研究生: |
江孟潔 Meng-Jie Jiang |
---|---|
論文名稱: |
1.三氯化鐵輔佐之環化反應:多氫吲哚與雙環[2.2.2]辛-2-烯衍生物的合成 2.金(I)催化3-(3-苯基丙炔胺基)環己-2-烯-1-酮的環化反應:二氫喹啉酮衍生物的合成 1.FeCl3-Promoted Intramolecular Cyclization Reactions:Syntheses of Perhydroindoles and Bicyclo[2.2.2]oct-2-enes 2.Gold(I)-Catalyzed Cycloisomerization Reactions of 3-(3-Phenylpropargylamino)cyclohex-2-en-1-ones : Synthesis of Dihydroquinolinones |
指導教授: |
葉名倉
Yeh, Ming-Chang |
學位類別: |
碩士 Master |
系所名稱: |
化學系 Department of Chemistry |
論文出版年: | 2013 |
畢業學年度: | 101 |
語文別: | 中文 |
論文頁數: | 155 |
中文關鍵詞: | 三氯化鐵 、多氫吲哚衍生物 、雙環[2.2.2]辛烯衍生物 、金 、二氫喹啉酮 |
英文關鍵詞: | FeCl3, multi-hydroindoles, bicyclo[2.2.2]oct-2-ene, gold |
論文種類: | 學術論文 |
相關次數: | 點閱:157 下載:5 |
分享至: |
查詢本校圖書館目錄 查詢臺灣博碩士論文知識加值系統 勘誤回報 |
研究主要分成三個部份,第一個部份是利用三氯化鐵輔佐反式4-(3-
芳香基丙炔(對甲苯磺醯基)胺基)環己-2-烯-1-醇進行環化反應,在室溫、空
氣下進行反應得到氯化多氫吲哚衍生物。第二部分是以三氯化鐵輔佐4-(3-
芳香基丙炔基)環己-2-烯-1-醇行環化反應得到氯化雙環[2.2.2]辛烯衍生物,
此環化反應中,三氯化鐵同時當作路易士酸和氯離子的來源。第三部分利
用金(I)催化3-(3-苯基丙炔胺基)環己-2-烯-1-酮行6-endo-dig 環化反應得到
二氫喹啉酮結構。
There are three parts in this study. The first work is the simple and
efficient FeCl3-promoted cyclization/chlorination of trans 4-(3-arylpropargyl
tosyl-amino)cyclohex-2-en-1-ols. The reaction proceeded at room temperature
in air to afford multi-hydroindoles. Second part of this thesis describes the
synthesis of bicyclo[2.2.2]oct-2-ene from 4-(3-arylpropargyl)cyclohex-2-en-1-
ols using FeCl3. In this reaction, FeCl3 reacts as both Lewis acid and the
chloride source for the cyclization/chlorination. Finally, a method to construct
the dihydroquinolinone skeleton from 3-(3-phenylpropargylamino)cyclohex-
2-en-1-ones by a Au(I)-catalyzed 6-endo-dig cycloisomerization was
developed.
(1) Liu, X.-S.; Jiang, J.; Jiao, X.-Y.; Wu, Y.-E.; Lin, J.-H.; Cai, Y.-M. Cancer
Lett. 2009, 274, 16.
(2) Wildman, W. C.; Bailey, D. T. J. Am. Chem. Soc. 1967, 89, 5514.
(3) Rigby, J. H.; Cavezza, A.; Heeg, M. J. J. Am. Chem. Soc. 1998, 120, 3664.
(4) Martin, S. F.; Davidsen, S. K.; Puckette, T. A. J. Org. Chem. 1987, 52,
1962.
(5) Bastida, J.; Berkov, S.; Torras, L.; Pigni, N. B.; de Andrade, J. P.; Martínez,
V.; Codina, C.; Viladomat, F. Recent Advances in Pharmaceutical Sciences
2011, 65.
(6) Nishimata, T.; Sato, Y.; Mori, M. J. Org. Chem. 2004, 69, 1837.
(7) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106.
(8) Brem, B.; Seger, C.; Pacher, T.; Hofer, O.; Vajrodaya, S.; Greger, H. J.
Agric. Food. Chem. 2002, 50, 6383.
(9) Birch, A.; Grimshaw, J.; Turnbull, J. J. Chem. Soc. (Resumed) 1963, 2412.
(10) Magnus, P.; Gazzard, L.; Hobson, L.; Payne, A. H.; Rainey, T. J.; Westlund,
N.; Lynch, V. Tetrahedron 2002, 58, 3423.
(11) Deutsch, H. M.; Gelbaum, L. T.; McLaughlin, M.; Fleischmann, T. J.;
Earnhart, L. L.; Haugwitz, R. D.; Zalkow, L. H. J. Med. Chem. 1986, 29,
2164.
(12) Spangler, J. E.; Sorensen, E. J. Tetrahedron 2009, 65, 6739.
(13) Bringmann, G.; Reichert, Y.; Kane, V. V. Tetrahedron 2004, 60, 3539.
(14) Ramesh, S.; Nagarajan, R. J. Org. Chem. 2013, 78, 545.
(15) Kantevari, S.; Patpi, S. R.; Addla, D.; Putapatri, S. R.; Sridhar, B.;
Yogeeswari, P.; Sriram, D. ACS Comb. Sci. 2011, 13, 427.
(16) Pearce, A. N.; Chia, E. W.; Berridge, M. V.; Clark, G. R.; Harper, J. L.;
Larsen, L.; Maas, E. W.; Page, M. J.; Perry, N. B.; Webb, V. L. J. Nat. Prod.
2007, 70, 936.
(17) Trost, B. M.; Chen, S. F. J. Am. Chem. Soc. 1986, 108, 6053.
(18) Oppolzer, W.; Gaudin, J.-M.; Bedoya-Zurita, M.; Hueso-Rodriguez, J.;
Raynham, T.; Robyr, C. Tetrahedron Lett. 1988, 29, 4709.
(19) Oppolzer, W.; Bedoya-Zurita, M.; Switzer, C. Y. Tetrahedron lett. 1988, 29,
6433.
(20) Baeckvall, J. E.; Andersson, P. G. J. Am. Chem. Soc. 1990, 112, 3683.
(21) Negishi, E.-i.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett.1986, 27,
2829.
(22) Mori, M.; Uesaka, N.; Saitoh, F.; Shibasaki, M. J. Org. Chem. 1994, 59,
5643.
(23) Hanessian, S.; Tremblay, M. Org. Lett. 2004, 6, 4683.
(24) Lemaire, S.; Giambastiani, G.; Prestat, G.; Poli, G. Eur. J. Org. Chem.
2004, 2840.
(25) Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2005, 127, 6962.
(26) Yeh, M.-C. P.; Pai, H.-F.; Lin, Z.-J.; Lee, B.-R. Tetrahedron 2009, 65,
4789.
(27) Meng, T.-j.; Hu, Y.-m.; Sun, Y.-j.; Zhu, T.; Wang, S. Tetrahedron 2010, 66,
8648.
(28) Yeh, M.-C. P.; Fang, C.-W.; Lin, H.-H. Org. Lett. 2012, 14, 1830.
(29) Marino, J.; Jaén, J. C. Tetrahedron Lett.1983, 24, 441.
(30) Xu, T.; Yu, Z.; Wang, L. Org. Lett. 2009, 11, 2113.
(31) Gay, R. M.; Manarin, F. V.; Schneider, C. C.; Barancelli, D. A.; Costa, M.
D.; Zeni, G. J. Org. Chem. 2010, 75, 5701.
(32)Wang, Z.; Li, S.; Yu, B.; Wu, H.; Wang, Y.; Sun, X. J. Org. Chem. 2012, 77,
8615.
(33) Cheng, J.; Tang, X.; Ma, S. ACS Catal. 2013, 3, 663.
(34) Wang, S.; Zhang, L. J. Am. Chem. Soc. 2006, 128, 14274.
(35) Reeds,J. P.; Whitwood, A. C.; Healy, M. P.; Fairlamb, I. J. Organometallics
2013, 32, 3108.
(36) Yeh, M.-C. P.; Pai, H.-F.; Hsiow, C.-Y.; Wang, Y.-R. Organometallics 2009,
29, 160.
(37) Brummond, K. M.; Chen, D. Org. Lett. 2008, 10, 705.
(38) Conrad, R. M.; Du Bois, J. Org. Lett. 2007, 9, 5465.
(39) Ceylan, M.; Findik, E. Synth. Commun. 2008, 38, 2584.
(40) Fíndík, E.; Ceylan, M.; Elmastaş, M. J. Heterocycl. Chem. 2012, 49, 253.
(41) Srinivas, K.; Dinesh, A.; Balasubramanian, S. Synthesis 2010, 3745.
(42) Zhong, W.; Lin, F.; Chen, R. E.; Su, W. Synthesis 2008, 2561.
(43) Abbiati, G.; Arcadi, A.; Bianchi, G.; Di Giuseppe, S.; Marinelli, F.; Rossi,
E. J. Org. Chem. 2003, 68, 6959.
(44) Cacchi, S.; Fabrizi, G.; Filisti, E. Org. Lett. 2008, 10, 2629.
(45) Saito, A.; Konishi, T.; Hanzawa, Y. Org. Lett. 2010, 12, 372.
(46) Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 15978.
(47) Xiao, Y. P.; Liu, X. Y.; Che, C. M. Angew. Chem. Int. Ed. 2011, 50, 4937
(48) Brazeau, J.-F. o.; Zhang, S.; Colomer, I.; Corkey, B. K.; Toste, F. D. J. Am.
Chem. Soc. 2012, 134, 2742.
(49) Watanabe, T.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2007, 9, 4821.
(50) Mauleón, P.; Zeldin, R. M.; González, A. Z.; Toste, F. D. J. Am. Chem. Soc.
2009, 131, 6348.
(51) Huang, X.; Zhang, L. J. Am. Chem. Soc. 2007, 129, 6398.
(52) Huang, X.; Zhang, L. Org. Lett. 2007, 9, 4627.
(53) Winkler, J. D.; Ragains, J. R. Org. Lett. 2006, 8, 4031.
(54)T Putkonen, A Tolvanen, R Jokela, S Caccamese, N Parrinello Tetrahedron
2003, 59, 8589.
(55) Jiang, C.; Xu, M.; Wang, S.; Wang, H.; Yao, Z.-J. J. Org. Chem. 2010, 75,
4323.
(56) Fei, N.; Yin, H.; Wang, S.; Wang, H.; Yao, Z.-J. Org. Lett. 2011, 13, 4208.
(57) Yin, H.; Kong, F.; Wang, S.; Yao, Z.-J. Tetrahedron Lett.2012, 53, 7078.