One-pot access to pyridocoumarins via Povarov-hydrogen transfer cascade under auto-tandem catalysis of iodine in aqueous micelles

Tetrahedron Letters

Volumn 55, Issue 9, 2014, Pages 1564-1568

  Ganguly, Nemai C ^a   Chandra, Sumanta ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

Aqueous micelles; Auto tandem catalysis; Iodine; Povarov hydrogen transfer; Pyridocoumarins

Indexed keywords

EID: 84894097701     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.01.078     Document Type: Article

References (45)

1. P.J. Rosenthal Antimalarial Chemotherapy: Mechanisms of Action, Resistance and New Directions in Drug Discovery 2001 Humana: Totowa NJ
2. A. von Sprecher, M. Gerspacher, A. Beck, S. Kimmel, H. Wiestner, G.P. Anderson, U. Niederhauser, N. Subramanian, and M.A. Bray Bioorg. Med. Chem. Lett. 8 1998 965
3. P.L. Ferrarini, C. Mori, M. Badawneh, V. Calderone, R. Greco, C. Manera, A. Martinelli, P. Nieri, and G. Saccomanni Eur. J. Med. Chem. 35 2000 815
4. G. Roma, M.D. Braccio, G. Grossi, F. Mattioli, and M. Ghia Eur. J. Med. Chem. 35 2000 1021
5. A. Kleeman, and J. Engel Pharmaceutical Substances 4th ed. 2001 Thieme: New York NY 482
6. A. Kleeman, and J. Engel Pharmaceutical Substances 4th ed. 2001 Thieme: NewYork NY 1479
7. S. Concilio, P.M. Pfister, N. Tirelli, C. Kocher, and U.W. Suter Macromolecules 34 2001 3607
8. H.S. Nalwa, M. Suzuki, A. Takahashi, and A. Kageyama Appl. Phys. Lett. 72 1998 1311
9. J.V. Johnson, S. Rauckman, P.D. Baccanari, and B. Roth J. Med. Chem. 1989 1942 32
10. N. Yamada, S. Kadowaki, K. Takahashi, and K. Umezu Biochem. Pharmacol. 44 1992 1211
11. M.J. Laughlin, and R.P. Hsung J. Org. Chem. 66 2001 1049
12. J.P. Michael Nat. Prod. Rep. 22 2005 627
13. M. Gao, D. Kong, A. Clearfield, and Q.-H. Zheng Bioorg. Med. Chem. Lett. 16 2006 2229
14. P. Cheng, N. Huang, J.-Y. Jiang, Q. Zhang, Y.-T. Zheng, J.-J. Chen, X.-M. Zhang, and Y.-B. Ma Bioorg. Med. Chem. Lett. 18 2008 2475
15. R.V.A. Orru, and E. Ruijter B.U.W. Maes, Synthesis of Heterocycles via Multicomponent Reactions Vols. 1-2 2010 Springer Berlin
16. For a review of Povarov reactions, see: V.V. Kouznetsov Tetrahedron 65 2009 2721
17. A. Kumar, S. Srivastava, G. Gupta, V. Chaturvedi, S. Sinha, and R. Srivastava ACS Comb. Sci. 13 2011 65 and reference cited therein
18. C.J. O' Connor, H.S.G. Beckmann, and D.R. Spring Chem. Soc. Rev. 41 2012 4444
19. K.M.G. O' Connel, M. Diaz-Gaivlán, W.R.J.D. Galloway, and D.R. Spring Bielstein J. Org. Chem. 8 2012 850
20. W.R.J.D. Galloway, A. Isidro-Llobet, and D.R. Spring Nat. Commun. 1 2010 80
21. T.E. Nielsen, and S.L. Schreiber Angew. Chem., Int. Ed. 47 2008 48
22. A.T. Khan, D.K. Das, K. Islam, and P. Das Tetrahedron Lett. 53 2012 6418
23. A.A. Kudale, D.O. Miller, L.N. Dawe, and G.J. Bodwell Org. Biomol. Chem. 9 2011 7196
24. A.A. Kudale, J. Kendall, D.O. Miller, J.L. Collins, and G.J. Bodwell J. Org. Chem. 73 2008 8437
25. N.C. Ganguly, S. Chandra, and S.K. Barik Synth. Commun. 43 2013 1351
26. N.C. Ganguly, P. Mondal, and S. Roy Tetrahedron Lett. 54 2013 2386
27. N.C. Ganguly, S. Roy, P. Mondal, and R. Saha Tetrahedron Lett. 53 2012 7067
28. N.C. Ganguly, P. Mondal, and S.K. Barik Green Chem. Lett. Rev. 5 2012 73
29. For a very recent review on iodine-catalyzed organic reactions, see: Y.-M. Ren, C. Cai, and R.-C. Yang RSC Adv. 3 2013 7182
30. J.S. Yadav, B.V.S. Reddy, T.S. Rao, K. Bhavani, and A. Raju Tetrahedron Lett. 51 2010 2622
31. P. Theerthagiri, A. Lalitha, and P.N. Arunachalam Tetrahedron Lett. 51 2010 2813
32. S.J. Lee, J.J. Lee, C.-H. Kim, Y.M. Jun, M.M. Lee, and B.H. Kim Tetrahedron Lett. 50 2009 484
33. J.S. Yadav, B.V.S. Reddy, N. Thrimurtulu, N.M. Reddy, and A.R. Prasad Tetrahedron Lett. 49 2008 2031
34. Z. Huo, H. Tomeba, and Y. Yamamoto Tetrahedron Lett. 49 2008 5531
35. S. Das, R. Borah, R.R. Devi, and A.J. Thakur Synlett 2008 2741
36. M. Jereb, D. Vražič, and M. Zupan Tetrahedron 67 2011 1355
37. For a review of 'on water' reactions, see: A. Chanda, and V.V. Fokin Chem. Rev. 109 2009 725
38. G. Bhargava, C. Mohan, and M.P. Mahajan Tetrahedron 64 2008 3017
39. N. Shinodh, H. Tokuyama, Y. Takemoto, and K. Takasu J. Org. Chem. 73 2008 7451
40. N. Shinodh, H. Tokuyama, and K. Takasu Tetrahedron Lett. 48 2007 4749
41. S. Cerritelli, M. Chiarini, G. Cerichelli, M. Capone, and M. Marsili Eur. J. Org. Chem. 2004 623
42. R.A. Batey, P.D. Simoncic, D. Lin, R.P. Smyj, and A.J. Lough Chem. Commun. 1999 651
43. C.-J. Li, and T.H. Chan Organic Reactions in Aqueous Media 1997 Wiley New York
44. S. Kobayashi, M. Araki, and M. Yasuda Tetrahedron Lett. 36 1995 5773
45. X.-H. Wang, M.-Y. Yin, W. Wang, and S.-J. Tu Eur. J. Org. Chem. 2012 4811