多取代吡喃[2,3-c]吡唑类化合物的在离子液体[Bmim]BF4催化下的四组分一锅法合成
One-Pot Four-Component Synthesis of Multi-Substituted Pyrano[2,3-c] Pyrazole under Ionic Liquid [Bmim]BF4 Catalysis
摘要: 本文报道了在离子液体[Bmim]BF4催化下以丙酰乙酸甲酯或丙酰乙酸乙酯,苯肼,芳醛和丙二腈等四组分为原料经过一锅法合成了一系列多取代吡喃[2,3-c]吡唑类化合物的方法。该方法具有方便,产率较高等特点,为合成此类化合物提供了一个参考依据。产物的结构通过IR,1H NMR和MS进行表征。
Abstract: A series of multi-substituted pyrano[2,3-c]pyrazole derivatives were synthesized by one-pot reac-tion of ethyl propionyl acetate, phenylhydrazine, aromatic aldehyde and malononitrile. We developed an efficient and convenient method for the synthesis of multi-substituted pyrano[2,3-c]pyrazoles in high yields using ionic liquid [Bmim]BF4 as a catalyst. And structures of the products were characterized by IR, 1H NMR and MS.
文章引用:阿地里江•吾买尔江, 李文博, 夏依努尔•艾力, 梁杰. 多取代吡喃[2,3-c]吡唑类化合物的在离子液体[Bmim]BF4催化下的四组分一锅法合成[J]. 有机化学研究, 2016, 4(2): 51-55. http://dx.doi.org/10.12677/JOCR.2016.42007

参考文献

[1] Vijay, N., Rajesh, C., Vinod, A.U., et al. (2004) Strategies for Heterocyclic Construction via Novel Multicomponent Reactions Based on Isocyanides and Nucleophilic Carbenes. Accounts of Chemical Research, 36, 899-907.
[2] Bruce, G. (2009) Strategies for Innovation in Multicomponent Reaction Design. Accounts of Chemical Research, 42, 463-472.
http://dx.doi.org/10.1021/ar800214s
[3] Dömling, A. and Ugi, I. (2000) Multicomponent Reactions with Isocyanides. Angewandte Chemie International Edition, 39, 3168-3210.
http://dx.doi.org/10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U
[4] David, T. and Fernando, G.T. (2007) Chemo-Differentiating ABB’ Multicomponent Reactions. Privileged Building Blocks. Chemical Society Reviews, 36, 484-491.
http://dx.doi.org/10.1039/B608164A
[5] Pirrung, M.C. and Koushik Das, S. (2004) Multicomponent Reactions Are Accelerated in Water. Journal of the American Chemical Society, 126, 444-445.
http://dx.doi.org/10.1021/ja038583a
[6] Kuo, S.C., Huang, L.J. and Nakamura, H. (1984) Studies on Heterocyclic Compounds. 6. Synthesis and Analgesic and Antiinflammatory Activities of 3,4-Dimethylpyrano[2,3-c]pyrazol-6-one Derivatives. Journal of Medicinal Chemistry, 27, 539-544.
http://dx.doi.org/10.1021/jm00370a020
[7] Ravindernath, A., Reddy, M.S. and Sunil, V. (2014) Synthesis and Biological Evaluation of Benzo[d]imidazolyl chromeno [2,3-d]pyrimidinones. Medicinal Chemistry Research, 23, 759-764.
http://dx.doi.org/10.1007/s00044-013-0674-5
[8] Mandha, S.R., Siliveri, S., Alla, M., Bommena, V.R., Bommineni, M.R. and Balasubramanian, S. (2012) ChemInform Abstract: Eco-Friendly Synthesis and Biological Evaluation of Substituted Pyrano[2,3-c]pyrazoles. Bioorganic & Medicinal Chemistry Letters, 43, 5272-5278.
http://dx.doi.org/10.1016/j.bmcl.2012.06.055
[9] Mandour, A.H., Elsawy, E.R., Ebaid, M.S., et al. (2012) Synthesis and Potential Biological Activity of Some Novel 3-[(N-substituted indol-3-yl)methyleneamino]-6-amino-4-aryl-pyrano(2,3-c)pyrazole-5-carbonitriles and 3,6-diamino- 4-(N-substituted indol-3-yl)pyrano(2,3-c)pyrazole-5-carbonitriles. Acta Pharmaceutica, 62, 15-30.
http://dx.doi.org/10.2478/v10007-012-0007-0