博碩士論文 103223060 詳細資訊




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姓名 鍾民敬(Min-Jing Zhong)  查詢紙本館藏   畢業系所 化學學系
論文名稱 金屬催化含氮炔類的合環反應之探討
檔案 [Endnote RIS 格式]    [Bibtex 格式]    至系統瀏覽論文 (2018-9-1以後開放)
摘要(中) 我們以鈀金屬及金金屬化合物成功催化含氮炔類化合物( o-alkynyl sulfonamide )進行分子內合環形成環己烷取代吡咯衍生物( 3a,4,5,6,7,7a-hexahydro-indoles ),炔類上有不同的取代基團時皆可有不錯的產率。
摘要(英) The Pd(II) or Au(I)-catalyzed intramolecular cyclization reactions of aliphatic amino alkynes to nonaromatic nitrogen heterocycles( 3a,4,5,6,7,7a-hexahydro-indoles )were accomplished. We also found that both aryl and alkyl groups on the alkynes underwent the cyclization with moderate to good yields.
關鍵字(中) ★ 合環反應
★ 金屬催化
關鍵字(英)
論文目次 總目錄
中文摘要 ..................................................................................................I
英文摘要 ................................................................................................ II
總目錄...................................................................................................III
圖目錄....................................................................................................V
流程圖目錄...........................................................................................VI
表目錄................................................................................................. VII
附圖目錄 ............................................................................................VIII
第一章 序論 ...........................................................................................1
1-1 前言...............................................................................................1
1-2 含氮雜環的合成...........................................................................3
1-3 研究動機.......................................................................................8
第二章 結果與討論...............................................................................9
2-1 起始物的製備...............................................................................9
2-1-1 直鏈含氮炔類的合成..............................................................9
2-1-2 環己烷取代含氮炔類的合成................................................11
2-2 金屬催化合環反應的結果..........................................................16
2-2-1 鈀金屬催化直鏈含氮炔類的合環反應.................................16
IV
2-2-2 鈀金屬催化環己烷取代含氮炔類的合環反應......................19 2-2-3 金金屬催化環己烷取代含氮炔類的合環反應.....................21
2-2-4 往具生物活性化合物之結構接近的後續步驟......................26
第三章 結論 .........................................................................................30
第四章 實驗部分.................................................................................31
4-1溶媒及處理過程..........................................................................31
4-2實驗器材與儀器..........................................................................32
4-3實驗步驟......................................................................................35
第五章參考文獻 ...............................................................................100
參考文獻 1. (a) Brion, F.; Marie, C.; Mackiewicz, P.; Roul, J. M.; Buendia, J. Tetrahedron Lett. 1992, 33, 4889-4892. (b) Shionoiri, H.; Takasaki, I.; Minamisawa, K.; Ishizuka, H.; Konno, K.; Naganuma, H.; Sasahara, K.; Kawahara, Y. Hypertens Res. 2001, 24, 235-240.
2. (a) Morain, P.; Lestage, P.; Nanteuil, G. D.; Jochemsen, R.; Robin, J-L.; Guez, D.; Boyer, P-A. CNS Drug Rev. 2002, 8, 31-52. (b) Bellemère1, G.; Morain, P.; Vaudry, H.; Jégou1, S. J. Neurochem. 2003, 84, 919-929. (c) Bellemère1, G.; Vaudry1, H. Morain, P.; Jégou1, S. J. Neiroendocrinol. 2005, 17, 306-313.
3. (a) Murakami, M.; Okita, Y.; Matsuda, H.; Okino1, T.; Yamaguchi, K. Tetrahedron Lett. 1994, 35, 3129-3132. (b) Murakami, M.; Ishida, K.; Okino, T.; Okita, Y.; Matsuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 2785-2788. (c) Rios Steiner, J. L.; Murakami, M.; Tulinsky, A. J. Am. Chem. Soc. 1998, 120, 597-598 (d) Kodani, S.; Ishida, K.; Murakami, M. J. Nat. Prod. 1998, 61, 1046-1048. (e) Ishida, K.; Okita K.; Matsuda, H.; Okino, T.; Murakami, M. Tetrahedron 1999, 55, 10971-10988. (f) Ersmark, K.; Del Valle, J. R.; Hanessian, S. Angew. Chem. Int. Ed. 2008, 47, 1202-1223.
4. (a) Valls, N.; López-Canet, M.; Vallribera, M.; Bonjoch, J. J. Am. Chem. Soc. 2000, 122, 11248-11249. (b) Valls, N.; López-Canet, M.; Vallribera, M.; Bonjoch, J. Chem. Eur. J. 2001, 7, 3446-3460. (c) Ohshima, T.; Gnanadesikan, V.; Shibuguchi, T.; Fukuta, Y.; Nemoto, T.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 11206-11207. (d) Fukuta, Y.; Ohshima, T.; Gnanadesikan, V.; Shibuguchi, T.; Nemoto, T.; Kisugi, T.; Okino, T.; Shibasaki, M. P. Natl. Acad. Sci. U.S.A. 2004, 101, 5433-5438. (e) Nie, X.; Wang, G. Tetrahedron 2008, 64, 5784-5793. (f) Wang, G.; Goyal, N.; Hopkinson, B. Bioorg. Med. Chem. Lett. 2009, 19, 3798-3803. (g) Sofack-Kreutzer, J.; Martin, N.; Renaudat, A.; Jazzar, R.; Baudoin, O. Angew. Chem. Int. Ed. 2012, 51, 10399-10402. (h) Dailler, D.; Danoun, G; Baudoin, O. Angew. Chem. Int. Ed. 2015, 54, 4919-4922.
5. (a) Valls, N.; Vallribera, M.; Carmeli, S.; Bonjoch, J. Org. Lett. 2003, 5, 447-450. (b) Ella-Menye, J-R.; Nie, X.; Wang, G. Carbohyd. Res.2008, 343, 1743-1753. (c) Hanessian, S.; Wang, X.; Ersmark, K.; Del Valle, J. R.; Klegraf, E. Org. Lett. 2009, 11, 4232-4235. (d) Trost, B. M.; Kaneko, T.; Andersen, N. G.; Tappertzhofen, C.; Fahr, B. J. Am. Chem. Soc. 2012, 134, 18944-18947. (e) Diethelm, S.; Schindler, C. S.; Carreira, E. M. Chem. Eur. J. 2014, 20, 6071-6080. (f) Dailler, D.; Danoun, G.; Ourri, B.; Baudoin, O. Chem. Eur. J. 2015, 21, 9370-9379.
6. (a) Hiroya, K.; Matsumoto, S; Sakamoto, T. Org. Lett. 2004, 6, 2953-2956. (b) Zhang, Z.; Tang, X.; Xu, Q.; Shi, M. Chem. Eur. J. 2013, 19, 10625-10631. (c) Zhdanko, A.; Maier, M. E. Chem. Eur. J. 2014, 20, 1918-1930. (d) Zhdanko, A.; Maier, M. E. Angew. Chem. Int. Ed. 2014, 53, 7760-7764. (e) Cheng, G.; Yang, D. Chin. J. Org. Chem. 2015, 35, 2023-2034. (f) Álvarez-Pérez1, A.; González-Rodríguez1, C.; García-Yebra, C.; Varela, J. A.; Oñate, E.; Esteruelas, M. A.; Saá, C. Angew. Chem. Int. Ed. 2015, 54, 13357-13361. (g) Zhang, Z.; Xiao, F.; Huang, B.; Hu, J.; Fu, B.; Zhang, Z. Org. Lett. 2016, 18, 908-911. (h) Yamauchi, T.; Shibahara, F.; Murai, T. Tetrahedron Letters 2016, 57, 2945-2948.
7. (a) Jones, A. D.; Knight, D. W.; Hibbs, D. E. J. Chem. Soc., Perkin Trans. 1 2001, 1182-1203. (b) Ding, C. H.; Daia, L. X.; Hou, X. L. Tetrahedron 2005, 61, 9586-9593.
8. (a) Faulkner, A.; Bower, J. F. Angew. Chem. Int. Ed. 2012, 51, 1675-1679. (b) Pantaine, L.; Coeffard, V.; Moreau, X.; Greck, C. Org. Lett. 2015, 17, 3674-3677.
9. (a) Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260-11261. (b) Hiroya, K.; Matsumoto, S.; Ashikawa, M.; Ogiwara, K.; Sakamoto, T. Org. Lett. 2006, 8, 5349-5352.
10. Xia, Y.; Huang, G. J. Org. Chem. 2010, 75, 7842-7854.
11. (a) Andreev, I. A.;Belov, D. S.; Kurkin, A. V.;Yurovskaya, M. A. Eur. J. Org. Chem. 2013, 649-652. (b) Tsukamoto, H.;Shiraishi, M.; Doi, T. Org. Lett. 2013, 15, 5932-5935.
11. (a) Huple, D. B.; Liu R-S. ChemCatChem 2015, 7, 2824-2825. (b) Archambeau, A.; Rovis, T. Angew. Chem. Int. Ed. 2015, 54, 13337-13340.
13. (a) Millar, J. G.; McElfresh, J. S.; Romero, C.; Vila, M.; Marí-Mena, N.; Lopez-Vaamonde, C. J. Chem. Ecol. 2010, 36, 923-932. (b) Herndon, J. W.; Matasi, J. J. J. Org. Chem. 1990, 55, 786-788.
14. Barks, J. M.; Weingarten, G. G.; Knight, D. W. J. Chem. Soc., Perkin Trans. 1 2000, 3469-3476.
15. Zhang, Z.; Wu, L.; Liao, J. Wu, W.; Jiang, H.; Li, J.; Li, J. J. Org. Chem. 2015, 80, 7594-7603.
16. Rimoldi, M.; Ragaini, F.; Gallo, E.; Ferretti, F.; Macchib, P.; Casati, N. Dalton Trans. 2012, 41, 3648-3658.
17. van Esseveldta, B. C. J.; van Delfta, F. L.; Smitsb J. M. M.; de Gelderb, R.; Rutjes, F. P. J. T. Synlett 2003, 15, 2354-2358.
18. (a) Davis, F. A.; Ramachandar, T.; Liu, H. Org. Lett. 2004, 6, 3393-3395. (b) Nadano, R.; Iwai, Y.; Mori, T.; Ichikawa, J. J. Org. Chem. 2006, 71, 8748-8754. (c) Fritz, S. P.; Matlock, J. V.; McGarrigle, E. M.; Aggarwal, V. K. Chem. Eur. J. 2013, 19, 10827-10831.
19. (a) Nuhricha, A.; Moulines, J. Tetmhedron 1991, 47, 3075-3088. (b) Moriyama, K.; Izumisawa, Y.; Togo, H. J. Org. Chem. 2012, 77, 9846-9851.
20. (a) Henning, R.; Urbach, H. Tetrahedron Letters 1983, 24, 5339-5342. (b) Barton, D. H. R.; Guilhem, J.; Herve, Y.; Potier, P.; Thierry, J. Tetrahedron Letters 1987, 28, 1413-1416. (c) Brion, F.; Marie, C.; Mackiewicz, P.; Roul, J. M.; Buendia, J. Tetrahedron Letters 1992, 33, 4889-4892. (d) Belvisi, L.; Colombo, L.; Colombo, M.; Giacomo, D. M.; Manzoni, L.; Vodopivec, B.; Scolastico, C. Tetrahedron 2001, 57, 6463-6473. (e) Gallos, J. K.; Sarli, V. C.; Massen, Z. S.; Varvogli, A. C.; Papadoyanni, C. Z.; Papaspyrou S. D.; Argyropoulos, N. G. Tetrahedron 2005, 61, 565-574.
21. Jurberg, I. D.; Odabachian, Y.; Gagosz, F. J. Am. Chem. Soc. 2010, 132, 3543-3552.
22. Choi, S. R.; Breugst, M.; Houk, K. N.; Poulter, C. D. J. Org. Chem. 2014, 79, 3572-3580.
指導教授 侯敦仁(Duen-Ren Hou) 審核日期 2016-8-26
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