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 |
相關次數: | 點閱:80 下載:0 |
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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.
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.