Study on the Use of the Ionic Liquid 1-butyl-3-methylimidazolium Hydroxide in Synthesis of Substituted 4-aryl-4H-chromenes
Main Article Content
Abstract
Abstracts: An efficient and simple synthesis of substituted 2-amino-4H-chromene-3-carbonitriles was developed by the one-pot and three-component reaction of a mixture of corresponding substituted benzaldehydes, resorcinol, and malononitrile in the presence of an ionic liquid, namely 1-butyl-3-methylimidazolium hydroxide, as catalyst at room temperature. The structure of synthesized compounds have been confirmed by using spectroscopic methods (IR, 1H and 13C NMR).
Keywords: Ionic liquid, chromenes, pyrans, one-pot reaction, three-component reaction.
References
References
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[5] Keerthy H.K., Garg M., Mohan C.D., Madan V., Kanojia D., Shobith R., Nanjundaswamy S., Mason D.J., Bender A., Basappa, Rangappa K.S., Koeffler H.P. (2014), “Synthesis and Characterization of Novel 2-Amino-Chromene-Nitriles that Target Bcl-2 in Acute Myeloid Leukemia Cell Lines”, PLoS One, 9, 107–118.
[6] Javanshir Sh., Safari M. and Dekamin M.G. (2014), “A facile and green three-component synthesis of 2-amino-3-cyano-7-hydroxy-4H-chromenes on grinding”, Scientia Iranica C 21(3), 742-747.
[7] Behbahani F.K. and Mehraban S. (2015), “Synthesis of 2-Amino-3-cyano-7-hydroxy-4H-chromenes Using L-Proline as a Biocatalyst”, Journal of the Korean Chemical Society, 59(4), 284-288.
[8] Safari J., Zarnegar Z., Heydarian M. (2012), “Magnetic Fe3O4 Nanoparticles as Efficient and Reusable Catalyst for the Green Synthesis of 2-Amino-4H-chromene in Aqueous Media”, Bulletin of the Chemical Society of Japan, 85(12), 1332-1338.
[1] Azizian J., Delbari A. S., Yadollahzadeh K. (2014), “One-Pot, Three-Component Synthesis of Pyrimido[4,5-b]quinoline-tetraone Derivatives in Water”, Synthic Communication, 44, 3277-3286.
[2] Nguyen Dinh Thanh, Le The Hoai, Nguyen Thi Kim Giang, Nguyen Van Quoc (2016), “Synthesis of Some Aromatic Peracetylated N-(β-D-Glucopyranosyl)Thiosemicarbazones”, Current Organic Synthesis, 13 (2016, in press).
[3] Vosooghi M., Rajabalian S., Sorkhi M., Badinloo, M., Nakhjiri, M., Negahbani, A. S., Asadipour A., Mahdavi M., Shafiee A. and Foroumadi A. (2010), “Synthesis and cytotoxic activity of some 2-amino-4-aryl-3-cyano-7-(dimethylamino)-4H-chromenes”, Research in Pharmaceutical Sciences, 5(1), 9-14.
[4] Kemnitzer W., Drewe J., Jiang S., Zhang H., Zhao J., Crogan-Grundy C., Xu L., Lamothe S., Gourdeau H., Denis R., Tseng B., Kasibhatla S., Cai S.X. (2007), “Discovery of 4-Aryl-4H-chromenes as a New Series of Apoptosis Inducers Using a Cell- and Caspase-Based High-Throughput Screening Assay. 3. Structure-Activity Relationships of Fused Rings at the 7,8-Positions”, Journal of Medicinal Chemistry, 50, 2858-2864.
[5] Keerthy H.K., Garg M., Mohan C.D., Madan V., Kanojia D., Shobith R., Nanjundaswamy S., Mason D.J., Bender A., Basappa, Rangappa K.S., Koeffler H.P. (2014), “Synthesis and Characterization of Novel 2-Amino-Chromene-Nitriles that Target Bcl-2 in Acute Myeloid Leukemia Cell Lines”, PLoS One, 9, 107–118.
[6] Javanshir Sh., Safari M. and Dekamin M.G. (2014), “A facile and green three-component synthesis of 2-amino-3-cyano-7-hydroxy-4H-chromenes on grinding”, Scientia Iranica C 21(3), 742-747.
[7] Behbahani F.K. and Mehraban S. (2015), “Synthesis of 2-Amino-3-cyano-7-hydroxy-4H-chromenes Using L-Proline as a Biocatalyst”, Journal of the Korean Chemical Society, 59(4), 284-288.
[8] Safari J., Zarnegar Z., Heydarian M. (2012), “Magnetic Fe3O4 Nanoparticles as Efficient and Reusable Catalyst for the Green Synthesis of 2-Amino-4H-chromene in Aqueous Media”, Bulletin of the Chemical Society of Japan, 85(12), 1332-1338.