磷钨酸促进的酰肼与查尔酮缩合反应的研究
Study on the Condensation Reaction of Hydrazide with Benzylideneacetophenone Catalyzed by Phosphotungstic Acid
DOI: 10.12677/JOCR.2016.44013, PDF,    国家自然科学基金支持
作者: 吴 阳, 邢雪建, 邢刘桩, 侯亚东, 杨敬辉, 惠永海：新疆大学化学化工学院，新疆 乌鲁木齐
关键词: 杂多酸；缩合反应；酰腙；Heteropoly Acid； Condensation Reaction； Acylhydrazone
摘要: 本文以杂多酸–磷钨酸为催化剂，对酰肼与查尔酮的缩合反应进行了研究。经过一系列反应条件的筛选，确立了最佳反应条件，并对底物的普适性进行了考察，得到了一系列高产率的酰腙类目标产物，最高产率达到99%。本反应操作简单，条件温和，为查尔酮酰腙合成提供了一种新的方法。
Abstract: The condensation of hydrazide with benzylideneacetophenone was studied by using phospho-tungstic acid as catalyst. After a series of reaction conditions, the optimal reaction conditions were established, and the universality of the substrate was investigated. A series of acylhydrazones were obtained with the high yields, up to 99%. The reaction was simple and mild, which provided a new method for the synthesis of chalcone hydrazone.
文章引用：吴阳, 邢雪建, 邢刘桩, 侯亚东, 杨敬辉, 惠永海. 磷钨酸促进的酰肼与查尔酮缩合反应的研究[J]. 有机化学研究, 2016, 4(4): 93-99. https://dx.doi.org/10.12677/JOCR.2016.44013

参考文献

[1] Rollas, S. and Küçükgüzel, S.G. (2007) Biological Activities of Hydrazone Derivatives. Molecules, 12, 1910-1939. [Google Scholar] [CrossRef] [PubMed]
[2] Vicini, P., Zani, F., Cozzini, P. and Doytchinova, I. (2002) Hydrazones of 1, 2-Benzisothiazole Hydrazides: Synthesis, Antimicrobial Activity and QSAR Investigations. European Journal of Medicinal Chemistry, 37, 553-564. [Google Scholar] [CrossRef] 
[3] Jayabharathi, J., Thangamani, A., Padmavathy, M. and Krishnakumar, B. (2007) Synthesis and Microbial Evaluation of Novel n (1)-arilidene-n (2)-t (3)-methyl-r(2), c (6)-diaryl-piperidin-4-one Azine Derivatives. Medicinal Chemistry Research, 15, 431-442. [Google Scholar] [CrossRef] 
[4] Ragavendran, J.V., Sriram, D., Patel, S.K., Reddy, I.V., Bharathwajan, N. and Stables, J. (2007) Design and Synthesis of Anticonvulsants from a Combined Phthalimide-Gaba-Anilide and Hydrazone Pharmacophore. European Journal of Medicinal Chemistry, 42, 146-151. [Google Scholar] [CrossRef] [PubMed]
[5] El-Hawash, S.A.M., Wahab, A.E.A. and El-Demellawy, M.A. (2006) Cyanoacetic Acid Hydrazones of 3-(and 4-)acetylpyridine and Some Derived Ring Systems as Potential Antitumor and Anti-HCV Agents. Archiv Der Pharmazie, 339, 14-23. [Google Scholar] [CrossRef] [PubMed]
[6] Todeschini, A.R., Miranda, A.L.P.D., Silva, K.C.M.D., Parrini, S.C. and Barreiro, E.J. (1998) Synthesis and Evaluation of Analgesic, Antiinflammatory and Antiplatelet Properties of New 2-Pyridylarylhydrazone Derivatives. European Journal of Medicinal Chemistry, 33, 189-199. [Google Scholar] [CrossRef] 
[7] Nath, M., Vats, M. and Roy, P. (2013) Tri- and Diorganotin(iv) Complexes of Biologically Important Orotic Acid: Synthesis, Spectroscopic Studies, In Vitro Anti-Cancer, DNA Fragmentation, Enzyme Assays and In Vivo Anti-Inflammatory Activities. European Journal of Medicinal Chemistry, 59, 310-321. [Google Scholar] [CrossRef] [PubMed]
[8] Despaigne, A.A.R., Costa, F.B.D., Piro, O.E., Castellano, E.E., Louro, S.R.W. and Beraldo, H. (2012) Complexation of 2-Acetylpyridine- and 2-Benzoylpyridine-Derived Hydrazones to Copper (ii) as an Effective Strategy for Antimicrobial Activity Improvement. Polyhedron, 38, 285-290. [Google Scholar] [CrossRef] 
[9] Xu, Z.H., Zhang, X.W., Zhang, W.Q., Gao, Y.H. and Zeng, Z.Z. (2011) Synthesis, Characterization, DNA Interaction and Antibacterial Activities of Two Tetranuclear Cobalt (ii) and Nickel (ii) Complexes with Salicylaldehyde 2-Phenylquinoline-4-Carboylhydrazone. Inorganic Chemistry Communications, 14, 1569-1573. [Google Scholar] [CrossRef] 
[10] El-Sayed, L., Iskander, M.F., Hawash, N.M. and Massoud, S.S. (1998) Synthesis and Characterization of Nickel(ii), Zinc(ii), Copper(ii), Cobalt(ii) and Cobalt(iii) complexes of α-Dicarbonylbis(aroylhydrazone). Polyhedron, 17, 199-206. [Google Scholar] [CrossRef] 
[11] Lal, R.A., Adhikari, S., Pal, A., Siva, A.N. and Ku-mar, A. (1997) Synthesis and Characterization of the Homobimetallic [bis(2-hydroxy-1-naphthaldehyde)oxaloyldihydrazonato]bis(dioxomolybdenum(vi)) Tetrahydrate Complex and Its Reactivity towards Proton and Electron Donor Reagents. Journal of Chemical Research, 4, 122-123. [Google Scholar] [CrossRef] 
[12] Aboraia, A.S., Yee, S.W., Gomaa, M.S., Shah, N., Robotham, A.C. and Makowski, B. (2010) Synthesis and CYP24AL Inhibitory Activity of N-(2-(1H-imidazol-1-yl)-2-phenylethyl)arylamides. Bioorganic & Medicinal Chemistry, 18, 4939-4946. [Google Scholar] [CrossRef] [PubMed]
[13] Fatmawati, S., Kondo, R. and Shimizu, K. (2013) Structure-Activity Relationships of Lanostane-Type Triterpenoids from Ganoderma Lingzhi, as α-Glucosidase Inhibitors. Bioorganic & Medicinal Chemistry Letters, 23, 5900-5903. [Google Scholar] [CrossRef] [PubMed]
[14] Ma, J., Shi, W., Feng, L., Chen, Y., Fan, K. and Hao, Y. (2016) A Highly Selective and Sensitive Acylhydrazone- Based Turn-On optical Sensor for Al3+. RSC Advances, 6, 28034-28037. [Google Scholar] [CrossRef] 
[15] Hu, J.H., Li, J.B., Qi, J. and Sun, Y. (2015) Acylhydrazone Based Fluorescent Chemosensor for Zinc in Aqueous Solution with High Selectivity and Sensitivity. Sensors & Actuators B Chemical, 208, 581-587. [Google Scholar] [CrossRef] 
[16] 李在国, 王清民, 黄君珉. 有机中间体制备[M]. 第二版. 北京: 化学工业出版社, 1996: 51.

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