研究生: |
方顥伶 |
---|---|
論文名稱: |
利用碘催化以及一鍋式方法合成具有生物活性的十氫喹啉及黃烷酮衍生物 One-Pot Synthesis of Bioactive Decahydroquinolines and Flavanone Derivatives Using Iodine as Catalyst |
指導教授: | 姚清發 |
學位類別: |
碩士 Master |
系所名稱: |
化學系 Department of Chemistry |
論文出版年: | 2007 |
畢業學年度: | 95 |
語文別: | 中文 |
論文頁數: | 204 |
中文關鍵詞: | 十氫喹啉衍生物 、黃烷酮衍生物 |
論文種類: | 學術論文 |
相關次數: | 點閱:189 下載:0 |
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在室溫下,利用碘(iodine)催化醛、苯胺和acetylcyclohenxene以具有選擇性的特性,一鍋合成trans-endo-decahydroquinolin-4-one;此方法具有易操作、反應時間短、高產率、單一產物以及溫和的反應條件的優點。及利用碘(iodine)催化醛和2-hydroxyacetophenone一鍋合成黃烷酮衍生物,此方法具有易操作、高產率、單一產物以及適用於各種官能基的優點。
第一部份
參考文獻
1.(a) Viera, E.; Binggeli, A.; Brue, V. Bur, D; Fischli, W. Guller, R. Hirth, G.; Marki, H. P.; Muller. M.; Oefner. C. Stadler, H.; Wilhelm, M.; Wostl, W. Bioorg. Med. Chem. Lett. 1999, 9, 1379;(b) Guller, R. Binggeli, A.; Breu, V.; Bur, D.; Fischli, W.; Hirth, G.; Jenny, C.; Kansy, M.; Montavon, F.; Muller, M.; Oefner. C.; Stadler, H.; Vieira, E.; Wilhelm, M.; Wostl, W.; Marki, P. Bioorg. Med. Chem. Lett. 1999, 9, 1403.
2.Khadem, S; Joseph, R; Rastegar, M; Leek, D; Qudatchin, K; Arya, P; J. Comb. Chem. 2004, 6, 724-734
3. (a) Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 3559. (b) Bromidge, S.; Wilson, P. C.; Whiting, H. Tetrahedron Lett. 1998, 39, 8905. (c) Jorgensen, K. A.; Hazell, R. G.; Audrain, H.; Johansen, M.; Yao, S. J. Am. Chem. Soc. 1998, 120, 8599. (d) Kobayashi, S.; Kusakabe, K.-I.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220.
4. Ishimaru. K; Yamamoto, Y; Akiba, K; Tetrahedron 1997, 53, 423-5432
5. Kobayashi, S.; Komiyama, S.; Ishitani, H. Angew. Chem., Int. Ed. 1998, 37, 979.
6. Le Coz, L.; Veyrat-Martin, C.; Wartsky, L.; Seyden-Penne, J.; Bois, C.; Philoche-Levisalles, M. J. Org. Chem. 1990, 55, 4870.
7. Paugam, R.; Valenciennes, E.; Coz-Bardol, L. L.; Garde, J-C.; Wartski, L.; Lance, M.; Nierlich, M. Tetrahedron Asymm. 2000, 11, 2509.
8. (a) Nogue , D.; Paugam, R.; Wartski, L. Tetrahedron Lett. 1992, 33, 1265. (b) Paugam, R.; Wartski, L. Tetrahedron Lett. 1991, 32, 491.
9. (a) Kim, K. M.; Ryu, E. K. Tetrahedron Lett. 1996, 37, 1441. (b) Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. J. Org. Chem. 2001, 66, 7527. (c) Firouzabadi, H.; Iranpoor, N.; Sobhani, S. Tetrahedron Lett. 2002, 43, 3653. (d) Bandgar, B. P.; Shaikh, K. A. Tetrahedron Lett. 2003, 44, 1959. (e) Saeeng, R.; Sirion, U.; Sahakitpichan, P.; Isobe, M. Tetrahedron Lett. 2003, 44, 6211. (f) Phukan, P. J. Org. Chem. 2004, 69, 4005.
10. Sun, J.; Dong, Y; Wang, X.; Wang, S.; Hu, Y. J. Org. Chem. 2004, 69, 8932.
11. Lin, C.; Hsu, J.; Sastry, M. N. V.; Fang, H.; Tu, Z.; Liu, J.-T.; Yao, C.-F. Tetrahedron 2005, 61, 11751.
12. Monnereau, C.; Blart, E.; Odobel, F. Tetrahedron 2005, 46, 5421.
13. Babu, G.; Perumal, P. T. Tetrahedron 1998, 54, 1627.
第二部份
參考文獻
1.(a) Ferrali, M.; Donati, D.; Bambagioni, S.; Fontani, M.; Giorgi, G.; Pietrangelo, A. Bioorg. Med. Chem. 2001, 9, 3041; (b) Lipinski, C. A.; Aldinger, C. E.; Beyer, T. A.; Bordner, J.; Burdi, D. F.; Bussolotti, D. L.; Inskeep, P. B.; Siegel, T. W. J. Med, Chem. 1992, 35, 2169; (c) Pouget, C.; Fagnere, C.; Basly, J-P.; Habrioux, G.; Chulia, A-J. Bioorg.Med. Chem.Lett. 2002, 12, 1059– 1061.
2.van Acker, F. A. A.; Hageman, J. A.; Haenen, G. R. M. M.; van der Vijgh, W. J. F.; Bast, A.; Menge, W. M. P. B. J. Med. Chem. 2000, 43, 3752.
3.Nussbaumer, P.; Lehr, P.; Billich, A. J. Med. Chem. 2002, 45, 4310
4.Brennan, C. M.; Hunt, I.; Jarvis, T. C.; Johnson, C. D.; McDonnell, P. D. Can. J. Chem. 1990, 68, 1780
5.(a) Thomsen, I.; Torssell, B. G. Acta Chem. Scand. Ser. B 1988, 42, 303; (b) Climent, M. J.; Garcia, H.; Iborra, S.; Miranda, M. A.; Primo, J. Hetrocycles 1989, 29, 115 ; (c) Chandrasekhar, S. ; Vijeender, K.; Reddy, K. V. Tetrahedron Lett. 2005, 46, 6991.
6.(a) Stermitz, F. R.; Adamovics, J. A.; Geigert, J. Tetrahedron 1975, 31, 1593; (b) Pandey, G.; Krishna, A.; Kumaraswamy, G. Tetrahedron Lett. 1987, 28, 4615;
7.Sanicanin, Z.; Tabakovic, I. Tetrahedron Lett. 1986, 27, 407
8.Chandrasekhar, S.; Vijeender, K.; Reddy, K. V. Tetrahedron Lett. 2005, 46, 6991
9.Choudary, B. M.; Ranganath, K. V. S.; Yadav, J.; Kantam, M. L. Tetrahedron Lett. 2005, 46, 1369
10.Hoshino, Y.; Takeno, N. Bull. Chem. Soc. Jpn. 1986, 59, 2903
11.Synlett 2006, 14, 2159-2175
12.Kitagawa, O; Hanano, T; Kikuchi, N; Taguchi, T; Tetrahedron Lett. 1993, 34, 2165
13.Pedra, M.S.C; Tha, M. J. Org. Chem. 2005, 70, 1828
14.(a) Chu, C.-M.; Gao, S.; Sastry, M. N. V.; Yao, C.-F. Tetrahedron Lett, 2005, 46, 4971. (b) Ko, S.; Sastry, M. N. V.; Lin, C.; Yao, C.-F. Tetrahedron Lett, 2005, 46, 5771. (c) Shivaji, V. M.; Sastry, M. N. V.; Wang, C.-C.; Yao, C.-F. Tetrahedron Lett. 2005, 46, 6345. (d) Lin, C.; Hsu, J.; Sastry, M. N. V.; Fang, H.; Tu, Z.; Liu, J.-T.; Yao, C.-F. Tetrahedron 2005, 61, 11751. (e) Ko, S.; Lin, C.; Tu, Zhijay,; Wang, Y.-F.; Wang, C.-C.; Yao, C.-F. Tetrahedron Lett. 2006, 47, 487. (f) Gao, S.; Tzeng, T.; Sastry, M. N. V.; Chu, C.-M.; Liu, J.-T.; Lin, C.; Yao, C.-F. Tetrahedron Lett. 2006, 47, 1889.