論文使用權限 Thesis access permission：校內外都一年後公開 withheld
開放時間 Available：
校內 Campus： 已公開 available
校外 Off-campus： 已公開 available
博碩士論文 etd-1007104-154659 詳細資訊
Title page for etd-1007104-154659
論文名稱 Title |
第一篇 環戊亞醯胺應用在 1.The Application of Glutarimides in the Synthesis of Piperidine and Isoquinolone Derivatives 2.Regioselective Nucleophilic Addition of Glutarimides and the Applications to the Synthesis of Alkaloids 3.A New Approach to (E)-3-Substituted-N-Alkylacryl-amides and 3,4-Disubstituted Succinimides |
||
系所名稱 Department |
|||
畢業學年期 Year, semester |
語文別 Language |
||
學位類別 Degree |
頁數 Number of pages |
222 |
|
研究生 Author |
|||
指導教授 Advisor |
|||
召集委員 Convenor |
|||
口試委員 Advisory Committee |
|||
口試日期 Date of Exam |
2004-09-27 |
繳交日期 Date of Submission |
2004-10-07 |
關鍵字 Keywords |
3-、[3+3]環合反應、異、親核性加成反應 nucleophilic addition, isoquinoline, 3-piperidinol, [3+3] annulation |
||
統計 Statistics |
本論文已被瀏覽 5671 次，被下載 678 次 The thesis/dissertation has been browsed 5671 times, has been downloaded 678 times. |
中文摘要 |
1.利用[3+3]環合反應以建構環戊亞醯胺的骨架，在選擇性還原後進行取代反應，並應用於天然物及藥物的合成上。 2.利用[3+3]環合反應以建構環戊亞醯胺的骨架，在近行位置選擇性親合基加成反應後，應用於天然物及藥物的合成上。 3.利用alha-磺酸基醯胺在不同的鹼性條件下與鹵烷進行取代以及脫去反應後可得到具共軛雙鍵的化合物，或近行環化反應就可合成出各種不對稱的3,4-雙取代琥珀醯胺。 |
Abstract |
1. A new route towards the synthesis of drugs and alkaloids by using N-alkylsulfonylacetamide and unsaturated ester as starting materials via stepwise [3+3] annulation. 2. The application of regioselective nucleophilic addition of glutarimide which prepared via stepwise [3+3] annulation. 3. Synthesis of (E)-3-Substituted-N-Alkylacryl-amides and 3,4-Disubstituted Succinimides by using N-alkylsulfonyl-acetamide and alkyl halides as starting materials in the different reaction condition. |
目次 Table of Contents |
前言：……………………………………………1 第一篇：環戊亞醯胺應用在 |
參考文獻 References |
1.(a) Strunz, G. M.; Findlay, J. A. The Alkaloids; Academic Press: New York, 1985, Vol. 26.89. (b) Southon, I. W.; Buckingham, J. Dictionary of Alkaloids; Chapman and Hall: London, 1989. (b) Daly, J. W. J. Nat. Prod. 1998, 61, 162. 2.(a) Sugimoto, H.; Tsuchiya, Y.; Sugumi, H.; Higurashi, K.; Karibe, N.; Iimura, Y.; Sasai, A.; Kawakami, Y.; Nakamura, T.; Araki, S.; Yamanishi, Y.; Yamatsu, K. J. Med. Chem. 1990, 33, 1880. (b) Sugimoto, H.; Tsuchiya, Y.; Sugumi, H.; Higurashi, K.; Karibe, N.; Iimura, Y.; Sasaki, A.; Araki, S.; Yamanishi, Y.; Yamatsu, K. J. Med. Chem. 1992, 35, 4542. (c) Sugimoto, H.; Iimura, Y.; Yamanishi, Y.; Yamatsu, K. J. Med. Chem. 1995, 38, 4821. 3.Chen, Y. L. EP441517 A2; Chem Abstr. 1991, 115, 232222. 4.Sugimoto, H.; Tsuchiya, Y.; Higurashi, K.; Karibe, N.; Iimura, Y.; Sasaki, A.; Yamanishi, Y.; Ogura, H.; Araki, S. EP 296560 A2 Chem. Abstr. 1989, 110, 173102. 5.Abe, T.; Haga, T.; Negi, S.; Morita, Y.; Takayanagi, K.; Hamamura, K. Tetrahedron 2001, 57, 2701. 6.(a) Krogsgaard-Larsen, P.; Falch, E. J. Med. Chem. 1981, 24, 285. (b) Cambell, A. L.; Pilipauskas, D. R.; Khanna, I. K.; Rhodes, R. A. Tetrahedron Lett. 1987, 28, 2331. (c) Rohr, M.; Chayer, S.; Garrido, F.; Mann, A.; Taddei, M.; Wermuth, C.-G. Heterocycles. 1996, 43, 2131. 7.(a) Krogsgaard-Larsen, P.; Johnstone, G. A. R.; Lodge, D.; Curtis, D. R. Nature 1977, 268, 53. (b) Krogsgaard-Larsen, P.; Hjeds, H.; Curtis, D. R.; Lodge, D.; Johnston, G. A. R. J. Neurochem. 1979, 32, 1717. (c) Barnard, E. A.; Skolnick, P.; Olsen, R. W.; Mohler, H.; Sieghart, W.; Biggio, G.; Braestrup, C.; Bateson, A. N.; Langer, S. Z. Pharmacol. Reviews 1998, 50, 291. 8.Rohr, M.; Chayer, S.; Garrido, F.; Mann, A.; Taddei, M.; Wermuth, C. G. Heterocycles, 1996, 43, 2131. 9.Kehle, J.; Ebert, B.; Dahl, O.; Krogsgaard-Larsen, P. J. Chem. Soc., Perkin Trans. 1, 1998, 3241. 10. (a) Chang, M. Y.; Chang, B. R.; Tai, H. M.; Chang, N. C. Tetrahedron Lett. 2000, 41, 10273.(b)Huang, C. G.; Chang, B. R.; Chang, N. C. Tetrahedron Lett. 2002, 43, 2721. (c) Chang, B. R.; Chen, C. Y.; Chang, N. C. Tetrahedron Lett. 2002, 43, 3233. (d) Chang, M. Y.; Chen, S. T.; Chang, N. C. Tetrahedron 2002, 58, 3623. (e) Chang, M. Y.; Chen, S. T.; Chang, N. C. Tetrahedron 2002, 58, 5075. (f) Hsu, R. T.; Cheng, L. M.; Chang, N. C.; Tai, H. M. J. Org. Chem. 2002, 67, 5044. (g) Chang, M. Y.; Chen, S. T.; Chang, N. C. Heterocycles 2002, 57, 2321. (h) Lin, C. H.; Tsai, M. R.; Wang, Y. S.; Chang, N. C. J. Org. Chem. 2003 68, 5688. (i) Chang, M. Y.; Chen, S. T.; Chang, N. C. Heterocycles 2003, 60, 99. (j) Chang, M. Y.; Chen, S. T.; Chang, N. C. Synth. Commun. 2003, 33, 1375. 11.Bonjoch, J.; Ferandez, J.-C.; Valls, N. J. Org. Chem. 1998, 63, 7338. 12. Tsai, M. R.; Sun P. P.; Chang, M. Y.; Chang, N. C. J.Chin. Chem. Soc. 2004. 51, 613. 1.(a) Croisy-Delcey, M.; Croisy, A.; Carrez, D.; Huel, C.; Chiaroni, A.; Ducrot, P.; Bisagni, E.; Jin, L.; Leclercq, G. Bioorg. Med. Chem. 2000, 8, 2629. (b) Sulkowski, T. S.; Wille, M. A. U. S. Patent 1969, 3452027, American Home Products Corp.; C. A. 1969, 71,112830. (c) Coyne, W. E.; Cusic, J. W. U. S. Patent 1971, 3600394, Searle & Co.; C. A.1971, 75, 118241. (d) Kubo, K.; Ito, N.; Sozu, I.; Isomura, Y.; Homma, H. Japan Kokai Tokkyo Koho 1979, 79, 163585; C.A. 1980, 93, 8037; Japan Kokai Tokkyo Koho 1979, 79, 92997; C. A. 1980, 92, 111036; Ger. Offen. 1979, 2828528; C. A. 1979, 90, 168468. (e) Wakabayashi, T.; Watanabe, K. Japan Kokai Tokkyo Koho 1978, 78, 119879; C. A. 1979, 90, 152028. (f) Matsui, T.; Sugiura, T.; Nakui, H.; Iguch, S.; Shigeoka, S.; Tukedu, H.; Odagaki, T.; Ushio, Y.; Ohmoto, K.; Iwamani, M.; Yamazaki, S.; Arai, T.; Kawamura, M. J. Med. Chem. 1992, 35, 3307. (g) Li, S. W.; Nair, M. G.; Edwards, D. M.; Kisluick, R. L.; Gaument, Y.; Dev, I. K.; Duch, D. S.; Humphreys, J.; Smith, G. K.; Ferone, R. J. Med. Chem. 1991, 34, 2746. (h) Jones, T. R.; Calvert, A. M.; Jackman, A. L.; Brown, S.; Jones, M.; Harrap, K. R. Eur. J. Cancer 1981, 17,11. 2.Whaley, W. M.; Govindachari, T. R. In Organic Reactions; Adams, R., Ed.; Wiley: New York, 1951; Vol. 6, PP 151-190. 3.Whaley, W. M.; Govindachari, T. R. In Organic Reactions; Adams, R., Ed.; Wiley: New York, 1951; Vol. 6, PP 74-150. 4.Gensler, W. J. In Organic Reactions; Adams, R., Ed.; Wiley: New York, 1951; Vol. 6, PP 191-206. 5.Briet, N.; Brookes, M. H.; Davenport, R. J.; Galvin, F. C. A.; Gilbert, P. J.; Mack, S. R.; Sabin, V. Tetrahedron 2002, 58, 5761. 6.Wu, M. J.; Chang, L. J.; Wei, L. M.; Lin, C. F. Tetrahedron 1999, 55, 13193. 7.(a) Cheng, C. Y.; Chang, B. R.;Tsai, M. R.;Chang. N. C. Tetrahedron 2003. 59. 9383. (b) Hsu, R. T.; Cheng, L. M.; Chang, N. C.; Tai, H. M. J. Org. Chem. 2002, 67, 5044. 8. Tsai, M. R.; Hung, T. C.; Chen, B. F.; Cheng, C. C.; and Chang, N. C. Tetrahedron 2004 in press. 1.Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817. 2.(a) Kraus, G. A.; Neuenschwander, K. J. Chem. Soc., Chem. Commun.1982, 134-135. (b) Thaning, M.; Wistrand, L.-G. HelV. Chim. Acta 1986, 69, 1711. (c) Thaning, M.; Wistrand, L.-G. J. Org. Chem. 1990, 55, 1406. (d) Renaud, P.; Seebach, D. HelV. Chim. Acta 1986, 69, 1704. (e) Arai, Y.; Fujii, A.; Ohno, T.; Koizumi, T. Chem. Pharm. Bull. 1992, 40, 1670. 3.(a) Kano, S.; Yuasa, Y.; Yokomatsu, T.; Shibuya, S. J. Org. Chem.1988, 53, 3865. (b) Onoue, H.; Narisada, M.; Uyeo, S.; Matsumura,H.; Okada, K.; Yano, T.; Nagata, W. Tetrahedron Lett. 1979, 3867. c) Kise, N.; Yamazaki, H.; Mabuchi, T.; Shono, T. Tetrahedron Lett. 1994,35, 1561. (d) Yamada, J.; Satoˆ, H.; Yamamoto, Y. Tetrahedron Lett. 1989, 30, 5611. (e) Ludwig, C.; Wistrand, L.-G. Acta Chem. Scand. 1990, 44, 707. (f) Wistrand, L.-G.; Skrinjar, M. Tetrahedron 1991, 47, 573. (g) Collado, I.; Ezquerra, J.; Pedregal, C. J. Org. Chem. 1995, 60, 5011. (h) Comins, D. L.; Foley, M. A. Tetrahedron Lett. 1988, 29, 6711. (i) Brown, D. S.; Charreau, P.; Hansson, T.; Ley, S. V. Tetrahedron 1991, 47, 1311. (j) Shono, T.; Terauchi, J.; Ohki, Y.; Matsumura, Y. Tetrahedron Lett. 1990, 31, 6385. (k) Hanson, G. J.; Russell, M. A. Tetrahedron Lett. 1989, 30, 5751. 4.(a) Lundkvist, J. R. M.; Wistrand, L.-G.; Hacksell, U. Tetrahedron Lett. 1990, 31, 719. (b) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 1997, 119, 3409. 5.(a) Thaning, M.; Wistrand, L.-G. Acta Chem. Scand. 1989, 43, 290. (b) Katoh, T.; Nagata, Y.; Kobayashi, Y.; Arai, K.; Minami, J.; Terashima, S. Tetrahedron 1994, 50, 6221. (c) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633. 6.(a) Shono, T.; Matsumura, Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172. (b) Shono, T.; Matsumura, Y.; Uchida, K.; Tsubata, K.; Makino, A. J. Org. Chem. 1984, 49, 300. (c) Pilli, R. A.; Russowsky, D. J. Or g. Chem. 1996, 61, 3187. 7.(a) Shono, T.; Matsumura, Y.; Tsubata, K.; Takata, J. Chem. Lett. 1981, 1121. (b) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299 8.(a) De Koning, H.; Speckamp, W. N. In Houben-Weyl, Methods in Organic Chemistry, Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E21b, 1953-2009. (b) Bailey, P. D.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 7115. (c) Inouye, Y.; Tazawa, N.; Watanabe, A.; Aoki, Y.; Kakisawa, H. Bull. Chem. Soc. Jpn 1992, 65, 2866. (d) Yoda, H.; Kitayama, H.; Yamada, W.; Katagiri, T.; Takabe, K. Tetrahedron: Asymmetry 1993, 4, 1451. (e) Huang, P. Q.; Wang, S. L.; Ye, J. L.; Ruan, Y. P.; Huang, Y. Q.; Zheng, H.; Gao, J. X. Tetrahedron 1998, 54, 12547. 9.Wrobel, J. T.; Cybulski, J.; Dabrowski, Z. Synthesis 1977, 686. 10.Evans, D. A.; Thomas, E. W.; Cherpeck, R. E. J. Am. Chem. Soc. 1982, 104, 3695. 11.Collado, M. I.; Sotomayor, N.; Villa, M. J.; Lete, E. Tetrahedron Lett. 1996, 37, 6193. 12.Maldaner, A.; Pilli, R. A. Tetrahedron 1999, 55, 13321. 13.Liu, L. X.; Ruan, Y. P.; Guo, Z. Q.; Huang, P. Q. J. Org. Chem. 2004, 69, 6001. 14.(a) Hsu, R. T.; Cheng, L. M.; Chang, N. C.; Tai, H. M. J. Org. Chem. 2002, 67, 5044. (b) Chang, B. R.; Chen, C. Y. Chang, N. C. Tetrahedron Lett. 2002, 43, 3233–3235. 15.Chen, C. Y.; Chang, B. R.; Tsai, M. R.; Chang, N. C. Tetrahedron 2003, 59, 9383. 16.Tsai, M. R.; Sun, P. P.; Chang, M. Y.; Chang, N. C. J. Chin. Chem. Soc. 2004, 51, 613. 20.Wu, B. G.; Bai, D. G. J. Org. Chem. 1997, 62, 5978. 21.Tsai, M. R.; Chen, B. F.; Cheng, C. C.; Chang, N. C. Org. Lett. To be communicate |
電子全文 Fulltext |
本電子全文僅授權使用者為學術研究之目的，進行個人非營利性質之檢索、閱讀、列印。請遵守中華民國著作權法之相關規定，切勿任意重製、散佈、改作、轉貼、播送，以免觸法。 |
紙本論文 Printed copies |
紙本論文的公開資訊在102學年度以後相對較為完整。如果需要查詢101學年度以前的紙本論文公開資訊，請聯繫圖資處紙本論文服務櫃台。如有不便之處敬請見諒。 開放時間 available 已公開 available |
QR Code |
國立中山大學 圖書與資訊處 │ 諮詢服務：2452 論文審查小組 │ 服務信箱 │ 系統開發維運：圖資處知識創新組
Office of Library and Information Services, National Sun Yat-sen University │ Contact Us : 2452 Thesis Format Review Team , Mail │ Development and operations : Knowledge Innovation Division, LIS