Michael addition of α-azido ketones on iminocoumarin derivatives: An efficient access to new functionalized azido chromenes

Tetrahedron Letters

Volumn 52, Issue 32, 2011, Pages 4093-4096

  Babu, Thelagathoti Hari ^a   Kamalraja, Jayabal ^a   Muralidharan, Doraiswamy ^a   Perumal, Paramasivan T ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

Azido ketones; Azido chromenes; Michael addition; Triazolyl chromenes

Indexed keywords

AZIDE; CHROMENE DERIVATIVE; COUMARIN DERIVATIVE; KETONE DERIVATIVE; MALONONITRILE; SALICYLALDEHYDE;

ARTICLE; BIOTRANSFORMATION; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CYCLOADDITION; MICHAEL ADDITION; ONE POT SYNTHESIS;

EID: 79960417422     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.05.101     Document Type: Article

References (32)

1. P. Langer, I. Freifeld, and H. Shojaei Chem. Commun. 2003 3044
2. I. Freifeld, H. Shojaei, and P. Langer J. Org. Chem. 71 2006 4965
3. I. Freifeld, H. Shojaei, R. Dede, and P. Langer J. Org. Chem. 71 2006 6165
4. E.C.S. Brenelli, and J.L.N. Fernandes Tetrahedron: Asymmetry 14 2003 1255
5. S.R. Wallner, I. Lavandera, S.F. Mayer, R. Öhrlein, A. Hafner, K. Edegger, K. Faber, and W. Kroutil J. Mol. Catal. B: Enzym. 55 2008 126
6. T. Benaissa, S. Hamman, and C.G. Beguin J. Fluorine Chem. 38 1988 163
7. M. Nakajima, C.A. Loeschorn, W.E. Cimbrelo, and J.P. Anselme Org. Prep. Proced. Int. 12 1980 265
8. Y.G. Gololobov, I.N. Zhmurova, and L.F. Kasukhin Tetrahedron 37 1981 437
9. Y.G. Gololobov, and L.F. Kasukhin Tetrahedron 48 1992 1353
10. S. Eguchi, Y. Matsushita, and K. Yamashita Org. Prep. Proced. Int. 24 1992 209
11. P. Molina, and M.J. Vilaplana Synthesis 1994 1197
12. H. Wamhoff, G. Richardt, and S. Stolben A.R. Katritzky, Advances in Heterocyclic Chemistry Vol. 64 1995 Academic Press San Diego 159 240
13. J. Barluenga, and F. Palacios Org. Prep. Proced. Int. 23 1991 1
14. F. Palacios, C. Alonso, D. Aparicio, G. Rubiales, and J.M. de los Santos Tetrahedron 63 2007 523
15. J.L. Marco, A. Martinez-Grau, N. Martin, and C. Seoane Tetrahedron Lett. 36 1995 5393
16. G. Savitha, S.K. Niveditha, D. Muralidharan, and P.T. Perumal Tetrahedron Lett. 48 2007 2943
17. G. Shanthi, and P.T. Perumal Tetrahedron Lett. 48 2007 6785
18. G. Shanthi, G. Subbulakshmi, and P.T. Perumal Tetrahedron 63 2007 2057
19. T.H. Babu, G. Shanthi, and P.T. Perumal Tetrahedron Lett. 50 2009 2881
20. N.P. Selvam, T.H. Babu, and P.T. Perumal Tetrahedron 65 2009 8524
21. G.P. Ellis A. Weissberger, E.C. Taylor, The Chemistry of Heterocyclic Compounds. Chromenes, Chromanes and Chromones 1977 John Wiley New York 11 141 Chapter II
22. E.A. Hafez, M.H. Elnagdi, A.G.A. Elagamey, and F.M.A.A. El-Taweel Heterocycles 26 1987 903
23. G. Shanthi, and P.T. Perumal Synlett 2008 2791
24. P. Jayashree, G. Shanthi, and P.T. Perumal Synlett 2009 917
25. See, for example: G.A. Cordell The Alkaloids: Chemistry and Biology Vol. 54 2000 Academic Press San Diego, CA and others in this series
26. É. Juhász-Tóth, and T. Patonay Eur. J. Org. Chem. 2002 3055
27. T. Patonay, É. Juhász-Tóth, and A. Bényei Eur. J. Org. Chem. 2002 285
28. For a review on copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis, see: G. Evano, N. Blanchard, and M. Toumi Chem. Rev. 108 2008 3054
29. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004
30. R. Huisgen A. Padwa, 1,3-Dipolar Cycloaddition Chemistry Vol. 1 1984 Wiley New York 1 177
31. C.W. Tornøe, C. Christensen, and M. Meldal J. Org. Chem. 67 2002 3057
32. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596