磷钼酸室温催化吲哚与1-乙烯基吡咯烷-2-酮的傅克反应研究
HMA Catalyzed Friedel-Crafts Reaction of Indole and 1-Vinylpyrrolidin-2-One at Ambient Temperature
DOI: 10.12677/JOCR.2019.74014, PDF,    科研立项经费支持
作者: 李建鹏, 张世奇, 高天明, 张永飞, 王 赟, 夏加亮, 韩 冰, 惠永海*：岭南师范学院化学化工学院，清洁能源材料化学广东普通高校重点实验室，广东 湛江
关键词: 杂多酸；吲哚；烯酰胺；傅克反应；Heteropoly Acid； Indole； Enamides； Friedel-Crafts Reaction
摘要: 以杂多酸(磷钼酸和磷钨酸)为催化剂，在水相中对吲哚和1-乙烯基吡咯烷-2-酮进行了Friedel-Crafts反应的催化研究。经过条件筛选，发现在室温下磷钼酸能够更有利于使反应进行，产率可达98%。所有目标产物通过NMR进行了结构表征。该方法具有操作简单和反应条件温和等优点，为碳碳键的形成提供了便捷的方法。
Abstract: Heteropoly acid (HMA and HWA) catalyst was found to be a highly efficient catalyst for the rapid and convenient synthesis of Friedel-Crafts alkylations through indoles and 1-vinylpyrrolidin-2- one in water at room temperature, and the reaction proceeded smoothly with good results under the catalysis of HMA (up to 98% yield). All the corresponding products were characterized by NMR. The approach exhibits the advantages of simple operation and mild reaction conditions, which provides a convenient method for the formation of carbon-carbon band in organic synthesis.
文章引用：李建鹏, 张世奇, 高天明, 张永飞, 王赟, 夏加亮, 韩冰, 惠永海. 磷钼酸室温催化吲哚与1-乙烯基吡咯烷-2-酮的傅克反应研究[J]. 有机化学研究, 2019, 7(4): 103-108. https://doi.org/10.12677/JOCR.2019.74014

参考文献

[1] Enthaler, S. and Wu, X.F. (2015) Zinc Catalysis Applications in Organic Synthesis: Part 4. Wiley-VCH Verlag GmbH & Co. KGaA, Hoboken, 57-82. [Google Scholar] [CrossRef] 
[2] Shiri, M. (2012) Indoles in Multi-component Processes (MCPs). Chemical Reviews, 112, 3508-3549. [Google Scholar] [CrossRef] [PubMed]
[3] Brogi, S., Campiani, G., Brindisi, M. and Butini, S. (2019) Allosteric Modulation of Ionotropic Glutamate Receptors: An Outlook on New Therapeutic Approaches to Treat Central Nervous System Disorders. ACS Medicinal Chemistry Letters, 10, 228-236. [Google Scholar] [CrossRef] [PubMed]
[4] Stout, K.A., Dunn, A.R., Hoffman, C. and Miller, G.W. (2019) The Synaptic Vesicle Glycoprotein 2: Structure, Function, and Disease Relevance. ACS Chemical Neuroscience, 10, 3927-3938. [Google Scholar] [CrossRef] [PubMed]
[5] Buol, X., Robeyns, K., Tumanov, N., Wouters, J. and Leyssens, T. (2019) Identifying, Characterizing, and Understanding Nefiracetam in Its Solid State Forms: A Potential Antidementia Drug. Jouranl of Pharmaceutical Sciences, 108, 3616-3622. [Google Scholar] [CrossRef] [PubMed]
[6] Kingsberg, S.A., McElroy, S.L. and Clayton, A.H. (2019) Evaluation of Flibanserin Safety: Comparison with Other Serotonergic Medications. Sexual Medicine Reviews, 7, 380-392. [Google Scholar] [CrossRef] [PubMed]
[7] Bychkov, I., Kudryakova, N., Andreeva, A., Pojidaeva, E. and Kusnetsov, V. (2019) Melatonin Modifies the Expression of the Genes for Nuclear- and Plastid-Encoded Chlo-roplast Proteins in Detached Arabidopsis Leaves Exposed to Photooxidative Stress. Plant Physiology and Biochemistry, 144, 404-412. [Google Scholar] [CrossRef] [PubMed]
[8] Jiang, R., Xu, H.Y., Xu, X.P., Chu, X.Q. and Ji, S.J. (2011) Direct Alkylation of Indoles and Amines by tert-Enamides: Facile Access to Pharmaceutically Active 2-Oxo-1-Pyrrolidine Analogues. Organic & Biomolecular Chemistry, 9, 5659-5669. [Google Scholar] [CrossRef] [PubMed]
[9] Niu, T.M., Huang, L.H., Wu, T.X. and Zhang, Y.H. (2011) FeCl3-Promoted Alkylation of Indoles by Enamides. Organic & Biomolecular Chemistry, 9, 273-277. [Google Scholar] [CrossRef] 
[10] Jiang, R., Wu, X.J., Zhu, X., Xu, X.P. and Ji, S.J. (2010) Ferric(III) Nitrate: An Efficient Catalyst for the Regioselective Friedel-Crafts Reactions of Indoles and tert-Enamides in Water. European Journal of Organic Chemistry, 31, 5946-5950. [Google Scholar] [CrossRef] 
[11] Li, L.J., Jiang, Y.Y., Lam, C.M., Zeng, C.C., Hu, L.M. and Little, R.D. (2015) Aromatic C-H Bond Functionalization Induced by Electrochemically in Situ Generated tris(p-bromophenyl) Aminium Radical Cation: Cationic Chain Reactions of Electron-Rich Aromatics with Enamides. The Journal of Organic Chemistry, 80, 11021-11030. [Google Scholar] [CrossRef] [PubMed]
[12] Huo, C.D., Kang, L.S., Xu, X.L., Jia, X.D., Wang, X.C., Xie, H.S. and Yuan, Y. (2014) Triarylaminium Salt Facilitated Friedel-Crafts Reaction of Indoles with Enamides and Vinyl Ethers. Tetrahedron Letters, 55, 954-958. [Google Scholar] [CrossRef] 
[13] Jia, Y.X., Zhong, J., Zhu, S.F., Zhang, C.M. and Zhou, Q.L. (2007) Chiral Brønsted Acid Catalyzed Enantioselective Friedel-Crafts Reaction of Indoles and α-aryl Enamides: Construction of Quaternary Carbon Atoms. Angewandte Chemie International Edition, 46, 5565-5567. [Google Scholar] [CrossRef] [PubMed]
[14] Zhang, Y., Jiang, J., Chu, X.Q., Jiang, R., Xu, X.P., Li, D.H. and Ji, S.J. (2012) Friedel-Crafts Alkylation of Indoles by tert-Enamides in Acetic Acid. Synlett, 23, 751-754. [Google Scholar] [CrossRef] 
[15] Xu, H.Y., Zi, Y., Xu, X.P., Wang, S.Y. and Ji, S.J. (2013) TFA-Catalyzed C-N Bond Activation of Enamides with Indoles: Efficient Synthesis of 3,3-Bisindolylpropanoates and Other Bisindolylalkanes. Tetrahedron, 69, 1600-1605. [Google Scholar] [CrossRef] 
[16] Xing, L.Z., Yang, J.H., Xing, X.J., Hou, Y.D., Wu, Y. and Hui, Y.H. (2018) MCM-41-Accelerated PWA Catalysis of Friedel-Crafts Reaction of Indoles and Isatins. Journal of Chemistry, 2018, Article ID: 2785067. [Google Scholar] [CrossRef] 
[17] 惠永海, 石伟, 谢绍雷, 王长春, 解正峰. 水溶液中介孔分子筛MCM-41负载磷钨酸(PW)催化三组分Mannich反应研究[J]. 有机化学, 2014, 34(6): 1212-1217.
[18] Fan, K., Hui, Y.H., Hu, X.M., Shi, W., Pang, H.X. and Xie, Z.F. (2015) PMoA/MCM-41 Catalyzed Aza-Michael Reaction: Special Effects of Mesoporous Nanoreactor on Chemical Equilibrium and Reaction Rate through Surface Energy Transformation. New Journal of Chemistry, 39, 5916-5919. [Google Scholar] [CrossRef] 
[19] 侯亚东, 董秀芝, 杨超, 惠永海, 解正峰. MCM-41负载杂多酸水相中催化亚胺和丙二腈的加成-消去反应[J]. 有机化学, 2018, 38(7): 197-202.

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