簡易檢索 / 詳目顯示

研究生: 周柏坤
Chou, Po-Kun
論文名稱: 3-芳香基-4-甲醯雪梨酮硫半卡腙之環化反應研究
Studies on the Cyclization Reactions of 3-Aryl-4-Formylsydnone Thiosemicarbozones
指導教授: 葉茂榮
Yeh, Mou-Yung
學位類別: 碩士
Master
系所名稱: 理學院 - 化學系
Department of Chemistry
論文出版年: 2002
畢業學年度: 90
語文別: 中文
論文頁數: 69
中文關鍵詞: 硫半卡腙雪梨酮
外文關鍵詞: thiosemicarbozones
相關次數: 點閱:71下載:1
分享至:
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
  •   雪梨酮化合物因為特殊的電子分布所以反應性也不同於一般的化合物,此外雪梨酮化合物常具有生理活性或藥理性質,而有一些雪梨銅衍生物已被報導出具有藥理作用,例如:鎮靜、抗菌性...等作用,於是本研究設計將具有藥理性質的雜環和雪梨酮環相互結合,期盼合成具有更佳生理或藥理作用的雪梨酮雜環化合物。
      本研究利用3-芳香基-4-甲醯雪梨酮硫半卡腙化合物為反應前驅物,再和我們慎選的一系列環化試劑進行反應,而環化試劑有順丁烯二酸酐、氯醋酸以及氯化鐵等三種試劑,藉此可以得到具有四氫及硫二環的雪梨酮雜環化合物。
    本研究主要包括如下:
    1.3-芳香基-4-甲醯雪梨酮硫半卡腙與順丁烯二酸酐之環化反應
    2.3-芳香基-4-甲醯雪梨酮硫半卡腙與氯醋酸之環化反應
    3.3-芳香基-4-甲醯雪梨酮硫半卡腙與氯化鐵之環化反應

      The reactivity of sydnones is different from normal compounds as a result of their peculiar distribution of electrons. Furthermore, sydnone often possess biological and pharmacological activities. And some of the sydnone derivatives have been reported to possess pharmacological activities, for example, sedative, antibacterial…etc. Consequently, this study attempt to combine heterocyclic compounds possessing pharmacological activities with sydnones, we have designed the synthesis of some heterocyclic sydnone possessing better biological and pharmacological activities.
      In our study, 3-aryl-4-formyl-sydnone thiosemicarbazones act as precursors, and react with a series of cyclic agents. The three cyclic agents are maleic anhydride, chloroacetic acid and ferric chloride, from which we can obtain heterocyclic sydnones that possess thiazolidine and thiadiazole groups.
      The three major parts in this research are summarized as follows:
    1.The cyclic reactions of 3-aryl-4-formyl-sydnone thiosemicarbazones with maleic anhydride.
    2.The cyclic reactions of 3-aryl-4-formyl-sydnone thiosemicarbazones with chloroacetic acid.
    3.The cyclic reactions of 3-aryl-4-formyl-sydnone thiosemicarbazones with ferric chloride.

    中文摘要…………………………………………………………………Ⅰ 英文摘要…………………………………………………………………Ⅱ 第一章 雪梨酮化合物之簡介 一、前言…………………………………………………………………1 二、雪梨酮化合物之合成………………………………………………3 三、雪梨酮的反應性……………………………………………………5 四、研究之目的…………………………………………………………15 第二章 3-芳香基-4-甲醯雪梨酮硫半卡腙衍生物與順丁烯二酸酐之環化反應 一、前言…………………………………………………………………16 二、結果與討論…………………………………………………………18 三、實驗部分……………………………………………………………23 第三章 3-芳香基-4-甲醯雪梨酮硫半卡腙衍生物與氯醋酸之環化反應 一、前言…………………………………………………………………31 二、結果與討論…………………………………………………………35 三、實驗部分……………………………………………………………39 第四章 3-芳香基-4-甲醯雪梨酮硫半卡腙衍生物與氯化鐵之環化反應 一、前言…………………………………………………………………46 二、結果與討論…………………………………………………………52 三、實驗部分……………………………………………………………56 第五章 結論………………………………………………………………63 參考文獻…………………………………………………………………65

    1.Earl, J. C.; Mackney, A. W., J. Chem. Soc., 1935, 899.

    2.Simpson, J. C. E., J. Chem. Soc., 1946, 94.

    3.Baker, W.; Ollis, W. D.; Poole, V. D., J. Chem. Soc., 1949, 307.

    4.Farbenfabriken Bayer Akt-Ges., British Patent., 1958, 823, 001; C.A., 1965, 63, 7605.

    5.Wright, D. P.; Licr, J. J.; Frazza, E. J., German Patent., 1959, 1097, 751; C.A., 1962, 56, 10639.

    6.Smith, A. E.; Riddell, J. A., German Patent., 1961, 1, 120, 800; C.A., 1962, 56, 15868.

    7.Greco, C. V.; Nyberg, W. H.; Cheng, C. C., J. Med. Pharm. Chem., 1962, 5, 861.

    8.Rogers, E. F.; Davis, D., U.S. Patent., 1965, 3, 189, 520; C.A., 1965, 63, 7605.

    9.Ackerman, E., Acta. Biol. Med. Ger., 1966, 17(4), 498; C.A., 1967, 66, 17685W.

    10.Imashiro, Y.; Masuda, K., Japan Patent., 1969, 69, 32411;C.A., 1970, 72, 111482q.

    11.Hahn, S. J.; Kim, S. H.; Chane, H. J.; Youn, L. H.; Lyu, H. S., Bull. Korean Chem. Soc., 1988, 8, 49.

    12.Huseya, Y.; Chinone, A.; Ohta, M., Bull. Chem. Soc .Jpn., 1971, 44, 1667.

    13.Huseya, Y.; Chinone, A.; Ohta, M., Bull. Chem. Soc. Jpn., 1972, 45, 3202.

    14.Bhat, V,; Dixit, V. M.; Ugarker, B. G.; Trozzolo, A. M.; George, M. V., J. Org. Chem., 1979, 44, 2957.

    15.Gotthardt, H.; Reiter, F., Chem. Ber., 1979, 112, 1193.; cf.C.A. 91, 5155t.

    16.Tien, J. M.; Hunsberger, I. M., J. Am. Chem. Soc., 1955, 77, 1843.

    17.Shetty, B. V., J. Org. Chem., 1961, 26, 3002.

    18.Baker, W.; Ollis, W. D.; Poole, V. D., J. Chem. Soc. ,1949, 307.

    19.Earl, J. C., Tetrahedron., 1957, 1, 338.

    20.Huisgen, R.; Gotthardt, H.; Grashey, R., Angew. Chem., 1962, 74, 30.

    21.Gotthardt, H.; Huisgen, R., Chem. Ber., 1968, 101, 552.

    22.Stille, J. K.; Harris, F. W.; Bedford, M. A., J. Heterocyclic Chem., 1966, 3, 55.

    23.Gotthardt, H.; Teiter, F., Chem. Ber., 1979, 112, 1193.

    24.Gotthardt, H.; Teiter, F., Chem. Ber., 1979, 112, 1635.

    25.Kato, H.; Sato, S.; Ohta, M., Tetrahedron Lett., 1967, 4261.

    26.Stansfield, F., J. Chem. Soc., 1958, 4781.

    27.Greco, C. V.; Pesce, M.; Franco, J. M., J. Heterocyclic Chem., 1966, 3. 391.

    28.Turnbull, K. J., J. Heterocyclic Chem., 1985, 22. 965

    29.Tien, H. J.; Nonaka, T.; Sekine, T., Chem. Lett., 1979, 283.

    30.Thoman, C. J.; Voaden, D. J.; Hunsberger, I. M., J. Org. Chem., 1964, 29, 2044.

    31.Dallacker, F.; Kern, J., Chem. Ber., 1966, 99, 3830.

    32.Masuda, K.; Kikuchi, K.; Imajo, Y., Japan Patent., 1972, 29, 511.

    33.Yeh, M. Y.; Tien, H. J.; Huang, L. Y.; Chen, M. H., J. Chin. Chem. Soc., 1983, 30, 29.

    34.Jugie, G.; Smith, J. A. S.; Martin, G. J., J. Chem. Soc., Perkin Trans.1, 1975, 2, 925.

    35.Tien, H. J.; Yen, M. Y.; Wu, C. H.; Chen, H. T., J. Chin. Chem. Soc., 1984, 31, 191.

    36.Putezer, B.; Hamelin, W.; Katz, J., J .Am. Chem. Soc., 1951, 73, 2958.

    37.陳光伯 國立成功大學化學研究所碩士論文 2001

    38.Dudenko, R. G.; Pelkis, P. S., Khimiya Getersiklicheskikh Soedinenii., 1967, 3, 91.

    39.Dudenko, R. G.; Gorbenko, E. F., Chem. Heterocyclic Compd., 1975, 11, 301.

    40.Gruttadauvia, M.; Buccheri, F.; Werber, A., J. heterocyclic Chem., 1993, 30, 765.

    41.Kubota, S.; Ueda, Y.; Fujkane, K.; Toyooka, K.; Shibuya, M., J. Org. Chem., 1980, 45, 1473.

    42.Smolanka, I. V.; Man’o, N. P.; Krasnitskaya, T. A., Chem. Heterocyclic Compd., 1981, 17, 457.

    43.Krbavcic. A., J. Med. Chem., 1966, 9, 430.

    44.Troutman, M. D.; Long, L. M., J. Amer. Chem. Soc., 1948, 70, 3436.

    45.Surrey, A. R., J. Amer. Chem. Soc., 1949, 71, 3105.

    46.Surrey, A. R., J. Amer. Chem. Soc., 1949, 71, 3354.

    47.Joshi, K. C.; Gupta, J. S., Indian J. Chem., 1967, 5, 139.

    48.Agrawal, A. K.; Rastogi, V. K.; Parmar. S. S., J. Heterocyclic Chem., 1978, 15, 677.

    49.Mucchi, L.; Vecchia, F. D., J. Heterocyclic Chem., 1982, 19, 557.

    50.Shan, S. J.; Shan, S. R.; Desai, N. C.; Thaker, K. A., J. Indian Chem. Soc., 1984, 61, 648.

    51.Dave, M. P.; Patel, M. J.; Langalia, N. A.; Thaker, K. A., J. Indian Chem. Soc., 1984, 61, 891.

    52.Gursoy, A.; Karah, N., Arzneim.-Forsch./Drug Res., 2000, 50, 167.

    53.Desai, N. C.; Shukla, H. K.; Thaker, K. A., J. Indian Chem. Soc., 1984, 61, 648.

    54.Surrey, A. R., J. Amer. Chem. Soc., 1947, 69, 2911.

    55.Satsumabayashi, A., Synthesis, 1977, 881.

    56.Skagius, K., Acta chem. Scand.., 1960, 14, 1054.

    57.Sen, A. B.; Gupta, S. K., J. Indian Chem. Soc., 1962, 39, 628.

    58.Bacchetti, T., Tetrahedron Lett., 1964, 6, 3569.

    59.Vakula, T. R., Indian J. Chem., 1969, 7, 577.

    60.Shegal, L. M.; Shegal, I. L., Chem. Heterocyclic. Compd., 1970, 6, 1238.
    61.Malbec, F.; Milcent, R.; Barbier, G., J. Heterocyclic Chem., 1984, 21, 1689.

    62.Mohammad, R.; Verma, V. K., Synthesis, 1985, 17, 691.

    63.Elsayed, S. H.; Mahmoud, A. N; Yeldez, E. K.; Ahmed, M., Bull. Chem. Soc. Jpn., 1987, 60, 3405.

    64.Likhate, M. A.; Fernandes, P. S., J. Indian Chem. Soc., 1992, 69, 596.

    65.Zhang, Z. Y.; Sun, X. W.; Chu, C. H.; Zhao, L., J. Chin. Chem. Soc., 1997, 44, 535.

    66.Lu, S. M; Chen, R. Y., Synth. commun., 1999, 29, 3443.

    67.Li, Z.; Wang, X.; Da, Y., Synth. commun., 2001, 31, 1829.

    68.Supuran, C. T.; Briganti, F.; Tilli, S.; Chegwidden, W. R.; Scozzafava, A., Bioorganic & Medicinal Chemistry., 2001, 9, 703.

    69.Sandstrom, J., Acta chem. Scand.., 1960, 14, 1939.

    70.Radha, V. T.; Ranga, R. V.; Srinivasan, V. R., Indian J. chem.., 1969, 7, 577.

    71.Milcent, R.; Nguyen, T. H., J. Heterocyclic .Chem.., 1986, 23, 881.

    下載圖示 校內:立即公開
    校外:2002-07-05公開
    QR CODE