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研究生:林若竹
研究生(外文):Lin, Jo-Chu
論文名稱:鹵素取代之吲哚[3,2-c]喹啉酮合成研究與過氧化氫於鹼性條件下對含甲基取代之氨基苯甲醯胺之脫胺反應研究
論文名稱(外文):Synthesis of Halogenated Indolo[3,2-c]quinolinones and Deamination of Methylated Aminobenzamide by Hydrogen Peroxide under Alkaline Conditions
指導教授:黃建智黃建智引用關係
指導教授(外文):Huang, Jiann-Jyh
學位類別:碩士
校院名稱:國立嘉義大學
系所名稱:應用化學系研究所
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2019
畢業學年度:108
語文別:中文
論文頁數:67
中文關鍵詞:吲哚[32-c]喹啉酮甲基取代之氨基苯甲醯胺脫胺反應
外文關鍵詞:Indolo[32-c]quinolinonesMethylated AminobenzamideDeamination
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Abstract…………………………………………….…………………..………………I
中文摘要……………………………………………………….……………………..II
誌謝辭………………………………………………………………………………..III
壹、 Synthesis of halogenated indolo[3,2-c]quinolinones…………………………….1
一、前言…………………………………………………..………..………..………..1
1. Indolo[3,2-c]quinolinone之簡介…….…………………..………..……….…...1
2. 銅金屬催化串聯反應用於合成indolo[2,3-c]quinolinones之前期研究成果..2
二、結果與討論………………………………………………………………….….....4
1. 2-(2-Bromophenyl)-N-(2-cyanophenyl)acetamides 8a–h之合成………...…....4
2. 3-Chloro-5,11-dihydro-6H-indolo[3,2-c]quinolin-6-one (9a)之合成探討.........5
3. 含F、Cl、I取代基之5,11-dihydro-6H-indolo[3,2-c]quinolin-6-one合成……...6
三、結論………………………………………………………………..…………..…..7
貳、 Deamination of methylated aminobenzamide by hydrogen peroxide under alkaline conditions..................................................................................................8
一、 前言........................................................................................................................8
1. 回顧deamination反應之發現及2-aminobenzonitrile與2-aminobenzamide之deamination........................................................................................................8
二、 結果與討論..........................................................................................................11
1. 2-(Methylamino)benzamide (16)及2-amino-N-methybenzamide (17)之合成..........................................................................................................................11
2. 2-(Methylamino)benzamide (16)在hydrogen peroxide或urea hydrogen peroxide條件下反應...........................................................................................11
3. 2-Amino-N-methybenzamide (17)在hydrogen peroxide或urea hydrogen peroxide條件下反應...........................................................................................12
4. 1-Methyl-1,2-dihydro-3H-indazol-3-one (21)之結構鑑定............................. 14
5. Deamination之反應機構推測.........................................................................17
三、 結論......................................................................................................................19
參、 Experiment Section……………………………………………....………....…..20
1. Synthesis of halogenated indolo[3,2-c]quinolinones…….…………..……......20
2. Deamination of methylated aminobenzamide by hydrogen peroxide under alkaline conditions …………………………………………………………….....26
肆、 參考文獻……………………………..……………..………………...….……..28
伍、 光譜數據……………..………………………………………..………………..31
Whittell, L. R.; Batty, K. T.; Wong, R. P.M.; Bolitho, E. M.; Fox, S. A.; Davis, T. M.E.; Murray, P. E. Synthesis and Biological Activity of Isocryptolepin. Bioorg. Med. Chem. 2011, 19, 7519–7525.
[2] Primik, M. F.; Göschl, S.; Jakupec, M. A.; Roller, A.; Keppler, B. K.; Arion, V. B. Structure–Activity Relationshpis of Highly Cytotoxic Copper(II) Complexes with Modified Indolo[3,2-c]quinolone Ligands. Inorg. Chem. 2010, 49, 11084–11095.
[3] Chen, Y.-L.; Chung, C.-H.; Chen, I.-L.; Chen, P.-H.; Jeng, H.-Y. Synthesisand cytotoxic activity evaluation of indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones and 6-anilinoindoloquinolin derivatives. Bioorg. Med. Chem. 2002, 10, 2705–2712.
[4] Bergman, J.; Engqvist, R.; Stålhandske, C.; Wallberg, H. Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine. Tetrahedron 2003, 59, 1033–1048.
[5] Hayashi, K.; Choshi, T.; Chikaraishi, K.; Oda, A.; Yoshinaga, R.; Hatae, N.; Ishikura, M.; Hibino, S. Synthesis of isocryptolepine Tetrahedron 2012, 68, 4274–4279.
[6] Li, S.; Ma, S. The first copper-catalyzed cyclic anti-nucleometallation–carboxylation of 2-alkynylanilines. Adv. Synth. Catal. 2012, 354, 2387–2394.
[7] Zhang, X.; Zhang, N. D.; Deng, J.; Du, Y.; Zhao, K. Pd(OAc)2/Cu(OAc)2-mediated oxidative C(sp2)−C(sp2) bond formation and I(III)-mediated oxidative C(sp2 )−N bond formation. J. Org. Chem, 2013, 78, 12750–12759.
[8] Shi, Z.; Ren, Y.; Li, B.; Lu, S.; Zhang, W. CuI-catalyzed photochemical or thermal reactions of 3-(2-azidobenzylidene)- lactams. Chem. Commun. 2010, 46, 3973–3975.
[9] Sawasaki, Y.; Ogata, Y. Mechanism of the Reaction of the Nitriles with Alkaline Hydrogen Peroxide. Bull. Chem. Soc. Jpn. 1981, 54, 793–799.
[10] Mcmaster, L.; Langreck, F. B. The Transformation of Nitriles into Amides by Hydrogen Peroxide. J. Am. Chem. Soc. 1917, 39, 103–109.
[11] Aristoff, P. A.; Johnson, P. D.; Harrison, A. W. Total Synthesis of a Novel Antiulcer Agent via a Modification of the Intramolecular Wadsworth-Emmons-Wittig Reaction. J. Am. Soc. 1985, 107, 7967–7974.
[12] Meth-Cohn, O.; Wang, M. X. 2-aminobenzoic acid from 2-aminobenzonitrile hydrolysis. Tetrahedron Letters 1995, 36, 9561–9564.
[13] Alagiri, K.; Prabhu, K. R. Oxidation ofp-methoxybenzyl azid. Tetrahedron, 2011, 67, 8544–8551.
[14] Guo, Z. J.; Zhou, H. G.; Qu, F. B.; Zhang, W. W.; Guo, L. B. ‘‘Green method for removing hydrazine in oxidizing manner’’ CN 10388062 (A)
[15] Ranganathan, D.; Farooqui, F.; Bhattacharyya, D.; Mehrotra, S.; Kesavan, K. 2-aminobenzoic acid from 2-aminobenzamide hydrolysis. Tetrahedron, 1986, 42, 4481–4492.
[16] Wiberg, K. B. The Mechanisms of Hydrogen Peroxide Reactions. I. The Conversion of Benzonitrile to Benzamide. J. Am. Chem. Soc. 1953, 75, 3961–3946.
[17] Tu, T.; Wang, Z.; Liu, Z.; Feng, X.; Wang, Q. Metal-free catalytic hydration of organonitriles to amides. Green Chem. 2012, 14, 921–924.
[18] Wehle, S.; Espargaró, A.; Sabaté, R.; Decker, M. Sythesis of 2-(methylamino)benzamide. Tetrahedron, 2016, 72, 2535–2543.
[19] Chang, Yaning; Zhang, Jingwei; Chen, Xiulei; Li, Zhong; Xu, Xiaoyong. Cycloaddition of benzo[d][1,2,3]triazin-4(3H)-one from 2-aminobenzamide. Bioorganic and Medicinal Chemistry Letters, 2017, 27, 2641–2644.
[20] Correa, A.; Tellitu, I.; Dominguez, E.; SanMartin, R. Novel Alternative for the N-N Bond Formation through a PIFA-Mediated Oxidative Cyclization and Its Application to the Synthesis of Indazol-3-ones. J. Org. Chem. 2006, 71, 3501–3505.
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