Silica sulfuric acid as a recyclable catalyst for a one-pot synthesis of α-aminophosphonates in solvent-free conditions

Letters in Organic Chemistry

Volumn 6, Issue 6, 2009, Pages 470-473

  Yang, Jing Jun ^a   Dang, Jin Ning ^a   Chang, Yu Wei ^a  

^a GANSU NORMAL UNIVERSITY FOR NATIONALITIES   (China)

Author keywords

Aminophosphonates; Aldehydes; Alkyl phosphite; Amines; Three component reaction

Indexed keywords

EID: 70349106721     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017809789124830     Document Type: Article

References (49)

1. (a) Schug, K. A.; Lindner. W. Chem. Rev., 2005, 105, 67;
2. (b) Moonen, K.; Laureyn, I.; Stevens, C. V. Chem. Rev. 2004, 104, 6177.
3. Kafarski, P.; Leczak, B. Phosphorus, Sulfur Silicon Relat. Elem., 1991, 63, 193.
4. (a) Hirschmann, R.; Smith, A. B.; III; Taylor, C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengeler, P. A.; Benkovic, S. J. Science, 1994, 265, 234;
5. (b) Smith, A. B., III; Taylor, C. M.; Benkovic, S. J.; Hirschmann, R. Tetrahedron Lett., 1994, 35, 6853.
6. (a) Atherton, F. R.; Hassall, C. H.; Lambert, R. W. J. Med. Chem., 1986, 29, 29;
7. (b) Allen, J. G.; Atherton, F. R.; Hall, M. J.; Hassal, C. H.; Holmes, S. W.; Lambert, R. W.; Nisbet, L. J.; Ringrose, P. S. Nature, 1978, 272, 56;
8. (c) Allen, J. G.; Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Holmes, S. W.; Lambert, R. W.; Nisbet, L. J.; Ringrose, P. S. Antimicrob. Agents Chemother. 1979, 15, 684;
9. (d) Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Lambert, R. W.; Ringrose, P. S. Antimicrob. Agents Chemother., 1979, 15, 677;
10. (e) Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Lambert, R. W.; Lloyd, W. J.; Ringrose, P. S. Antimicrob. Agents Chemother., 1979, 15, 696.
11. Hassall, C. H. In Antibiotics;Hahn, E. F. Ed.; Springer-Verlag: Berlin, 1983; Vol. VI, pp. 1-11.
12. (a) Petrov, K. A.; Chauzov, V. A.; Erokhina, T. S. Usp. Khim., 1974, 43, 2045
13. Chem. Abstr. 1975, 82, 43486;
14. (b) Kirby, A. J.; Warren, S. G. The Organic Chemistry of Phosphorus; Elsevier: Amsterdam, 1967;
15. (c) Laschat, S.; Kunz, H. Synthesis, 1992, 90;
16. (d) Zon, J. Pol. J. Chem., 1981, 55, 643;
17. (e) Hosseini-Sarvari, M. Tetrahedron, 2008, 64, 5459.
18. Genêt, J. P.; Uziel, J.; Port, M.; Touzin, A. M.; Roland, S.; Thorimbert, S.; Tanier, S. Tetrahedron Lett., 1992, 33, 77.
19. (a) Heydari, A.; Javidan, A.; Shaffie, M. Tetrahedron Lett., 2001, 42, 8071;
20. (b) Saidi, M. R.; Azizi, N. Synlett, 2002, 1347;
21. (c) Ranu, B. C.; Hajra, A.; Jana, U. Org. Lett., 1999, 1, 1141;
22. (d) Qian, C.; Huang, T. J. Org. Chem., 1998, 63, 4125;
23. (e) Manabe, K.; Kobayashi, S. Chem. Commun. (Cambridge, UK), 2000, 669;
24. (f) Lee, S.-G.; Park, J. H.; Lee, J. K.; Kang, J. Chem. Commun. (Cambridge, UK), 2001, 1698;
25. (g) Chandrasekhar, S.; Prakash, S. J.; Jagadeshwar, V.; Narsihmulu, Ch. Tetrahedron Lett., 2001, 42, 5561;
26. (h) Yadav, J. S.; Reddy, B. V. S.; Madan, C. Synlett, 2001, 1131;
27. (i) Kaboudin B.; Nazari, R. Tetrahedron Lett., 2001, 42, 8211;
28. (j) Zhan, Z.-P.; Li, J.-P. Synth. Commun., 2005, 35, 2501;
29. (k) Zhan, Z.-P.; Yang, R.-F.; Li, J.-P. Chem. Lett., 2005, 34, 1042;
30. (l) Reddy, K. R.; Reddy, K. S.; Reddy, C. V.; Mahesh, M.; Raju, P. V. K.; Reddy, V. V. N. Chem. Lett., 2005, 34, 444;
31. (m) Sun, P.; Hu, Z.; Huang, Z. Synth. Commun., 2004, 34, 4293;
32. (n) Ghosh, R.; Maiti, S.; Chakraborty, A.; Maiti, D. K. J. Mol. Catal. A: Chem., 2004, 210, 53;
33. (o) Xu, F.; Luo, Y.; Deng, M.; Shen, Q. Eur. J. Org. Chem., 2003, 4728;
34. (p) Azizi, N.; Rajabi, F.; Saidi, M. R. Tetrahedron Lett., 2004, 45, 9233;
35. (q) Wu, J.; Sun, W.; Xia, H.-G.; Sun, X. Org. Biomol. Chem., 2006, 4, 1663;
36. (r) Bhagat, S.; Chakraborti, A. K. J. Org. Chem. 2007, 72, 1263;
37. (s) Bhagat, S.; Chakraborti, A. K. J. Org. Chem. 2008, 73, 6029.
38. (a) Chene, W.-Y.; Lu, J. Synlett, 2005, 2293; 1
39. (b) Zolfigol, M. A. Tetrahedron, 2001, 57, 9509;
40. (c) Zolfigol, M. A.; Bamoniri, A. Synlett, 2002, 1621;
41. (d) Zolfigol, M. A.; Madrakian, E.; Ghaemi, E. Molecules, 2002, 7, 734;
42. (e) Mirjalili, B. F.; Zolfigol, M. A.; Bamoniri, A. Molecules, 2002, 7, 751;
43. (f) Zolfigol, M. A.; Shirini, F.; Choghamarani, A. G.; Mohammadpoor-Baltork, I. Green Chem., 2002, 4, 562;
44. (g) Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Fard, M. A. B. Tetrahedron Lett., 2003, 44, 2889.
45. (a) Varma, R. S. Green Chem., 1999, 1, 43;
46. (b) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron, 2001, 57, 9225.
47. 2 (2×10 mL). The product (silica sulfuric acid, 36.00 g) was obtained.
48. 6P : C, 58.67; H, 6.89; N, 3.42. Found: C, 58.76; H, 7.01.
49. 6P: C, 54.68; H, 7.56; N, 3.75. Found: C, 54.73; H, 7.48; N, 3.80.