Efficient one-pot synthesis of β-phosphono malonates and 2-amino-4H-chromen-4-ylphosphonate derivatives by ethylenediamine diacetate-catalyzed three-component reactions

Tetrahedron

Volumn 68, Issue 1, 2012, Pages 226-237

  Kolla, Srinivasa Rao ^a   Lee, Yong Rok ^a  

^a Yeungnam University   (South Korea)

Author keywords

Phosphono malonates; 2 Amino 4H chromen 4 ylphosphonate; Ethylenediamine diacetate; Three component reactions

Indexed keywords

ACETOACETIC ACID; CHROMENE DERIVATIVE; ETHYLENEDIAMINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; SALICYLALDEHYDE;

ARTICLE; CHEMICAL REACTION; ONE POT SYNTHESIS; PRIORITY JOURNAL;

EID: 82255175431     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.10.060     Document Type: Article

References (42)

1. J.D. Smith R.L. Hilderbrand, The Role of Phosphonates in Living Systems 1983 CRC Boca Raton, FL 31 53
2. M.C. Allen, W. Fuhrer, B. Tuck, R. Wade, and J.M. Wood J. Med. Chem. 32 1989 1652
3. D.V. Patel, K. Rielly-Gauvin, and D.E. Ryono Tetrahedron Lett. 31 1990 5587
4. B. Stowasser, K.H. Budt, J.Q. Li, A. Peyman, and D. Ruppert Tetrahedron Lett. 33 1992 6625
5. P. Kafarski, and B. Lejczak Phosphorus, Sulfur Silicon Relat. Elem. 63 1991 193
6. E.K. Baylis, C.D. Campbell, and J.G. Dingwall J. Chem. Soc., Perkin Trans. 1 1984 2845
7. F.R. Atherton, C.H. Hassall, and R.W. Lambert J. Med. Chem. 29 1986 29
8. B.E. Maryanoff, and A.B. Reitz Chem. Rev. 89 1989 863
9. M. Hayashi, Y. Matsuura, Y. Nishimura, T. Yamasaki, Y. Imai, and Y. Watanabe J. Org. Chem. 72 2007 7798
10. M. Kalek, and J. Stawinski Organometallics 26 2007 5840
11. A.N. Pudovik, and I.V. Konovalova Synthesis 1979 81
12. D. Simoni, F.P. Invidiata, M. Manferdini, I. Lampronti, R. Rondanin, M. Roberti, and G.P. Pollini Tetrahedron Lett. 39 1998 7615
13. M. Hosseini-Sarvari, and S. Etemad Tetrahedron 64 2008 5519
14. K. Green Tetrahedron Lett. 30 1989 4807
15. R.R. Hindersinn, and R.S. Ludington J. Org. Chem. 30 1965 4020
16. R.A. Stockland Jr., R.I. Taylor, L.E. Thompson, and P.B. Patel Org. Lett. 7 2005 851
17. M.O. Shulyupin, M.A. Kazankova, and I.P. Beletskaya Org. Lett. 4 2002 761
18. Q. Xu, and L.-B. Han Org. Lett. 8 2006 2099
19. D. Semenzin, G. Etemad-Moghadam, D. Albouy, O. Diallo, and M. Koenig J. Org. Chem. 62 1997 2414
20. L.-B. Han, and C.-Q. Zhao J. Org. Chem. 70 2005 10121
21. S. Sobhani, Z.P. Parizi, and S. Rezazadeh J. Organomet. Chem. 696 2011 813
22. S. Sobhani, and S. Rezazadeh Synlett 2010 1485
23. Z. Jiang, Y. Zhang, W. Ye, and C.-H. Tan Tetrahedron Lett. 48 2007 51
24. S. Sobhani, and Z.P. Parizi Tetrahedron 67 2011 3540
25. G.P. Ellis Chromenes, harmones, and chromones A. Weissberger, E.C. Taylor, The Chemistry of Heterocyclic Compounds 1977 John Wiley New York, NY 11 139 Chapter II
26. E.A.A. Hafez, M.H. Elnagdi, A.G.A. Elagamey, and F.M.A.A. El-Taweel Heterocycles 26 1987 903
27. Li, C. J.; Li, Y. L. U.S. Patent Appl. Publ. U.S. 2,005,222,246 Al 20,051,006, 2005.
28. M. Ough, A. Lewis, E.A. Bey, J. Gao, J.M. Ritchie, W. Bornmann, D.A. Boothman, L.W. Oberley, and J.J. Cullen Cancer Biol. Ther. 4 2005 95
29. D.O. Moon, Y.H. Choi, N.D. Kim, Y.M. Park, and G.Y. Kim Int. Immunopharmacol. 7 2007 506
30. V.F. De Andrade-Neto, M.O.F. Goulart, J.F. Da Silva Filho, M.J. Da Silva, M.D.C.F.R. Pinto, A.V. Pinto, M.G. Zalis, L.H. Carvalho, and A.U. Krettli Bioorg. Med. Chem. Lett. 14 2004 1145
31. P.S. Elisa, E.B. Ana, A.G. Ravelo, D.J. Yapu, and A.G. Turba Chem. Biodivers. 2 2005 264
32. A.M. Shestopalov, Y.M. Emelianova, and V.N. Nesterov Russ. Chem. Bull. 52 2003 1164
33. P. Jayashree, G. Shanthi, and P.T. Perumal Synlett 2009 917
34. S.N. Murthy, B. Madhav, V.P. Reddy, and Y.V.D. Nageswar Tetrahedron Lett. 51 2010 3649
35. C. Bolm, T. Rantanen, I. Schiffers, and L. Zani Angew. Chem., Int. Ed. 44 2005 1758
36. D.J. Berrisford, C. Bolm, and K.B. Sharpless Angew. Chem., Int. Ed. Engl. 34 1995 1059
37. S. Saito, M. Nakadai, and H. Yamamoto Synlett 2001 1245
38. S. Saito, and H. Yamamoto Acc. Chem. Res. 37 2004 570
39. S.E. Denmark, B.M. Eklov, P.J. Yao, and M.D. Eastgate J. Am. Chem. Soc. 131 2009 11770
40. S.E. Denmark, and W.-J. Chung J. Org. Chem. 71 2006 4002
41. S. Galla, and Y.R. Lee Synthesis 2010 453
42. S.R. Kolla, and Y.R. Lee Tetrahedron 66 2010 8938