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http://dx.doi.org/10.5012/bkcs.2009.30.5.1054

1-Benzyl-3-Methyl Imidazolium Hydrogen Sulphate [bnmim][HSO4] Promoted Synthesis of α-Aminophosphonates  

Sadaphal, Sandip A. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Sonar, Swapnil S. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Kategaonkar, Amol H. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Shingare, Murlidhar S. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Publication Information
Abstract
We have demonstrated a one-pot three component coupling of an aldehydes, an amines, and triethyl phosphite using 1-benzyl-3-methyl imidazolium hydrogen sulphate [bnmim][][$HSO_{4}$] as an efficient catalyst. All the reactions proceed under solvent-free conditions at room temperature. This methodology afforded the corresponding $\alpha$-aminophosphonates in shorter reaction times with excellent yields.
Keywords
1-Benzyl-3-methyl imidazolium hydrogen sulphate [bnmim][$HSO_{4}$]; $\alpha$-Aminophosphonates; Aldehydes/ketone; Amines; Triethyl phosphite;
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1 Thomas, W. Chem. Rev. 1999, 99, 2071   DOI   ScienceOn
2 Sheldon, R. Chem. Commun. 2001, 2399
3 Zhao, D.; Wu, M.; Kou, Y.; Min, K. Catal. Today 2002, 1, 2654
4 Peng, J.; Deng, Y. Tetrahedron Lett. 2001, 42, 4 03   DOI   ScienceOn
5 Shen, Z. L.; Zhou, W. J.; Liu, Y. T.; Ji, S. J.; Loh,T. P. Green Chem. 2008,10, 283   DOI   ScienceOn
6 Fraga-Dubreuil, J.; Bourahla, J. K.; Rahmouni, M.; Bazureau J. P.; Hamelin, J. Catal. Commun. 2002, 3, 185   DOI   ScienceOn
7 Quin L. D.; Quin, G. S. A Guide to Organophosphorus Chemistry; John Wiley & Sons Ltd.: New York, 2000; 351;
8 Corbridge, D. E. C. Phosphorus Chemistry, Biochemistry & Technology; Elsevier: Amsterdam, 2000; p 835
9 Baylis, E. K.; Campbell, C. D.; Dingwall, J. G. J. Chem. Soc., Perkin Trans 1 1984, 2845;   DOI
10 Allen, M. C.; Fuhrer, W.; Truck, B.; Wade, R.; Wood, J. M. J. Med. Chem. 1989, 32, 1652;   DOI
11 Kafraski, P.; Lejezak, B. Phosphorus, Sulfur, Silicon Relat. Elem. 1991, 63, 193;   DOI   ScienceOn
12 Hirschmann, R.; Smith, A. B.; Taylor, C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengler P. A.; Venkovic, S. J. Science 1994, 265, 234   DOI
13 Bhagat, S.; Chakraborti, A. K. J. Org. Chem. 2008, 73, 6029   DOI   ScienceOn
14 Firouzabadi, H.; Iranpoor, N.; Sobhani, S. Synthesis 2004, 2692
15 Elmakssoudi, A.; Zahouily, M.; Mezdar, A.; Rayadh, A.; Sebti, S. Comptes Rendus Chim. 2005, 8, 1954   DOI   ScienceOn
16 Bhagat, S.; Chakraborti, A. K. J. Org. Chem. 2007, 72, 1263   DOI   ScienceOn
17 Kaboudin, B.; Jafari, E. Synlett 2008, 1837
18 Yadav, J. S.; Reddy B. V. S.; Sreedhar, P. Green Chem. 2002, 4, 436   DOI   ScienceOn
19 Gong, K.; He, Z.-W.; Xu, Y.; Fang, D.; Liu, Z.-L. Monatsh. Chem. 2008, 139, 913   DOI   ScienceOn
20 Fischer, T.; Sethi, A.; Welton, T.; Woolf, J. Tetrahedron Lett. 1999, 40, 793   DOI   ScienceOn
21 Le Boulaire, V. R. Chem. Commun. 2000, 2195
22 Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249
23 Ji, S. J.; Jiang, Z. Q.; Lu, J.; Loh, T. P. Synlett 2004, 5, 831
24 Pawar, S. S.; Dekhane, D. V.; Shingare M. S.; Thore, S. N. Tetrahedron Lett. 2008, 49, 4252   DOI   ScienceOn
25 Potdar, M. K.; Mohile S. S.; Salunkhe, M. M. Tetrahedron Lett., 2001, 42, 9285   DOI   ScienceOn
26 Fraga-Dubreuil, J.; Bourahla, J. K.; Rahmouni, M.; Bazureau J. P.; Hamelin, J. Catal. Commun. 2002, 3, 185   DOI   ScienceOn
27 Madje, B. R.; Patil, P. T.; Shindalkar, S. S.; Benjamin S. B.; Shingare M. S.; Dongare, M. K. Catalysis Commun. 2004, 5, 353   DOI   ScienceOn
28 Pawar, S. S.; Uppalla, L. S.; Shingare M. S.; Thore, S. N. Tetrahedron Lett. 2008, 49, 5858   DOI   ScienceOn
29 Pawar, S. S.; Dekhane, D. V.; Shingare M. S.; Thore, S. N. Chin. Chemical Lett. 2008, 19, 1055   DOI   ScienceOn
30 Ghosh, R.; Maiti, S.; Chakraborty, A.; Maiti, D. J. Molecul. Chem. A 2004, 210, 53   DOI   ScienceOn
31 Sun, P. P.; Hu Z. X.; Huang, Z. H. Synth. Commun. 2004, 34, 4293   DOI   ScienceOn
32 Zhan Z. P.; Li, J. P. Synth. Commun. 2005, 35, 2501   DOI   ScienceOn
33 Paraskar A. S.; Sudalai, A. Arkivoc 2006, 10, 183
34 Ambica, K. S.; Taneja, S. C.; Hundal, M. S. Kapoor, K. K. Tetrahedron Lett. 2008, 49, 2208   DOI   ScienceOn
35 Azizi, N.; Rajabi F.; Saidi, M. R. Tetrahedron Lett. 2004, 45, 9233   DOI   ScienceOn
36 Saidi M. R.; Azizi, N. Synlett 2002, 8, 1347
37 Azizi N.; Saidi, M. R. Tetrahedron 2003, 59, 5329   DOI   ScienceOn
38 Akiyama, T.; Sanada, M.; Fuchibe, K. Synlett 2003, 1463
39 Lee, S.; Lee, J. K.; Song, C. E.; Kim, D. C. Bull. Korean Chem. Soc. 2002, 23, 667   DOI   ScienceOn
40 Lee, S.; Park, J. H.; Kang, J.; Lee, J. K. Chem. Commun. 2001, 1698
41 Tanaka, K. F. Chem. Rev. 2000, 100, 1025   DOI   ScienceOn
42 Chavan, V. P.; Mane A. S.; Shingare, M. S. Indian J. Chem. 2001, 40B, 339
43 Mane, A. S.; Chavan, V. P.; Karale, B. K.; Hangarge, R. V.; Gaikwad M. S.; Shingare, M. S. Synth. Commun. 2002, 32, 2633   DOI   ScienceOn
44 Pokalwar, R. U.; Hangarge, R. V.; Maske, P. V.; Shingare, M. S. Arkivoc 2006, (xi), 196
45 Sadaphal, S. A.; Shelke, K. F.; Sonar S. S.; Shingare, M. S. Central Euro. J. Chem. 2008, 6, 662
46 Pokalwar, R. U.; Hangarge, R. V.; Madje, B. R.; Ware M. N.; Shingare, M. S. Phosphorus, Sulfur, Silicon, Relat. Elem. 2008, 183, 1470
47 Hangarge, R. V.; Sonwane, S. A.; Jarikote D. V.; Shingare, M. S. Green Chem. 2001, 3, 310   DOI   ScienceOn
48 Hangarge, R. V.; Jarikote D. V.; Shingare, M. S. Green Chem. 2002, 4, 266   DOI   ScienceOn