Zhang, J.-m.; Lou, C.-l.; Wang, J.-j.; Nie, S.-z.; Yan, M. ARKIVOC 2010, 17.
26. (a) Mori, A.; Kawashima, J.; Shimada, T.; Suguro, M.; Hirabayashi, K.; Nishihara, Y. Org. Lett. 2000, 2, 2935; (b) Barluenga, J.; Andina, F.; Fernández-Rodríguez, M. A.; García-García, P.; Merino, I.; Aguilar, E. J. Org. Chem. 2004, 69, 7352.
27. David Crouch, R. Tetrahedron 2004, 60, 5833.
28. (a) Capperucci, A.; Degl'Innocenti, A.; Leriverend, C.; Metzner, P. J. Org. Chem. 1996, 61, 7174; (b) Sirol, S.; Courmarcel, J.; Mostefai, N.; Riant, O. Org. Lett. 2001, 3, 4111.
29. (a) Albanese, D.; Landini, D.; Penso, M. J. Org. Chem. 1998, 63, 9587; (b) Shellhamer, D. F.; Horney, M. J.; Pettus, B. J.; Pettus, T. L.; Stringer, J. M.; Heasley, V. L.; Syvret, R. G.; Dobrolsky, J. M. J. Org. Chem. 1999, 64, 1094.
30. (a) Clark, J. H. Chem. Rev. 1980, 80, 429; (b) Ooi, T.; Maruoka,K. Acc. Chem. Res. 2004, 37, 526.
31. Yan, M.-C.; Jang, Y.-J.; Kuo, W.-Y.; Tu, Z.; Shen, K.-H.; Cuo, T.-S.; Ueng, C.-H.; Yao, C.-F.HETEROCYCLES 2002, 57, 1033.
