离子液体[C2O2BBTA][TFA]催化合成3,4-二氢嘧啶-2-(1H)-酮/硫酮
Synthesis of 3,4-Dihydropyrimidine-2-(1H)- Ones/Thiones Catalyzed by Ionic Liquid [C2O2BBTA][TFA]
DOI: 10.12677/JOCR.2017.52010, PDF, HTML, XML, 下载: 1,634  浏览: 4,816  国家自然科学基金支持
作者: 张增鹏, 麻 荣, 郭 磊, 刘晨江:石油天然气精细化工教育部&自治区重点实验室,新疆大学理化测试中心,新疆 乌鲁木齐
关键词: 离子液体催化无溶剂34-二氢嘧啶酮-2(1H)-酮/硫酮Ionic Liquids Catalysis Solvent-Free 34-Dihydropyrimidin-2(1H)-Ones/Thiones
摘要: 无溶剂条件下,阳离子为苯并三唑、阴离子为三氟乙酸根的羧基功能化离子液体作为环境友好的催化剂,高效地合成了一系列3,4-二氢嘧啶-2(1H)-酮或硫酮。此外,离子液体[C2O2BBTA][TFA]循环使用至少4次,且催化活性没有明显降低。
Abstract: Carboxyl functional ionic liquid with benzotriazole cation and trifluoroacetate anion can be used as environmental-friendly catalyst for the efficient synthesis of 3,4-dihydropyrimidin-2(1H) ones /thiones under solvent-free conditions. Moreover, the ionic liquid [C2O2BBTA][TFA] can be easily recycled and reused for at least four cycles without obvious loss of catalytic activity.
文章引用:张增鹏, 麻荣, 郭磊, 刘晨江. 离子液体[C2O2BBTA][TFA]催化合成3,4-二氢嘧啶-2-(1H)-酮/硫酮[J]. 有机化学研究, 2017, 5(2): 78-85. https://doi.org/10.12677/JOCR.2017.52010

参考文献

[1] Atwalk, K.S., Rovnyak, G.C., Kimball, S.D., et al. (1990) Dihydropyrimidine Calcium Channel Blockers. II. 3-Sub- stituted-4-Aryl-1,4-Dihydro-6-Methyl-5-Pyrimidinecarboxylic Acid Esters as Potent Mimics of Dihydropyridines. Journal of Medicinal Chemistry, 33, 2629-2635.
https://doi.org/10.1021/jm00171a044
[2] Kappe, C.O. (1993) 100 Years of the Biginelli Dihydropyrimidine Synthesis. Tetrahedron, 49, 6937-6963.
[3] Overman, L.E., Rabinowitz, M.H. and Renhowe, P.A. (1995) Enantioselective Total Synthesis of (-)-Ptilomycalin A. Journal of the American Chemical Society, 117, 2657-2658.
https://doi.org/10.1021/ja00114a034
[4] Snider, B.B., Chen, J., Patil, A.D. and Freyer, A.J. (1996) Synthesis of the Tricyclic Portions of Batzelladines A, B and D. Revision of the Stereochemistry of Batzelladines A and D. Tetrahedron Letters, 37, 6977-6980.
[5] Kappe, C.O., Fabian, W.M.F. and Semones, M.A. (1997) Conformational Analysis of 4-Aryl-Dihydropyrimidine Calcium Channel Modulators. A Comparison of ab Initio, Semiempirical and X-Ray Crystallographic Studies. Tetrahedron, 53, 2803-2816.
[6] Yang, Z.Y. and Guo, H.Y. (2011) One-Pots Synthesis of 3,4-Dihydropyrimidin-2-(1H)-Ones Catalyzed by Acidic Ionic Liquid under Solvent-Free Conditions. Journal of Zhejiang University of Technology, 39, 511-515.
[7] Mayer, T.U., Kapoor, T.M., Haggarty, S.J., et al. (1999) Small Molecule Inhibitor of Mitotic Spindle Bipolarity Identified in a Phenotype-Based Screen. Science, 286, 971-974.
https://doi.org/10.1126/science.286.5441.971
[8] Deres, K., Schröder, C.H., Paessens, A., et al. (2003) Inhibition of Hepatitis B Virus Replication by Drug-Induced Depletion of Nucleocapsids. Science, 299, 893-896.
https://doi.org/10.1126/science.1077215
[9] Li, X., Liu, C, Wang, J. and Li, Y. (2009) Lanthanum Nitrate as an Efficient Catalyst for the Synthesis of 3,4-Dihydro- pyrimidine-2(1H)-(Thio)Ones. Chemistry, 9, 837-840.
[10] Wu, H., Fu, C., Zhao, Y., Yang, B., Wei, Y., Wang, Z. and Tao, L. (2015) Multicomponent Copolycondensates via the Simultaneous Hantzsch and Biginelli Reactions. ACS Macro Letters, 4, 1189-1193.
https://doi.org/10.1021/acsmacrolett.5b00637
[11] Titova, Y., Fedorova, O., Rusinov, G., Vigorov, A., Krasnov, V., Murashkevich, A. and Charushin, V. (2015) Effect of Nanosized TiO2-SiO2 Covalently Modified by Chiral Mole-cules on the Asymmetric Biginelli Reaction. Catalysis Today, 241, 270-274.
[12] Sheykhan, M., Yahyazadeh, A. and Rahemizadeh, Z. (2016) Cu-EDTA-Modified APTMS-Fe3O4@SiO2 Core-Shell Nanocatalyst: A Novel Magnetic Re-coverable Catalyst for the Biginelli Reaction. RSC Advances, 6, 34553-34563.
https://doi.org/10.1039/C6RA02415G
[13] Fedorova, O.V., Titova, Y.A., Vigorov, A.Y., Toporova, M.S., Alisienok, O.A., Murashkevich, A.N., Krasnov, V.P., Rusinov, G.L. and Charushin, V.N. (2016) Asymmetric Biginelli Reaction Catalyzed by Silicon, Titanium and Aluminum Oxides. Catalysis Letters, 146, 493-498.
https://doi.org/10.1007/s10562-015-1666-5
[14] Kefayati, H., Mirfarhadi, S.M. and Kazemi-Rad, R. (2015) Un-expected One-Pot Synthesis of Novel 2-Aminopyrimi- dine-4-Ones under Microwave Irradiation. Journal of the Chemistry Communication, 62, 107-111.
https://doi.org/10.1002/jccs.201400248
[15] Mohammadi, K., Shirini, F. and Yahyazadeh, A. (2015) 1,3-Disulfonic Acid Imidazolium Hydrogen Sulfate: A Reusable and Efficient Ionic Liquid for the One-Pot Mul-ti-Component Synthesis of Pyrimido[4,5-b]Quinoline Derivatives. RSC Advances, 5, 23586-23590.
https://doi.org/10.1039/C5RA02198G
[16] Elhamifar, D., Nasr-Esfahani, M, Karimi, B., Moshkelgosha, R. and Shábani, A. (2016) Ionic Liquid and Sulfonic Acid Based Bifunctional Periodic Mesoporous Organosilica (BPMO-IL-SO3H) as a Highly Efficient and Reusable Nanocatalyst for the Biginelli Reaction. ChemCatChem, 6, 2593-2599.
[17] Zhang, Y.H., Wang, B., Zhang, X.M., Huang, J.B. and Liu, C.J. (2015) An Efficient Synthesis of 3,4-Dihydropyrimi- din-2(1H)-Ones and Thiones Catalyzed by a Novel Brønsted Acidic Ionic Liquid under Solvent-Free Conditions. Molecules, 20, 3811-3820.
https://doi.org/10.3390/molecules20033811
[18] Li, H., Liu, C., Zhang, Y., Sun, Y., Wang, B. and Liu, W. (2015) Green Method for the Synthesis of Chromeno[2,3-c]- Pyrazol-4(1H)-Ones through Ionic Liquid Promoted Directed Annulation of 5-(Aryloxy)-1H-Pyrazole-4-Carbalde- hydes in Aqueous Media. Organic Letters, 17, 932-935.
https://doi.org/10.1021/acs.orglett.5b00033
[19] Xue, F., Ma, R., Sun, Y., Abdukader, A., Zhang, Y. and Liu, C. (2015) Syntheses of Carboxyl Functionalized Benzotriazol-Based Ionic Liquids and Their Application in Extraction-Oxidative Desulfurization. Chemical Journal of Chinese Universities, 36, 1298-1303.
[20] Rao, G.B.D., Acharya, B.N., Verma, S.K. and Kaushik, M.P. (2011) N,N’-Dichlorobis(2,4,6-Trichlorophenyl)Urea (CC-2) as a New Reagent for the Synthesis of Pyrimidone and Pyrimidine Derivatives via Biginelli Reaction. Tetrahedron Letters, 52, 809-812.
[21] Yadav, J.S., Reddy, B.V.S., Sridhar, P., Reddy, J.S.S., Nagaiah, K., Lingaiah, N. and Saiprasad, P.S. (2004) Green Protocol for the Biginelli Three-Component Reaction: Ag3PW12O40 as a Novel, Water-Tolerant Heteropolyacid for the Synthesis of 3,4-Dihydropyrimidinones. European Journal of Organic Chemistry, 2004, 552-557.
https://doi.org/10.1002/ejoc.200300559
[22] Li, W., Zhou, G., Zhang, P., Lai, Y. and Xu, S. (2011) One-Pot Synthesis of Dihydropyrimidiones via Environmentally Friendly Enzyme-Catalyzed Biginelli Reaction. Heterocycles, 83, 2067-2077.
https://doi.org/10.3987/COM-11-12267
[23] Gholap, A.R., Venkatesan, K., Daniel, T., Lahoti, R.J. and Srinivasan, K.V. (2004) Ionic Liquid Promoted Novel and Efficient One Pot Synthesis of 3,4-Dihydropyrimidin-2-(1H)-Ones at Ambient Temperature under Ultrasound Irradiation. Green Chemistry, 6, 147-150.
https://doi.org/10.1039/b314015f
[24] Da Silva, D.L., Fernandes, S.A., Sabino, A.A. and De Fatima, A. (2011) p-Sulfonic Acid Calixarenes as Efficient and Reusable Organocatalysts for the Synthesis of 3,4-Dihydropyrimidin-2(1H)-Ones/-Thiones. Tetrahedron Letters, 52, 6328-6330.
[25] Khabazzadeh, H., Saidi, K. and Sheibani, H. (2008) Microwave-Assisted Synthesis of Dihydropyrimidin-2(1H)-Ones Using Graphite Supported Lanthanum Chloride as a Mild and Efficient Catalyst. Bioorganic & Medicinal Chemistry Letters, 18, 278-280.
[26] Chitra, S. and Pandiarajan, K. (2009) Calcium Fluoride: An Efficient and Reusable Catalyst for the Synthesis of 3,4-Dihydropyrimidin-2(1H)-Ones and Their Corresponding 2(1H)Thione: An Improved High Yielding Protocol for the Biginelli Reaction. Tetrahedron Letters, 50, 2222-2224.