Bismuth nitrate-catalyzed versatile Michael reactions

Journal of Organic Chemistry

Volumn 68, Issue 6, 2003, Pages 2109-2114

  Srivastava, Neeta ^a   Banik, Bimal K ^a  

^a UNIVERSITY OF TEXAS MD ANDERSON CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MICHAEL REACTIONS;

AMINES; CATALYSTS; MOISTURE; OXYGEN;

BISMUTH COMPOUNDS;

AMINE; BISMUTH DERIVATIVE; CARBAMIC ACID DERIVATIVE; IMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; NITRATE; ORGANIC COMPOUND; OXYGEN; THIOL DERIVATIVE;

ACIDITY; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; MICHAEL ADDITION; MOISTURE; REACTION ANALYSIS; TECHNIQUE;

AMINES; BISMUTH; CARBAMATES; CATALYSIS; CHROMATOGRAPHY, THIN LAYER; IMIDAZOLES; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NITRATES; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 0037459683     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026550s     Document Type: Article

References (62)

1. (a) Bull, S. D.; Davies, S. G.; Delgado-Ballester, S.; Fenton, G.; Kelly, P. M.; Smith, A. D. Synlett 2000, 1257.
2. (b) Davies, S. G.; McCarthy, T. D. Synlett 1995, 700.
3. Rosenthal, D.; Braundrup, G.; Davis, K. H.; Wall, M. E. J. Org. Chem. 1965, 30, 3689.
4. (a) Clariana, J.; Galvez, N.; Marchi, C.; Moreno-Manas, M.; Vallribera, A.; Mollins, E. Tetrahedron 1999, 55, 7331.
5. (b) Christoffers, J. Eur. J. Org. Chem. 1998, 1259.
6. (c) Giuseppone, N.; Vander Weghe, P.; Mellah, M.; Collin, J. Tetrahedron 1998, 54, 13129.
7. (a) Cabral, J.; Laszlo, P.; Mahe, L.; Montaufier, M.-T.; Randriamahefa, S. L. Tetrahedron Lett. 1989, 30, 3969.
8. (b) Perez, M.; Pleixats, R. Tetrahedron 1995, 51, 8355.
9. (c) Falborg, L.; Jorgensen, K. A. J. Chem. Soc., Perkin Trans. 1996, 1, 2823.
10. (d) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615.
11. (e) Sibi, M. P.; Liu, M. Org. Lett. 2000, 2, 3393.
12. (f) Zhuang, W.; Hazell, R. G.; Jorgensen, K. A. Chem. Commun. 2001, 1240; For a review for enantioselective conjugate addition, see: Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.
13. (f) Zhuang, W.; Hazell, R. G.; Jorgensen, K. A. Chem. Commun. 2001, 1240; For a review for enantioselective conjugate addition, see: Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.
14. (a) Bandini, M.; Cozzi, P. G.; Giacomoni, M.; Melchiorre, P.; Selva, S.; Ronchi, A. U. J. Org. Chem. 2002, 67, 3700.
15. (b) Yadav, J. S.; Abraham, S.; Reddy, B. V. S.; Sabitha, G. Synthesis 2001, 2165.
16. Yadav, J. S.; Abraham, S.; Reddy, B. V. S.; Sabitha, G. Tetrahedron Lett. 2001, 42, 8063.
17. Kobayashi, S.; Kakumoto, K.; Sugiura, M. Org. Lett. 2002, 4, 1319.
18. (a) Becker, F. F.; Banik, B. K. Bioorg. Med. Chem. Lett. 1998, 8, 2877.
19. (b) Becker, F. F.; Mukhopadhyay, C., Hackfeld, L., Banik, I.; Banik, B. K. Bioorg. Med. Chem. 2000, 8, 2693.
20. (c) Banik, B. K.; Becker, F. F. Bioorg. Med. Chem. 2001, 9, 593.
21. (d) Banik, B. K.; Becker, F. F. Cur. Med. Chem. 2001, 8, 1513.
22. (a) Becker, F. F.; Banik, B. K. U.S. Patent 6,015,811, 2000.
23. (b) Becker, F. F.; Banik, B. K. U.S. Patent 6,184,224, 2001.
24. (c) Becker, F. F.; Banik, B. K. U.S. Patent 0,-103,191, 2002, A1.
25. (d) Becker, F. F.; Banik, B. K. U.S. Patent 6,362,-200, 2002.
26. (a) Ghatak, A.; Becker, F. F.; Banik, B. K. Heterocycles 2000, 53, 2769.
27. (b) Banik, B. K.; Ghatak, A.; Becker, F. F. J. Chem. Soc., Perkin Trans 1 2000, 2179.
28. (c) Banik, B. K.; Becker, F. F. Tetrahedron Lett. 2000, 41, 6551.
29. (d) Ng, S.; Banik, I.; Okawa, A.; Becker, F. F.; Banik, B. K. J. Chem. Res. 2001, 118.
30. (e) Dasgupta, S. K.; Banik, B. K. Tetrahedron Lett. 2002, 43, 9445.
31. (f) Banik, I.; Becker, F. F.; Banik, B. K. J. Med. Chem. 2003, in press.
32. (g) Banik, I.; Hackfeld, L.; Banik, B. K. Heterocycles 2003, in press.
33. (a) Banik, B. K.; Mukhopadhyay, C.; Venkatraman, M. S.; Becker, F. F. Tetrahedron Lett. 1998, 39, 7243.
34. (b) Banik, B. K.; Ghatak, A.; Mukhopadhyay, C.; Becker, F. F. Synth. Commun. 2000, 30, 108.
35. (c) Samajdar, S.; Becker, F. F.; Banik, B. K. Tetrahedron Lett. 2000, 41, 8017.
36. (d) Samajdar, S.; Becker, F. F.; Banik, B. K. Arkivoc 2001, TG-223.
37. (e) Banik, B. K.; Ghatak, A.; Venkatraman, M. S.; Becker, F. F. Synth. Commun. 2000, 30, 2701.
38. (f) Samajdar, S.; Becker, F. F.; Banik, B. K. Synth. Commun. 2002, 32, 1917.
39. Carrigan, M. D.; Sarapa, D.; Smith, R. C.; Wieland, L. C.; Mohan, R. S. J. Org. Chem. 2002, 67, 1027. Also see: Eash, K. J.; Paulia, M. S.; Wieland, L. C.; Mohan, R. S. J. Org. Chem. 2000, 65, 8399.
40. Carrigan, M. D.; Sarapa, D.; Smith, R. C.; Wieland, L. C.; Mohan, R. S. J. Org. Chem. 2002, 67, 1027. Also see: Eash, K. J.; Paulia, M. S.; Wieland, L. C.; Mohan, R. S. J. Org. Chem. 2000, 65, 8399.
41. (a) Wang, Y.-F.; Izawa, T.; Kobayashi, S.; Ohno, M. J. Am. Chem. Soc. 1982, 104, 6465.
42. (b) Hashiguchi, S.; Kawada, A.; Natsugari, H. J. Chem. Soc., Perkin Trans. 1 1991, 2435.
43. (c) Senanayake, C. H.; Fang, K.; Grover, P.; Bakale, R. P.; Vandenbassche, C. P.; Wald, S. A. Tetrahedron Lett. 1999, 40, 819.
44. (d) Genov, M.; Dimitrov, V.; Ivanova, V. Tetrahedron: Asymmetry 1997, 8, 3703.
45. (e) Hayashi, Y.; Rode, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502.
46. (f) Eliel, E. L.; He, X.-C. J. Org. Chem. 1990, 55, 2114.
47. Traxler, P.; Trinks, U.; Buchdunger, E.; Mett, H.; Meyer, T.; Muller, M.; Regenass, U.; Rosel, J.; Lydon, N. J. Med. Chem. 1995, 38, 2441.
48. (a) Bartoli, G.; Cimarelli, C.; Marcantoni E.; Palmieri, G.; Petrinim, M. J. Org. Chem. 1994, 59, 5328.
49. (b) Devine, P. N.; Heid, R. M.; Tschaen, D. M. Tetrahedron 1997, 53, 6739.
50. (c) Graul, A.; Castaner, J.; Castaner, J. Drugs Future 1997, 22, 956.
51. (d) Angiolini, L.; Bizzarri, P. C.; Scapini, G.; Tramontini, M. Tetrahedron 1981, 37, 2137.
52. Arend, M.; Westermann, B.; Risch, N. Angew Chem., Int. Ed. Engl. 1998, 37, 1044.
53. (a) Gomtsyan, A.; Koening, R. J.; Lee, C. H. J. Org. Chem. 2001, 66, 3613.
54. (b) Gomtsyan, A. Org. Lett. 2000, 2, 11.
55. Bartoli, G.; Bosco M.; Marcantoni, E.; Petrinim, M.; Sambri, L.; Torregiani, E. J. Org. Chem. 2001, 66, 9052.
56. Petrini, M.; Profeta, R.; Righi, P. J. Org. Chem. 2002, 67, 4530.
57. (a) Harrington, P. E.; Kerr, M. A. Can. J. Chem. 1998, 76, 1256.
58. (b) Harrington, P. E.; Kerr, M. A. Synlett 1996, 1047.
59. (c) Iqbal, Z.; Jackson, A. H.; Rao, K. R. N. Tetrahedron Lett. 1988, 29, 2577.
60. (d) Szmuszkovicz, J. J. Am. Chem. Soc. 1957, 79, 2819.
61. (a) Houlihan, W. J. Indoles; John Wiley & Sons, Inc.: New York, 1972; Vol. 1, p 71.
62. (b) Iqbal, Z.; Jackson, A. H.; Rao, K. R. Tetrahedron Lett. 1988, 29, 21.