介孔分子筛MCM-41固载磷钨酸催化苯并三氮唑与查尔酮的氮杂迈克加成反应研究
Aza-Michael Addition of Chalcone with Benzotriazole Catalyzed by MCM-41 Immobilized H3PW12O40
DOI: 10.12677/JOCR.2017.52014, PDF, HTML, XML, 下载: 1,749  浏览: 4,509  国家自然科学基金支持
作者: 杨敬辉, 邢刘庄, 谢绍雷, 邢雪建, 侯亚东, 吴 阳, 惠永海：新疆大学化学化工学院，新疆 乌鲁木齐
关键词: MCM-41；磷钨酸；苯并三氮唑；查尔酮；迈克加成；MCM-41； Phosphoric Acid； Benzotriazole； Chalcone； Michael Addition
摘要: 以介孔分子筛MCM-41固载磷钨酸为催化剂，对苯并三氮唑与查尔酮进行了氮杂迈克加成的催化研究。经过条件筛选，发现MCM-41中的磷钨酸负载量对该反应体系有很大的影响，其中50 wt%的磷钨酸负载量更有利于反应的进行，产率可达98%。通过NMR对产物结构进行了表征，并且催化剂具有一定的回收再利用效果。
Abstract: In this paper, mesoporous siliceous material MCM-41 supported H3PW12O40 (PW) could act as an efficient catalyst for the aza-Michael addition reaction of chalcone with benzotriazole. As can be seen from a serial of reaction conditions, the ratio of PW and MCM-41 plays a critical role in the reaction, and the best catalyzed result was achieved when using 50 wt% PW/MCM-41, and the yield was up to 98%. All the products were confirmed by NMR techniques. Moreover, the catalyst was also found to exhibit better recyclability.
文章引用：杨敬辉, 邢刘庄, 谢绍雷, 邢雪建, 侯亚东, 吴阳, 惠永海. 介孔分子筛MCM-41固载磷钨酸催化苯并三氮唑与查尔酮的氮杂迈克加成反应研究[J]. 有机化学研究, 2017, 5(2): 107-113. https://doi.org/10.12677/JOCR.2017.52014

参考文献

[1] Carta, A., Palomba, M., Boatto, G., Busonera, B., Murreddu, M. and Loddo, R. (2004) Synthesis and Antiproliferative Activity of 3-aryl-2-[1H(2H)-benzotriazol-1(2)-yl]acrylonitriles Variously Substituted: Part 4. IL Farmaco, 59, 637- 644.
[2] Carta, A., Palomba, M., Paglietti, G., Molicotti, P. and Paglietti, B.(2007) [1,2,3]Triazolo[4,5-h]quinolones. A New Class of Potent Antitubercular Agents against Multidrug Resistant Mycobacterium Tuberculosis Strains. Bioorganic & Medicinal Chemistry Letters, 17, 4791-4794.
[3] Lakshman, M.K., Singh, M.K., Kumar, M., Chamala, R.R., Yedulla, V.R., Wagner, D., Leung, E., Yang, L.J., Matin, A. and Ahmad, S. (2014) Facile Synthesis of 1-alkoxy-1H-benzo- and 7-azabenzotriazoles from Peptide Coupling Agents, Mechanistic Studies, and Synthetic Ap-plications. Beilstein Journal of Organic Chemistry, 10, 1919-1932.
https://doi.org/10.3762/bjoc.10.200
[4] Wang, J., Wang, W.T., Liu, X.H., Hou, Z.R., Lin, L.L. and Feng, X.M. (2011) Highly Enantioselective Direct Michael Addition of 1H-Benzotriazole to Chalcones Catalyzed by Sc(OTf)3/N,N′-Dioxide Complex. European Journal of Organic Chemistry, 11, 2039.
https://doi.org/10.1002/ejoc.201100021
[5] Vanderwal, C.D. and Jacobsen, E.N. (2004) Enantioselective Formal Hydration of α,β-Unsaturated Imides by Al-Catalyzed Conjugate Addition of Oxime Nucleophiles. Jouranl of the American Chemical Society, 126, 14724.
https://doi.org/10.1021/ja045563f
[6] Uria, U., Vicario, J.L., Badia, D. and Carrillo, L. (2007) Organocatalytic Enantioselective Aza-Michael Reaction of Nitrogen Heterocycles and α,β-Unsaturated Aldehydes. Chemical Commu-nication, 24, 2509.
https://doi.org/10.1039/B700831G
[7] Hua, Q.L., Li, C., Wang, X.F., Lu, L.Q., Chen, J.R. and Xiao, W.J. (2011) Enantioselective Synthesis of Chromans with a Quaternary Stereogenic Centre through Catalytic Asymmetric Cascade Reactions. ACS Catalysis, 1, 221.
https://doi.org/10.1021/cs100161k
[8] Cai, Q., Zheng, C., Zhang, J.W. and You, S.L. (2010) Enantioselective Intramolecular Aza-Michael Additions of Indoles Catalyzed by Chiral Phosphoric Acids. Angewandte Chemmie Inter-national Edition, 49, 8666.
https://doi.org/10.1002/anie.201003919
[9] Mokhtar, M., Saleh, T.S. and Basahel, S.N. (2012) Mg-Al hy-drotalcites as Efficient Catalysts for Aza-Michael Addition Reaction: A Green Protocol. Journal of Molecular Catalysis A: Chemical, 353-354, 122.
[10] Dong, X.Z., Hui, Y.H., Xie, S.L., Zhang, P., Zhou, G.P. and Xie, Z.F. (2013) Schiff Base Supported MCM-41 Catalyzed the Knoevenagel Condensation in Water. RSC Advances, 3, 3222.
https://doi.org/10.1039/c3ra00138e
[11] 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.
[12] Kui, F., 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.
https://doi.org/10.1039/C5NJ01507C
[13] 邢雪建, 樊馗, 庞海霞, 吴阳, 杨敬辉, 石伟, 解正峰, 惠永海. 介孔分子筛MCM-41 固载席夫碱与醋酸锌共催化“一锅法”合成噻唑啉酮衍生物[J]. 有机化学, 2016, 36(8): 1942.
[14] 朱庆英, 沈海民, 纪红兵. β-环糊精衍生物诱导H2O2水相不对称环氧化trans-查尔酮[J]. 有机化学, 2016, 36(8): 1907.

为你推荐