Nanomagnetically modified sulfuric acid (γ-Fe2O3@SiO2-OSO3H): An efficient, fast, and reusable green catalyst for the Ugi-like Groebke-Blackburn-Bienaymé three-component reaction under solvent-free conditions

Tetrahedron Letters

Volumn 53, Issue 39, 2012, Pages 5257-5260

  Rostamnia, Sadegh ^a   Lamei, Kamran ^a   Mohammadquli, Mohsen ^b   Sheykhan, Mehdi ^b   Heydari, Akbar ^b  

^a UNIVERSITY OF MARAGHEH   (Iran)

^b TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

Encapsulated iron oxide nanoparticles; Green chemistry; Magnetically recoverable nanocatalyst; Modified sulfuric acid; Ugi like multicomponent reaction

Indexed keywords

EID: 84878011982     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.07.075     Document Type: Article

References (33)

1. P.T. Anastas, and J.C. Warner Green Chemistry: Theory and Practice 1998 Oxford University Press Oxford pp. 1-30
2. K. Tanaka, and F. Toda Chem. Rev. 1025 2000 100
3. A.H. Latham, and M.E. Williams Acc. Chem. Res. 41 2008 411
4. A. Hu, G.T. Yee, and W. Lin J. Am. Chem. Soc. 127 2005 12486
5. M. Mojtahedi, M.S. Abaee, and T. Alishiri Tetrahedron Lett. 50 2009 2322
6. L. Mamani, A. Heydari, and M. Sheykhan Appl. Catal., A Gen. 384 2010 122
7. L.F. Tietze Chem. Rev. 96 1996 115
8. A. Dömling, and I. Ugi Angew. Chem., Int. Ed. 39 2000 3169
9. Y. Rival, G. Grassy, and G. Michel Chem. Pharm. Bull. 40 1992 1170
10. A. Gueiffier, S. Mavel, M. Lhassani, A. Elhakmaoui, R. Snoeck, G. Andrei, O. Chavignon, J.C. Teulade, M. Witvrouw, J. Balzarini, E. De-Clercq, and J.P. Chapat J. Med. Chem. 41 1998 5108
11. A. Elhakmaoui, A. Gueiffier, J.C. Milhavet, Y. Blache, J.P. Chapat, O. Chavignon, J.C. Teulade, R. Snoeck, G. Andrei, and E. De-Clercq Bioorg. Med. Chem. Lett. 1994 1937 4
12. K. Groebke, L. Weber, and F. Mehlin Synlett 1998 661
13. H. Bienayme, and K. Bouzid Angew. Chem., Int. Ed. 37 1998 2234
14. J.J. Chen, A. Golebiowski, J. Clenaghan, S.R. Klopfenstein, and L. West Tetrahedron Lett. 42 2001 2269
15. A. Shaabani, E. Soleimani, A. Maleki, and J. Moghimi-Rad Synth. Commun. 1090 2008 38
16. A. Shaabani, A. Maleki, J. Rad, and E. Soleimani Chem. Pharm. Bull. 55 2007 957
17. G.B. Blackburn, P. Fleming, K. Shiosaki, and S. Tsai Tetrahedron Lett. 39 1998 3635
18. L.R. Odell, M. Nilsson, J. Gising, O. Lagerlund, D. Muthas, A. Nordqvist, A. Karlen, and M. Larhed Bioorg. Med. Chem. Lett. 19 2009 4790
19. A. Shaabani, E. Soleimani, A. Sarvary, A.H. Rezayan, and A. Maleki Chin. J. Chem. 27 2009 369
20. S.K. Guchhait, and C. Maadan Synlett 2009 628
21. A.L. Rousseau, P. Matlaba, and C.J. Parkinson Tetrahedron Lett. 48 2007 4079
22. M. Sheykhan, L. Mamani, A. Ebrahimi, and A. Heydari J. Mol. Catal. A: Chem. 335 2011 253
23. L. Mamani, M. Sheykhan, and A. Heydari Appl. Catal., A: Gen. 395 2011 34
24. L. Mamani, M. Sheykhan, A. Heydari, M. Faraji, and Y. Yamini Appl. Catal., A: Gen. 377 2010 64
25. S. Rostamnia, and K. Lamei Synthesis 2011 3080
26. A. Alizadeh, S. Rostamnia, and A.A. Esmaili Synthesis 2007 709
27. A. Alizadeh, Q. Oskueyan, and S. Rostamnia Synthesis 2007 2637
28. A. Alizadeh, N. Zohreh, and S. Rostamnia Tetrahedron 63 2007 8083
29. A. Alizadeh, and S. Rostamnia Synthesis 2008 57
30. 2 was evaporated under reduced pressure and the residue was subjected to column chromatography on silica gel using EtOAc-n-hexane (2:1) as the eluent to afford the aminoimidazopyridine product 4 in high purity. All the isolated products gave satisfactory spectral and physical data. The isolated catalyst could be recycled, see Supplementary data for details.
31. I. Ugi Angew. Chem., Int. Ed. Engl. 21 1982 810
32. A. Dömling Curr. Opin. Chem. Biol. 6 2002 306
33. I. Ugi, A. Dömling, and B. Werner J. Heterocycl. Chem. 37 2000 647