| 研究生: |
詹詠翔 Yung-Hsiang Chan |
|---|---|
| 論文名稱: |
鈀金屬催化含氮炔類的合環反應之探討 Palladium catalyzed intramolecular cyclization of N-(2-ethynylcyclopentyl)sulfonamide |
| 指導教授: | 侯敦仁 |
| 口試委員: | |
| 學位類別: |
碩士 Master |
| 系所名稱: |
理學院 - 化學學系 Department of Chemistry |
| 論文出版年: | 2017 |
| 畢業學年度: | 105 |
| 語文別: | 中文 |
| 論文頁數: | 267 |
| 中文關鍵詞: | 鈀金屬催化含氮炔類的合環反應之探討 |
| 相關次數: | 點閱:17 下載:0 |
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| 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 |
我們成功以鈀金屬催化含氮炔類化合物進行分子內合環形成環戊
烷取代吡咯衍生物,且使用微波反應器輔助可以有效提升產率,最高可
達92%。此方法可應用於合成藥物Ramipril 中的重要結構。
Hydroamination of N-(2-ethynylcyclopentyl)sulfonamide to
give non-aromatic 2,3-dihydropyrroles was achieved by using
PdCl2 as the catalyst. With microwave-assisted heating, up to 92%
isolated yield was obtained from this intramolecular 5-endodig
cyclization. The cyclopentane-fused 2,3-dihydropyrroles were
transformed into the corresponding N-tosyl-pyrrolidine-2-
carboxylic acids.
第五章 參考文獻
1. (a) Comprehensive Heterocyclic Chemistry III, ed. A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven and R. J. K. Taylor, Elsevier Science, 2008, vol. 3; (b) J. A. Joule and K. Mills, in Heterocyclic Chemistry, John Wiley & Sons, 2010, pp. 587–608; (c) J. Bergman and T. Janosik, in Modern Heterocyclic Chemistry, ed. J. Alvarez-Builla, J. J. Vaquero and J. Barluenga, Wiley-VCH, 2011, ch. 4.
2. (a) D. C. Peters, S. Noble and G. L. Plosker, Drugs, 1998, 56, 871; (b) F. Brion, C. Marie, P. Mackiewicz, J. M. Roul and J. Buendia, Tetrahedron Lett., 1992, 33, 4889; (c) H. Shionoiri, I. Takasaki, K. Minamisawa, H. Ishizuka, K. Konno, H. Naganuma, K. Sasahara and Y. Kawahara, Hypertens. Res., 2001, 24, 235.
3. (a) J. E. Frampton and D. H. Peters, Drugs, 1995, 49, 440; (b) G. C. M. Kondaiah, M. Vivekanandareddy, L. A. Reddy, S. A. Anurkar, V. M. Gurav, M. Ravikumar, A. Bhattacharya and R. Bandichhor, Synth. Commun., 2011, 41, 1186.
4. (a) P. Morain, P. H. Boeijinga, A. Demazieres, G. De Nanteuil and R. Luthringer, Neuropsychobiology, 2007, 55, 176; (b) G. Bellemere, P. Morain, H. Vaudry and S. Jegou, J. Neurochem., 2003, 84, 919; (c) P. Morain, P. Lestage, G. D. Nanteuil, R. Jochemsen, J.-L. Robin, D. Guez and P.-A. Boyer, CNS Drug Rev., 2002, 8, 31.
5. (a) M. Murakami, Y. Okita, H. Matsuda, T. Okino and K. Yamaguchi, Tetrahedron Lett., 1994, 35, 3129; (b) M. Murakami, K. Ishida, T. Okino, Y. Okita, H. Matsuda and K. Yamaguchi, Tetrahedron Lett., 1995, 36, 2785; (c) J. L. Rios Steiner, M. Murakami and A. Tulinsky, J. Am. Chem. Soc., 1998, 120, 597; (d) S. Kodani, K. Ishida and M. Murakami, J. Nat. Prod., 1998, 61, 1046; (e) K. Ishida, K. Okita, H. Matsuda, T. Okino and M. Murakami, Tetrahedron, 1999, 55, 10971; (f ) K. Ersmark, J. R. Del Valle and S. Hanessian, Angew. Chem., Int. Ed., 2008, 47, 1202.
6. Recent examples catalyzed by Pd: (a) M. Jash, B. Das and C. Chowdhury, J. Org. Chem., 2016, 81, 10987; (b) E. A. Filatova, A. F. Pozharskii, A. V. Gulevskaya and V. A. Ozeryanskii, J. Org. Chem., 2015, 80, 872; (c) B. Yao, Q. Wang and J. Zhu, Chem. – Eur. J., 2015, 21, 7413; (d) R. Shen, T. Kusakabe, K. Takahashi and K. Kato, Org. Biomol. Chem., 2014, 12, 4602; (e) C. Zheng, J. J. Chen and R. Fan, Org. Lett., 2014, 16, 816; (f ) G. Xia, X. Han and X. Lu, Org. Lett., 2014, 16, 2058; (g) B. Yao, Q. Wang and J. Zhu, Chem. – Eur. J., 2014, 20, 12255; (h) D. Janreddy, V. Kavala, C.-W. Kuo, T.-S. Kuo, C.-H. He and C.-F. Yao, Tetrahedron Lett., 2013, 69, 3323; (i) X.-F. Xia, N. Wang, L.-L. Zhang, X.-R. Song, X.-T. Liu and Y.-M. Liang, J. Org. Chem., 2012, 77, 9163.
7. Recent examples catalyzed by Cu: (a) S. Cacchi, G. Fabrizi and L. M. Parisi, Org. Lett., 2003, 5, 3843; (b) K. Hiroya, S. Itoh and T. Sakamoto, J. Org. Chem., 2004, 69, 1126; (c) N. Matsuda, K. Hirano, T. Satoh and M. Miura, J. Org. Chem., 2012, 77, 617; (d) J. Gao, Y. Shao, J. Zhu, J. Zhu, H. Mao, X. Wang and X. Lv, J. Org. Chem., 2014, 79, 9000; (e) J. Gao, Y. Shao, J. Zhu, J. Zhu, H. Mao, X. Wang and X. Lv, J. Org. Chem., 2014, 79, 9000; (f ) Y. Xing, G. Sheng, J. Wang, P. Lu and Y. Wang, Org. Lett., 2014, 16, 1244; (g) J. Tang, B. Xu, X. Mao, H. Yang, X. Wang and X. Lv, J. Org. Chem., 2015, 80, 11108; (h) J. Yu, D. Zhang-Negrerie and Y. Du, Org. Lett., 2016, 18, 3322; (i) H. E. Ho, K. Oniwa, Y. Yamamoto and T. Jin, Org. Lett., 2016, 18, 2487.
8. Recent examples catalyzed by Au: (a) K. C. Majumdar, S. Hazra and B. Roy, Tetrahedron Lett., 2011, 52, 6697; (b) K. Hirano, Y. Inaba, N. Takahashi, M. Shimano, S. Oishi, N. Fujii and H. Ohno, J. Org. Chem., 2011, 76, 1212; (c) M. Muuronen, J. E. Perea-Buceta, M. Nieger, M. Patzschke and J. Helaja, Organometallics, 2012, 31, 4320; (d) O. S. Morozov, A. V. Lunchev, A. A. Bush, A. A. Tukov, A. F. Asachenko, V. N. Khrustalev, S. S. Zalesskiy, V. P. Ananikov and M. S. Nechaev, Angew. Chem., Int. Ed., 2013, 52, 11835; (e) P. P. Sharp, M. G. Banwell, J. Renner, K. Lohmann and A. C. Willis, Org. Lett., 2013, 15, 2616; (f) J. E. Perea-Buceta, T. Wirtanen, O.-V. Laukkanen, M. K. Mäkelä, M. Nieger, M. Melchionna, N. Huittinen, J. A. Lopez-Sanchez and J. Helaja, Angew. Chem., Int. Ed., 2013, 52, 11835; (g) B. V. S. Reddy, M. R. Reddy, S. Yarlagadda, C. R. Reddy, G. R. Kumar, J. S. Yadav and B. Sridhar, J. Org. Chem., 2015, 80, 8807; (h) S. Liang, L. Hammond, B. Xu and G. B. Hammond, Adv. Synth. Catal., 2016, 358, 3313.
9. (a) S. Miaskiewicz, J.-M. Weibel, P. Pale and A. Blanc, Org. Lett., 2016, 18, 844; (b) S. Miaskiewicz, B. Gaillard, N. Kern, J.-M. Weibel, P. Pale and A. Blanc, Angew. Chem., Int. Ed., 2016, 55, 9088; (c) A. Galván, J. Calleja, F. J. Fañanás and F. Rodríguez, Chem. – Eur. J., 2015, 21, 3409; (d) Y.-F. Yu, C. Shu, B. Zhou, J.-Q. Li, J.-M. Zhou and L. W. Ye, Chem. Commun., 2015, 51, 2126; (e) W. V. Rossom, Y. Matsushita, K. Ariga and J. P. Hill, RSC Adv., 2014, 4, 4897.
10. (a) O. Mitsunobu, Synthesis, 1981, 1; (b) J. M. Barks, G. G. Weingarten and D. W. Knight, J. Chem. Soc., Perkin Trans. 1, 2000, 3469.
11. A. Zhdanko and M. E. Maier, Angew. Chem., Int. Ed., 2014, 53, 7760
12. B. C. J. van Esseveldta, F. L. van Delfta, J. M. M. Smitsb, R. de Gelderb and F. P. J. T. Rutjes, Synlett, 2003, 2354.
13. A. Nuhricha and J. Moulines, Tetrahedron, 1991, 47, 3075.