1, 3-Disulfonic acid imidazolium hydrogen sulphate as an efficient and reusable ionic liquid for the multicomponent synthesis of polyhydroquinoline derivatives under solvent-free conditions
作者： Kamal Mohammadi , Farhad Shirini , Asieh Yahyazadeh
DOI: 10.1007/S11164-015-2134-Y
关键词: Catalysis 、 Organic chemistry 、 Ionic liquid 、 Chemistry 、 Ammonium acetate 、 Hydrogen 、 Condensation 、 Solvent free 、 Reusability 、 Ethyl acetoacetate
摘要: A facile and highly effective one-pot synthesis of polyhydroquinoline derivatives is reported via Hantzsch condensation aldehydes, 1,3-dicarbonyl compounds, ethyl acetoacetate, ammonium acetate in the presence 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient recyclable ionic liquid under solvent-free conditions. This methodology offers several advantages such short reaction times, high yields, environmentally benign, mild conditions, simple work-up procedure, reusability liquid.
springer.com
sci-hub.se 参考文章(47)
Paul T. Anastas, John Charles Warner, Green Chemistry: Theory and Practice ,(1998)
Gabriela Guillena, Diego J. Ramón, Miguel Yus, Organocatalytic enantioselective multicomponent reactions (OEMCRs) Tetrahedron-asymmetry. ,vol. 18, pp. 693- 700 ,(2007) , 10.1016/J.TETASY.2007.03.002
Claire C. A. Cariou, Guy J. Clarkson, Michael Shipman, Rapid synthesis of 1,3,4,4-tetrasubstituted beta-lactams from methyleneaziridines using a four-component reaction. Journal of Organic Chemistry. ,vol. 73, pp. 9762- 9764 ,(2008) , 10.1021/JO801664G
Farhad Shirini, Nader Ghaffari Khaligh, Somayeh Akbari-Dadamahaleh, Preparation, characterization and use of 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient, halogen-free and reusable ionic liquid catalyst for the trimethylsilyl protection of hydroxyl groups and deprotection of the obtained trimethylsilanes Journal of Molecular Catalysis A-chemical. ,vol. 365, pp. 15- 23 ,(2012) , 10.1016/J.MOLCATA.2012.08.002
Zhiwei Chen, Qiang Zhu, Weike Su, A novel sulfonic acid functionalized ionic liquid catalyzed multicomponent synthesis of 10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-dione derivatives in water Tetrahedron Letters. ,vol. 52, pp. 2601- 2604 ,(2011) , 10.1016/J.TETLET.2011.03.059
Satish Kumar, Poonam Sharma, Kamal K. Kapoor, Maninder Singh Hundal, An efficient, catalyst- and solvent-free, four-component, and one-pot synthesis of polyhydroquinolines on grinding Tetrahedron. ,vol. 64, pp. 536- 542 ,(2008) , 10.1016/J.TET.2007.11.008
Mei Hong, Chun Cai, Wen-Bin Yi, Hafnium (IV) bis(perfluorooctanesulfonyl)imide complex catalyzed synthesis of polyhydroquinoline derivatives via unsymmetrical Hantzsch reaction in fluorous medium Journal of Fluorine Chemistry. ,vol. 131, pp. 111- 114 ,(2010) , 10.1016/J.JFLUCHEM.2009.10.009
Piyush N. Kalaria, Shailesh P. Satasia, Dipak K. Raval, Synthesis, characterization and pharmacological screening of some novel 5-imidazopyrazole incorporated polyhydroquinoline derivatives. European Journal of Medicinal Chemistry. ,vol. 78, pp. 207- 216 ,(2014) , 10.1016/J.EJMECH.2014.02.015
Alessandro Dondoni, Alessandro Massi, Erik Minghini, Valerio Bertolasi, Multicomponent Hantzsch cyclocondensation as a route to highly functionalized 2- and 4-dihydropyridylalanines, 2- and 4-pyridylalanines, and their N-oxides: preparation via a polymer-assisted solution-phase approach Tetrahedron. ,vol. 60, pp. 2311- 2326 ,(2004) , 10.1016/J.TET.2004.01.011
Niraj K. Ladani, Divyesh C. Mungra, Manish P. Patel, Ranjan G. Patel, Microwave assisted synthesis of novel Hantzsch 1,4-dihydropyridines, acridine-1,8-diones and polyhydroquinolines bearing the tetrazolo[1,5-a]quinoline moiety and their antimicrobial activity assess Chinese Chemical Letters. ,vol. 22, pp. 1407- 1410 ,(2011) , 10.1016/J.CCLET.2011.07.009