取代邻溴苯乙炔的合成及其在取代吲哚啉合成中的应用研究
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摘要
论文在广泛查阅国内外文献资料的基础上,对取代邻溴苯乙炔的应用合成以及吲哚啉类化合物的应用和合成进行了综合评述,成功地发展了一种以取代邻溴苯乙烯为原料经过两步反应合成相应的取代邻溴苯乙炔的新方法,并发展了一种以取代邻溴苯乙炔为原料在碘化亚铜催化下一锅法合成取代吲哚啉的多组分反应。
以取代的邻溴苯乙烯为原料,在室温下以四氯化碳为反应溶剂与单质溴反应定量地得到加成产物,该加成产物在室温下以无水四氢呋喃为溶剂与三当量的叔丁醇钾反应,高产率地得到相应的邻溴苯乙炔。该方法具有原料易得、条件温和、操作简便和产率较高等优点。
以碘化亚铜为催化剂,邻溴苯乙炔、磺酰叠氮和伯胺在室温下发生三组分反应,所生成的中间体继而加入催化量的碘化亚铜和脯氨酸及两当量的碳酸钾,加热至60℃反应两小时后,即得目标产物取代的吲哚啉。该方法具有适用性好,反应条件温和及分子收敛性好等优点。
The thesis has made collective reviews on the application and synthetic methods of substituted o-bromophenylacetylenes,as well as the application and synthetic methods of indolines, which were based on the comprehensive study of related domestic and abroad articles. A novel two-step synthesis of substituted o-bromophenylacetylenes from o-bromostyrenes has been successfully developed. Catalyzed by iodide copper, substituted indolines could be abtained from o-bromophenyl- acetylenes participated one-pot multicomponent reactions.
Used as raw materials, substituted o-bromostyrenes treated with bromine could quantitively afford corresponding addition products in CCl4 solvent at room temperature. Substituted o-bromophenyl- acteylenes could be abtained in high yields when the addition products were treated with three equivalents of potassium tert-butoxide in dry THF at room temperature. Our procedure has some advantages, such as readily available raw materials, mild reaction condition, ease of operation, and high yields.
Catalyzed by iodide copper, the three-component reactions of o-bromophenylacteylenes, sulfonyl azides, and primary amines readily occurred. To the reaction solution were then added iodide copper, L-proline, and two equivalents of potassium carbonate. The substituted indoline products could be abtained after the mixtures were stired under 60℃under N2 for 2 h. Our procedure has some advantages, such as reaction generality, mild reaction condition, and high convergency.
以取代的邻溴苯乙烯为原料,在室温下以四氯化碳为反应溶剂与单质溴反应定量地得到加成产物,该加成产物在室温下以无水四氢呋喃为溶剂与三当量的叔丁醇钾反应,高产率地得到相应的邻溴苯乙炔。该方法具有原料易得、条件温和、操作简便和产率较高等优点。
以碘化亚铜为催化剂,邻溴苯乙炔、磺酰叠氮和伯胺在室温下发生三组分反应,所生成的中间体继而加入催化量的碘化亚铜和脯氨酸及两当量的碳酸钾,加热至60℃反应两小时后,即得目标产物取代的吲哚啉。该方法具有适用性好,反应条件温和及分子收敛性好等优点。
The thesis has made collective reviews on the application and synthetic methods of substituted o-bromophenylacetylenes,as well as the application and synthetic methods of indolines, which were based on the comprehensive study of related domestic and abroad articles. A novel two-step synthesis of substituted o-bromophenylacetylenes from o-bromostyrenes has been successfully developed. Catalyzed by iodide copper, substituted indolines could be abtained from o-bromophenyl- acetylenes participated one-pot multicomponent reactions.
Used as raw materials, substituted o-bromostyrenes treated with bromine could quantitively afford corresponding addition products in CCl4 solvent at room temperature. Substituted o-bromophenyl- acteylenes could be abtained in high yields when the addition products were treated with three equivalents of potassium tert-butoxide in dry THF at room temperature. Our procedure has some advantages, such as readily available raw materials, mild reaction condition, ease of operation, and high yields.
Catalyzed by iodide copper, the three-component reactions of o-bromophenylacteylenes, sulfonyl azides, and primary amines readily occurred. To the reaction solution were then added iodide copper, L-proline, and two equivalents of potassium carbonate. The substituted indoline products could be abtained after the mixtures were stired under 60℃under N2 for 2 h. Our procedure has some advantages, such as reaction generality, mild reaction condition, and high convergency.
引文
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[13] Zhang Wen-xiong, Nishiura M, Hou Zhao-min. Synthesis of (Z)-1-aza-1,3- -enynes by the cross-coupling of terminal alkynes with isocyanides catalyzed by rare-earth metal complexes [J]. Angew. Chem. Int. Ed. 2008, 47, 9700–9703.
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[15] Manolikakes G, Hernandez C M, Schade M A. Palladium and nickel catalyzed cross-couplings of unsaturated halides bearing relatively acidic protons with organozinc reagents [J]. J. Org. Chem. 2008, 73, 8422– 8436.
[16] Sanji T, Shiraishi K, Kashiwabara T, et al. Base-mediated cyclization reaction of 2-alkynyl-phenylphosphine oxides: Synthesis and photophysical properties of benzo[b]phosphole oxides [J]. Org. Lett. 2008, 10, 2689-2692.
[17] Kim J, Lee S Y, LEE J. et al. Synthetic utility of ammonium salts in a Cu-catalyzed three-component reaction as a facile coupling partner [J]. J. Org. Chem. 2008, 73, 9454–9457.
[18] Mao G L , Orita A , Matsuo D, et al. Synthesis and spectroscopic study of silacyclyne-substituted phenyleneethynylenes [J]. Tetrahedron Lett. 2009. 50, 2860–2864.
[19]刘林.苯乙炔衍生物的合成[J].四川化工. 1995, 4, 2-6.
[20] Gavrilov L D, et al. J. Chem. Soc. 1979, 478-480; Masakatsu M, Keiko K. A convenient synthesis of 1-bromoolefins and acetylenes by a chain extension of aldehydes [J]. Tetrahedron Lett. 1980, 21, 4021-4024.
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[23] Kurihara T, Ebisawa F, Tabei H [P]. Jpn. Kokai Tokkyo Koho. JP 60217213 [85,217,213], 30 Oct 1985.
[24] Masakazu N. Synthesis and polymerization of 2,5-disubstituted phenylacetylenes containing trifluoromethyl groups [J]. J. Fluorine Chem. 1989, 43(1), 35-51.
[25] Kazuo Kodaira, Kunio Okuhara. Preparation of Fluorine-Containing Phenyl- acetylenes by the Method of Introduction of the Ethynyl Group Using 1,1-Dichloro-2,2-difluoroethene [J]. Bull. Chem. Soc. Jpn. 1988, 61(5), 1625-1631.
[26] Alabugin I V, Gilmore K, Patil S, et al. Radical cascade transformations of tris(o-aryleneethynylenes) into substituted benzo[a]indeno[2,1-c]fluorenes [J]. J. Am. Chem. Soc. 2008, 130, 11535– 11545.
[27] Ghaffarzadeh M, Bolourtchian M, Fard Z H. One-step synthesis of aromatic terminal alkynes from their corresponding ketones under microwave irradiation [J]. Synth. Commun. 2006, 36, 1973– 1981.
[28] Quesada E, Raw S A, Reid M, et al. One-pot conversion of activated alcohols into 1,1-dibromoalkenes and terminal alkynes using tandem oxidation processes with manganese dioxide [J]. Tetrahedron 2006, 62, 6673–6680.
[29] Chidester C G, Krueger W C, Mizsak S A. et al. The structure of CC-1065, a potent antitumor agent and its binding to DNA [J]. J. Am. Chem. Soc. 1981, 103, 7629-7635.
[30] Li L H, Swenson D H, Schpok S L F, et al. CC-1065 (NSC 298223), a Novel Antitumor Agent That Interacts Strongly with Double-stranded DNA [J]. Cancer Res. 1982, 42, 999-1004.
[31] Bhuyan B K, Newell K A, Crampton S L, Von Hoff D D. CC-1065 (NSC 298223), a Most Potent Antitumor Agent: Kinetics of Inhibition of Growth, DNA Synthesis, and Cell Survival [J]. Cancer Res. 1982, 42, 3532-3537.
[32] Xiao Z, Hao Y, Liu B, et al. Indirubin and Meisoindigo in the Treatment of Chronic Myelogenous Leukemia in China [J]. Leuk Lymphoma, 2002, 43, 1763 -1768.
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