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研究生: 顏澤卉
論文名稱: 利用微波輔助合成一系列具有特殊藥性色烯類化合物 ;利用簡單且高效率的方式藉由一鍋化合成3-羥基與3-胺基黃酮類衍生物
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: 2010
畢業學年度: 98
語文別: 中文
論文頁數: 280
中文關鍵詞: 微波
論文種類: 學術論文
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  • 本論文主要分為兩部分,第一部分是在探討藉由微波反應器輔助且在不添加催化劑條件下,將硫醇類化合物、丙二腈與2-羥基苯甲醛合成屬於著名先驅藥物之一的Chromenopyridine為骨架之化合物,其具有多種生物活性及藥理作用。
    第二部分利用微波反應器透過一鍋化合成具生物活性3-氫氧基及3-氨基-2-苯基-4H-色烯-4-酮類化合物,本實驗主要是由3-硝基-2H-色烯類衍生物經反應後獲得中間物diethyl-4-ethoxy-3-(hydroxyimino) -2-phenylchroman-4-ylphosphonatey在乙醇作為溶劑於迴流條件下獲得產物。中間物以及產物結構已由XRD被確認。

    The first part of this dissertation describes the microwave assisted , one pot catalyst-free synthesis of chromenopyridine derivatives which achieved from the reaction of thiols, malononitrile and salicyaldehyde derivatives . The chromenopyridine derivatives framework is one of the well know privileged medicinal scaffolds diverse biological and pharmacological.
      The second part describes microwave promoted a novel and highly convenient approach for one-pot synthesis of 3-hydroxy and 3-amino-2-phenyl-4H-chromen-4-one was achieved from 3-nitro -2H-chromene derivatives via diethyl-4-ethoxy-3-(hydroxyimino) -2-phenylchroman-4-ylphosphonate in refluxing ethanol was developed. The structures of the prepared compounds were characterized by XRD method. The generality of this reaction was demonstrated by synthesizing an array of 3-hydroxy and 3-amino-2-phenyl-4H-chromen-4-one derivatives.

    壹、利用微波輔助合成一系列具有特殊藥性色烯類化合物 1-1、前言 1 1-1-1、多組成反應(Multicomponent reaction)的發展與應用 1 1-1-2、苯並吡喃(benzopyran)衍生物的介紹 7 1-1-3、微波輔助有機合成(Microwave-Assisted Organic Synthesis, MAOS) 12 1-2、研究目標 18 1-3、實驗結果與討論 19 1-3-1、利用微波反應器有效的合成Benzopyranpyridine 衍生物 20 1-3-2、結論 28 1-4、實驗部分 29 1-4-1、一般實驗方法 29 1-4-2、利用微波反應器有效的合成Benzopyranpyridine 衍生物實 驗步驟 31 1-5、參考文獻 32 1-6、光譜資料: 34 貳、利用簡單且高效率的方式藉由一鍋化合成3-羥基與3-胺基黃酮類 衍生物 2-1 前言 112 2-1-1、有機磷化學 112 2-1-2、亞磷酸衍生物的介紹及在有機合成上的應用 114 2-1-3、2H-硝基色烯類化合物的應用 120 2-1-4、類黃酮衍生物(Flavonoids)的發展及應用 122 2-2、研究目標 128 2-3、實驗結果與討論 129 2-3-1、一鍋化反應合成異黃酮類衍生物 129 2-3-2、結論 144 2-4、實驗部分 145 2-4-1、一般實驗方法 145 2-4-2、利用微波反應器有效的合成Benzopyranpyridine 衍生物實 驗步驟: 147 2-5、參考資料 148 2-6、光譜資料 150

    參考文獻
    1. Doemling, A. Org. Chem. Highlights 2004, April 5.
    2. “Towards the ideal synthesis”: Wender. P. A. ; Handy. S. T. ;Wright. D. L ; Chem. Ind. 1997, 765.
    3. (a) Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (b)Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415. (c) Orra, R. V. A.; de Greef, M. Synthesis 2003, 10, 1471. (d) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 21, 4101.
    4. Strecker, A.; Liebigs Ann. Chem. 1850, 75, 27.
    5. (a) Passerini, M.; Simone, L. Gazz. Chim. Ital. 1921, 51, 126. (b) Ferosie, I., Aldrichmica Acta. 1971, 4, 21.
    6. (a)Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (b)Yus, M.; Ramon, D. J. Angew. Chem. Int. Ed. 2005, 44, 1602 . (c) Alexander D. Chem. Rev, 2006, 106, 17. (d) Guo, K.; Thompson, M. J.; Chen, B-J. Med. Chem. 2008, 43, 93.
    7. Gao, S-J; Tsai, C- H.; Tseng, C.; Yao, C-F. Tetrahedron ,2008, 64, 9143.
    8. Curini, M.; Cravotto, G.; Epifano, F.; Giannone, G. Curr. Med. Chem. 2006, 13, 199.
    9. Perkin, W. H. J. Chem. Soc. 1877, 31, 388.
    10. Bradford, P. M., Michael, G. E., Frank, G. Favaloro, Jr., Named Reactions and Reagents in Organic Synthesis. John Wiley &Sons: New York. pp 490
    11. Isman, M.B.; Yan, J-Y. Naturwissenchaften. 1986, 73, 500.
    12. (a) Evans, B. E.; et al. J. Med. Chem. 1988, 31, 2235. (b) Patchett, A. A.; Nargund, R. P. Annu. Rep. Med. Chem. 2000, 35, 289. (c) poupaert, J.; Carato, P.; Colacino, E. Curr. Med. Chem. 2005, 12, 877.
    13. (a)Pfister, J. R.; Ferraresi, R. W.; Harrison, I. T.; Rooks, W. H.; Roszkowski, A. P.; Horn. A. V.; Fried, J. Id. J. Med. Chem. 1972, 15, 1032. (b) Pfister. J. R.; Ferraresi. R. W.; Harrison. I. T.; Rooks. W. H.; Fried, J. H. J. Med. Chem. 1978, 21, 669. (c) Barnes, A. C.; Hairsine,
    P. W.; Matharu, S. S.; Ramm, P. L.; Taylon, J. B. J. Med. Chem. 1979, 22, 418. (d) Ukawa, K.; Ishiguro, T.; Kuriki, H.; Nohara, A. Chem. Pharm. Bull. 1985, 33, 4432.
    14. (a) Maruyama, Y.; Terasawa, M.; Anami, K.; Kadobe, Y. Folia Pharmacol. Jpn. 1975, 71,857. (b) Goto, K; Terasawa, M.; Maruyama, Y. Intern. Arch. Allergy Appl. Immunol. 1979, 59, 13. (c) Terasawa, M.; Goto, K.; Maruyama, Y. Folia. Pharmacol. Jpn. 1982, 80, 417. (d) Oe, T.; Tsuruda, M.; Matsuo, H.; Terasawa, M.; Goto, K. Yukugaku Zasshi 1983, 103, 300.
    15. Bristol, J. A.; Gold, E. H.; Gross, I.; Lovey, R. G.; Long, J. F. J. Med. Chem. 1981, 24, 1010.
    16. Anderson, D. R.; Hegde, S.; Reinhard, E.; Gomez, L.; Vernier, W. F.; Lee, L.; Liu, S.; Sambandam, A.; Snider, P. A.; Masih, L. Bioorg. Med. Chem. Lett. 2005, 15, 1587.
    17. Arani Chanda, Valery V. Fokin. Chem. Rev. 2009, 109, 725.
    18. Ukawa, K.; Ishiguro, T.; Kuriki, H.; Nohara, A. Chem. Phram. Bull. 1995, 33, 4432.
    19. Frank J. V.; Thomas A. M,; Elizabeth A. W.; Janet H.; Louis L.L.; Mildred J. L,; William S.; Dhiru V.; Salvatore T. J. Med. Chem. 1975, 18, 1
    20. Kappe, C. O.; Stadler,A. Microwaves in Organic and Medicinal Chemistry; Wiley-VCH: Weinheim, 2005.
    21. (a) Gabriel, C.; Gabriel, S.; Grant, E. H.; Halstead, B. S.; Mingos,D.M. P. Chem. Soc. Rev. 1998, 27, 213. (b) Mingos, D. M. P.;Baghurst, D. R. Chem. Soc. Rev. 1991, 20, 1.
    22. (a) Gedye, R.; Smith, F.; Westaway, K.; Ali, H.; Baldisera,L.;Laberge, L.; Rousell, R. Tetrahedron Lett. 1986, 27, 279. (b)Giguere,R. J.; Bray, T. L.; Duncan, S. M.; Majetich, G. TetrahedronLett. 1986, 27, 4945.
    23. 蔡承軒,應用多組成反應策略合成色烯類及其他雜環化合物,國
    立台灣師範大學化學系碩士論文,民98[2009]
    24. Nikolai , M. E.; Artem, S. K.; Andrey, A. Y.; Mikhail , Y. A.; Igor,V. M.; Alexander K. Tetrahedron Lett. 2006, 47, 9309.

    參考資料
    1. (a) Baudler, M.; Glinka K. Chem. Rev. 1993, 93, 1623. (b) Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy, John Wiley & Sons, 1998.
    2. (a) Biliang, Z.; Zhiyong, C.; Lele S. Org. Lett., 2001, 3, 275. (b) Ivelitza, G.; Olke, C. U. Biochemistry 2008, 47, 12562.
    3. (a) Yavari, I.; Abbasinejad, M. A.; Hossaini, Z.; Org. Biomol. Chem. 2003, 1, 560 (b) Parthasarathy, J.; Gnanamani, S.; Paramasivan, P. T.; Synlett. 2009, 3, 917.
    4. Mucha, A.; Kafarski, P.; Tetrahedron Lett. 2002, 58, 5855.
    5. Maffei, M.; Buono, G.; Tetrahedron, 2003, 59, 8821.
    6. Arbuzova, S. N.; Gusarova, N. K.; Trofimov, B. A. Arkivoc. 2006, 5, 12.
    7. Kaboudin, B.; Nazari, R. Tetrahedron Lett. 2001, 42, 8211.
    8. Krueger,W. E.; McLean, M. B.; Rizwaniuk, A.; Maloney, J. R.; Behelfer, G. L.; Boland, B. E. J. Org. Chem, 1978, 43, 2877.
    9. Russell, G. A.; Yao, C.F.; J. Org. Chem. 1992, 57, 6508.
    10.Paleta, O.; Pomeisl, K.; Kafka, S.; Klásek, A.; Vladislav, K.; Bei. J. Org. Chem. 2005, 1, 17.
    11.(a) Penella, F. W.; Chen, S.-F.; Behrens, D. L.; Kaltenbach, R. F.; Seitzg, S. P. J. Med. Chem. 1994, 37, 2232.(b) Subramanian, S.; Desai, U. R. G.; Trivedi, K. Synth. Commun. 1990, 20, 1733.
    12.Habib, P. M.; Kavala, V.; Raju, B. R.; Kuo,C-W.; Huang, W-C; Yao, C-F. Eur. J. Org. Chem. 2009, 26, 4503.
    13.Virányi, A.; Marth, G.; Dancsó, A.; Blaskó, G.; To˝ke, L.; Nyerges, M. Tetrahedron 2006, 62, 8720.
    14.L Kürti, L.; Czakó B. Strategic applications of named reactions in organic synthesis, Elsevier B.V., 2004.
    15.Middleton, E., Jr. Effect of plant flavonoids on immune
    andinflammatory cell function. Adv. Exp. Med. Biol. 1998, 439, 175.
    16.Yang, C-S.; Lambert, J. D.; Hou, Z.; Ju, J.; Lu, G.; Hao, X. Molecular targets for the cancer preventive activity of tea polyphenols. Mol. Carcinog. 2006, 45, 431.
    17.(a) Harborne, J. B. The Flavonoids: Advances in Research since 1986; Chapman and Hall: London, 1994, 597. (b) Veitch, N. C.; Grayer, R. J. Nat. Prod. Rep. 2004, 21, 539. (c) Pietta, P. G. J. Nat. Prod. 2000, 63, 1035. (d)Cook, N. C.; Samman, S. J. Nutr. Biochem. 1996, 7, 66. (e)Cȅspedes, C. L.; Avila, J. G.; Martínez, A.; Serrato, B.; Mugica, J.
    C.C; Garciglia, R. J. Agric. Food Chem. 2006, 54, 3521.
    18.Ciesielska, E.; Studzian, K.; Zyner, E.; Ochocki, J.; Szmigiero, L. Cell. Biog. Mol. Lett. 2000, 5, 441. 19.Algar, J.; Flynn, J. P.; Proc. Roy. Irish Acad. 1934, 42, 1.
    20.(a) Oyamada, B.; J. Chem. Soc. Japan 1934, 55, 1256. (b) Oyamada, T. Bull. Chem. Soc. Jpn. 1935, 10, 182.
    21.Rao, T. S.; Singh, A. k.; Trivedi, G. K. Heterocycles, 1984, 22, 1377.
    22.Takechi, A.; Takikawa, H.; Miyake, H.; Sasaki, M. Chem. Lett. 2006,35, 128.

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