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研究生: 洪梓瑀
Hong, Zih-Yu
論文名稱: 2-碘苯胺衍生物和丙炔基二酮類/1-苯基-2-甲苯磺乙酮化合物經由銅催化分子內雙環化氧化級聯反應獲得3-羥基-3-呋喃基異茚二酮衍生物
Copper Catalyzed Oxidative Cascade Inter-Molecular Double Cyclisation of 2-Iodobenzamide Derivatives and Propagyl dicarbonyl/ 1-Phenyl-2-Tosylethanone Compounds for Accessing 3-Hydroxy-3-Furylisoindilinone Derivatives
指導教授: 姚清發
Yao, Ching-Fa
口試委員: 林文偉 姚清發 柳如宗
口試日期: 2021/07/25
學位類別: 碩士
Master
系所名稱: 化學系
Department of Chemistry
論文出版年: 2021
畢業學年度: 109
語文別: 中文
論文頁數: 103
中文關鍵詞: 3-羥基異吲哚啉酮銅催化
英文關鍵詞: copper catalyzed
DOI URL: http://doi.org/10.6345/NTNU202101288
論文種類: 學術論文
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  • 論文描述了3-羥基-3-呋喃基異吲哚啉酮衍生物的合成。本論文的內容分為兩章。第一章介紹了關於3-羥基異吲哚啉酮衍生物的藥用重要性和材料重要性的文獻綜述,以及構建3-羥基異吲哚啉酮衍生物的合成方法。
    第二部分說明了通過銅催化串聯雙環化從炔丙基二羰基化合物和2-碘苯甲酰胺衍生物生成3-羥基-3-呋喃基異吲哚啉酮衍生物的一鍋兩步法。此外,該方法通過探索2-炔基-2-苯磺醯基苯丙酮取代炔基二酮化合物得到3-羥基-2-苯基-3-(5-苯基-4-甲磺醯基)異吲哚啉酮衍生品。該方法相對較快、簡單、方便,可得到範圍廣泛的3-羥基-3-呋喃基異茚二酮衍生物。

    The thesis describes about the synthesis of 3-hydroxy-3-furylisoindolinone derivatives. The contents of this thesis are divided into two chapter. The first chapter describes about the literature review on about medicinal importance and material importance of 3-hydroxyisoindolinone derivatives also synthetic procedures for construction of 3-hydroxyisoindolinone derivatives. Further, the present chapter concludes with the aim of the thesis.
    The second part illustrates one-pot two-step method for the generation of 3-hydroxy-3-furylisoindolinone derivatives from propargyldicarbonyl compounds and 2-Iodobenzamide derivatives via copper catalyzed tandem double cyclization. Further, the methodology was extended by exploring the 2-proparyl-2-phenylsulfonyl-acetophenone by replacing propargyldicarbonyl compounds to obtain 3-hydroxy-2-phenyl-3-(5-phenyl-4-tosylfuran-2-yl)isoindolin-1-one derivatives. This method is relatively faster, simple and convenient to obtain a wide range of 3-hydroxy-3-furyl isoindenedione derivatives.

    目錄 中文摘要 I 英文摘要 II 1. 前言 1 1.1、呋喃(Furan)衍生物介紹 1 1.2、3-羥基異吲哚啉酮介紹 2 1.3、碸衍生物介紹 3 2、文獻回顧 4 2-1、呋喃衍生物合成 4 2-2、3-羥基異吲哚啉酮的合成 6 3.研究目標 8 4、實驗結果與討論 9 4-1、合成不同取代基的化合物 10 4-2、反應機構的探討 20 5、結論 26 6、實驗方法 27 6-1、分析儀器與基本實驗操作 27 6-2、實驗步驟 29 文獻回顧 33 光譜資料 36 光譜附圖 48

    1. Signoretto, M.; Menegazzo, F., On the Oxidation of Furfural to Furoic Acid. In Furfural: An Entry Point of Lignocellulose in Biorefineries to Produce Renewable Chemicals, Polymers, and Biofuels, World Scientific: 2018; pp 197-215.
    2. Banerjee, R.; Kumar, H.; Banerjee, M., Medicinal significance of furan derivatives: a review. International Journal of Research in Phytochemistry and Pharmacology 2015, 5 (3), 48-57.
    3. McAuley, J. B.; Herwaldt, B. L.; Stokes, S. L.; Becher, J. A.; Roberts, J. M.; Michelson, M. K.; Juranek, D. D., Diloxanide furoate for treating asymptomatic Entamoeba histolytica cyst passers: 14 years' experience in the United States. Clinical infectious diseases 1992, 15 (3), 464-468.
    4. Delsarte, A.; Faway, M.; Frère, J.-M.; Coyette, J.; Calberg-Bacq, C.-M.; Heinen, E., Nifurzide, a nitrofuran antiinfectious agent: interaction with Escherichia coli cells. Antimicrobial agents and chemotherapy 1981, 19 (3), 477-486.
    5. Yeomans, N. D.; Tulassay, Z.; Juhász, L.; Rácz, I.; Howard, J. M.; van Rensburg, C. J.; Swannell, A. J.; Hawkey, C. J., A comparison of omeprazole with ranitidine for ulcers associated with nonsteroidal antiinflammatory drugs. New England Journal of Medicine 1998, 338 (11), 719-726.
    6. Krause, T.; Gerbershagen, M.; Fiege, M.; Weisshorn, R.; Wappler, F., Dantrolene–a review of its pharmacology, therapeutic use and new developments. Anaesthesia 2004, 59 (4), 364-373.
    7. Fajardo, V.; Elango, V.; Cassels Niven, B.; Shamma, M., Chilenine: an isoindolobenzazepine alkaloid. 1981.
    8. Táborská, E.; Bochořáková, H.; Soušek, J.; Sedmera, P.; Vavrečková, C.; Šimánek, V., Fumaria densiflora DC. alkaloids. Collection of Czechoslovak chemical communications 1996, 61 (7), 1064-1072.
    9. Oladosu, I.; Zubair, M.; Ali, M.; Olawore, N., Anticandidal activity of volatile compounds from the root bark of Ficus exasperata Vahl-Holl (Moraceae). Journal of Essential Oil Bearing Plants 2009, 12 (5), 562-568.
    10. Suyavaran, A.; Ramamurthy, C.; Mareeswaran, R.; Shanthi, Y. V.; Selvakumar, J.; Mangalaraj, S.; Kumar, M. S.; Ramanathan, C. R.; Thirunavukkarasu, C., Synthesis and biological evaluation of isoindoloisoquinolinone, pyroloisoquinolinone and benzoquinazolinone derivatives as poly (ADP-ribose) polymerase-1 inhibitors. Bioorganic & medicinal chemistry 2015, 23 (3), 488-498.
    11. Hardcastle, I. R.; Ahmed, S. U.; Atkins, H.; Calvert, A. H.; Curtin, N. J.; Farnie, G.; Golding, B. T.; Griffin, R. J.; Guyenne, S.; Hutton, C., Isoindolinone-based inhibitors of the MDM2–p53 protein–protein interaction. Bioorganic & medicinal chemistry letters 2005, 15 (5), 1515-1520.
    12. Jaques, D. A.; Péchère-Bertschi, A.; Ponte, B., Chlortalidone: outdated or reborn? Cardiovascular Medicine 2016, 19 (12), 322-327.
    13. Konduru, N. K.; Dey, S.; Sajid, M.; Owais, M.; Ahmed, N., Synthesis and antibacterial and antifungal evaluation of some chalcone based sulfones and bisulfones. European journal of medicinal chemistry 2013, 59, 23-30.
    14. Shi, L.; Li, P.; Wang, W.; Gao, M.; Wu, Z.; Song, X.; Hu, D., Antibacterial activity and mechanism of action of sulfone derivatives containing 1, 3, 4-oxadiazole moieties on rice bacterial leaf blight. Molecules 2015, 20 (7), 11660-11675.
    15. Baunach, M.; Ding, L.; Willing, K.; Hertweck, C., Bacterial Synthesis of Unusual Sulfonamide and Sulfone Antibiotics by Flavoenzyme‐Mediated Sulfur Dioxide Capture. Angewandte Chemie International Edition 2015, 54 (45), 13279-13283.
    16. Wolf, R.; Matz, H.; Orion, E.; Tuzun, B.; Tuzun, Y., Dapsone. Dermatology online journal 2002, 8 (1).
    17. Wozel, G.; Blasum, C., Dapsone in dermatology and beyond. Archives of dermatological research 2014, 306 (2), 103-124.
    18. Cockshott, I. D., Bicalutamide. Clinical pharmacokinetics 2004, 43 (13), 855-878.
    19. McCormack, P. L.; Keating, G. M., Eletriptan. Drugs 2006, 66 (8), 1129-1149.
    20. Lombardo, I.; Ramaswamy, G.; Friedhoff, L.; Asare, E., Intepirdine (RVT-101), a 5-HT6 receptor antagonist, as an adjunct to donepezil in mild-to-moderate Alzheimer's disease: efficacy on activities of daily living domains. The American Journal of Geriatric Psychiatry 2017, 25 (3), S120-S121.
    21. Naganawa, A.; Saito, T.; Nagao, Y.; Egashira, H.; Iwahashi, M.; Kambe, T.; Koketsu, M.; Yamamoto, H.; Kobayashi, M.; Maruyama, T., Discovery of new chemical leads for selective EP1 receptor antagonists. Bioorganic & medicinal chemistry 2006, 14 (16), 5562-5577.
    22. Amarnath, V.; Amarnath, K., Intermediates in the Paal-Knorr synthesis of furans. The Journal of Organic Chemistry 1995, 60 (2), 301-307.
    23. Ghazvini, M.; Shahvelayati, A. S.; Sabri, A.; Nasrabadi, F. Z., Synthesis of furan and dihydrofuran derivatives via Feist–Benary reaction in the presence of ammonium acetate in aqueous ethanol. Chemistry of Heterocyclic Compounds 2016, 52 (3), 161-164.
    24. Li, J. J., Feist–Bénary furan synthesis. In Name Reactions, Springer: 2009; pp 218-219.
    25. Cho, C.-H.; Larock, R. C., Highly substituted lactone/ester-containing furan library by the palladium-catalyzed carbonylation of hydroxyl-substituted 3-iodofurans. ACS combinatorial science 2011, 13 (3), 272-279.
    26. Hosseyni, S.; Su, Y.; Shi, X., Gold catalyzed synthesis of substituted furan by intermolecular cascade reaction of propargyl alcohol and alkyne. Organic letters 2015, 17 (24), 6010-6013.
    27. Mao, S.; Wan, Y.; Peng, H.; Luo, L.; Deng, G., Synthesis of Trifunctionalized Naphtho [1, 2-b] furans Based on the Strategy for the Construction of Both Furan and Naphthalene Cycle. The Journal of organic chemistry 2019, 84 (9), 5261-5270.
    28. Glavač, D.; Gredičak, M., Organocatalytic Asymmetric Transformations of 3-Substituted 3-Hydroxyisoindolinones. Synlett 2017, 28 (08), 889-897.
    29. Shen, J.; You, Q.; Fu, Q.; Kuai, C.; Huang, H.; Zhao, L.; Zhuang, Z., Base-Promoted Cascade C–C Coupling/N-α-sp3C–H Hydroxylation for the Regiospecific Synthesis of 3-Hydroxyisoindolinones. Organic letters 2017, 19 (19), 5170-5173.
    30. Liu, R.; Yang, M.; Xie, W.; Dong, W.; Zhou, H.; Yadav, S.; Potkin, V. I.; Qiu, G., Synthesis of 3-Hydroxyisoindolin-1-ones through 1, 4-Dioxane-Mediated Hydroxylhydrative aza-Cyclization of 2-Alkynylbenzamide in Water. The Journal of organic chemistry 2020, 85 (8), 5312-5320.
    31. Chang, M.-Y.; Cheng, Y.-C.; Lu, Y.-J., Bi (OTf) 3-mediated cycloisomerization of γ-alkynyl arylketones: Application to the synthesis of substituted furans. Organic letters 2015, 17 (5), 1264-1267.
    32. Hsieh, Copper Catalyst for the Synthesis of Various Aryl Amido Furans and Hydroxyisoindolinone Derivatives. 2016.

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