Novel indole chemistry in the synthesis of heterocycles

Current Organic Chemistry

Volumn 9, Issue 15, 2005, Pages 1493-1519

  Gribble, Gordon W ^a   Saulnier, Mark G ^a   Pelkey, Erin T ^a   Kishbaugh, Tara L S ^a   Liu, Yanbing ^a   Jiang, Jun ^a   Trujillo, Hernando A ^a   Keavy, Daniel J ^a   Davis, Deborah A ^a   Conway, Sam C ^a   Switzer, Frank L ^a   Roy, Sujata ^a   Silva, Richard A ^a   Obaza Nutaitis, Judy A ^a   Sibi, Mukund P ^a   Moskalev, Nikolai V ^a   Barden, Timothy C ^a   Chang, Loius ^a   Habeski, Wendy M ^a   Pelcman, Benjamin ^a   Sponholtz III, William R ^a   Chau, Ryan W ^a   Allison, Brett D ^a   Garaas, Sarah D ^a   Sinha, Michael S ^a   McGowan, Meredeth A ^a   Reese, Matthew R ^a   Harpp, Karen S ^a   more..

^a DARTMOUTH COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CYCLOADDITION;

3-DIPOLAR CYCLOADDITION; CYCLOADDUCTS; DIELS-ALDER REACTION; EFFICIENT SYNTHESIS; ELECTRON WITHDRAWING GROUP; HETEROCYCLES; NITROINDOLE; NOVEL RING SYSTEM; NUCLEOPHILIC ADDITIONS;

POLYCYCLIC AROMATIC HYDROCARBONS;

2 NITROINDOLE DERIVATIVE; 2,3 DILITHIOINDOLE; 3 NITROINDOLE DERIVATIVE; CARBAZOLE DERIVATIVE; FURO[3,4 B]INDOLE DERIVATIVE; FURO[3,4 B]PYRROLE DERIVATIVE; FUSED CARBON NITROGEN HETEROCYCLE; INDOLE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL STRUCTURE; CYCLOADDITION; DEHYDRATION; DIELS ALDER REACTION; ELECTRON TRANSPORT; METHODOLOGY; ORGANIC CHEMISTRY; OXIDATION REDUCTION REACTION; REVIEW; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 24644488305     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527205774370487     Document Type: Review

References (64)

1. Baeyer, A. Ann. Chem. 1866, 140, 295-296.
2. Erdmann, O. L. J. Prakt. Chem. 1841, 24, 1-18.
3. Baeyer, A. Chem. Ber. 1880, 13, 2254-2263.
4. Sundberg, R. J. The Chemistry of Indoles, Academic Press: New York, 1970.
5. Sundberg, R. J. Indoles, Academic Press: London, 1996.
6. Li, J. J. In Alkaloids: Chemical and Biological Perspectives, Pelletier, S. W. Ed.; Pergamon Press: Amsterdam, 2001; pp. 573-621.
7. Janosik, T.; Bergman, J.; Pelkey, E. T. Prog. Heterocycl. Chem. 2004, 16, 128-155.
8. Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045-1075.
9. Dolby, L. J.; Gribble, G. W. J. Heterocycl. Chem. 1966, 3, 124-125.
10. Dolby, L. J.; Gribble, G. W. J. Org. Chem. 1967, 32, 1391-1398.
11. Dolby, L. J.; Gribble, G. W. Tetrahedron 1968, 24, 6377-6386.
12. Saulnier, M. G.; Gribble, G. W. J. Org. Chem. 1982, 47, 757-761.
13. Gribble, G. W.; Saulnier, M. G. J. Org. Chem. 1983, 48, 607-609.
14. Liu, Y.; Gribble, G. W. Tetrahedron Lett. 2001, 42, 2949-2951.
15. Gribble, G. W.; Liu, Y. Org. Prep. Proc. Int. 2001, 33, 615-619.
16. Liu, Y.; Gribble, G. W. Tetrahedron Lett. 2002, 43, 7135-7137.
17. Liu, Y.; Gribble, G. W. J. Nat. Prod. 2002, 65, 748-749.
18. Gribble, G. W.; Allison, B. D.; Conway, S. C.; Saulnier, M. G. Org. Prep. Proc. Int. 1992, 24, 649-654.
19. Liu, Y.; Gribble, G. W. Tetrahedron Lett. 2000, 41, 8717-8721.
20. Conway, S. C.; Gribble, G. W. Heterocycles 1992, 34, 2095-2108.
21. Berti, G.; Da Settimo, A.; Nannipieri, E. J. Chem. Soc. (C) 1968, 2145-2151.
22. Pelkey, E. T.; Gribble, G. W. Synthesis 1999, 1117-1122.
23. Pelkey, E. T.; Gribble, G. W. Tetrahedron Lett. 1997, 38, 5603-5606.
24. Saulnier, M. G.; Gribble, G. W. J. Org. Chem. 1982, 47, 2810-2812.
25. Tani, K.; Lukin, K.; Eaton, P. E. J. Am. Chem. Soc. 1997, 119, 1476-1477.
26. Jiang, J.; Gribble, G. W. Tetrahedron Lett. 2002, 43, 4115-4117.
27. Roy, S.; Gribble, G. W. Tetrahedron Lett. 2005, 46, 1325-1328.
28. Joule, J. A. Prog. Heterocycl. Chem. 1999, 11, 45-65.
29. Pelkey, E. T.; Barden, T. C.; Gribble, G. W. Tetrahedron Lett. 1999, 40, 7615-7619.
30. Unpublished results from our laboratory.
31. Norton, R. S.; Wells, R. J. J. Am. Chem. Soc. 1982, 104, 3628-3635.
32. For a review of naturally occurring halogenated indoles, see Gribble, G. W. Prog. Heterocycl. Chem. 2003, 15, 58-74.
33. Kishbaugh, T. L. S.; Gribble, G. W. Tetrahedron Lett. 2001, 42, 4783-4785.
34. Wenkert, E.; Moeller, P. D. R.; Piettre, S. R. J. Am. Chem. Soc. 1988, 110, 7188-7194.
35. Biolatto, B.; Kneeteman, M.; Mancini, P. Tetrahedron Lett. 1999, 40, 3343-3346.
36. Biolatto, B.; Kneeteman, M.; Paredes, E.; Mancini, P. M. E. J. Org. Chem. 2001, 66, 3906-3912.
37. Sha, C.-K. Adv. Nitrogen Heterocycles 1996, 2, 147-178.
38. Daly, K.; Nomak, R.; Snyder, J. K. Tetrahedron Lett. 1997, 38, 8611-8614.
39. Pindur, U.; Erfanian-Abdoust, H. Chem. Rev. 1989, 89, 1681-1689.
40. Jeevanandam, A.; Srinivasan, P. D. J. Chem. Soc., Perkin Trans. 1 1995, 2663-2665.
41. Gribble, G. W.; Pelkey, E. T.; Simon, W. M.; Trujillo, H. A. Tetrahedron 2000, 56, 10133-10140.
42. Gribble, G. W.; Keavy, D. J.; Davis, D. A.; Saulnier, M. G.; Pelcman, B.; Barden, T. C.; Sibi, M. P.; Olson, E. R.; BelBruno, J. J. J. Org. Chem. 1992, 57, 5878-5891.
43. Jiang, J.; Gribble, G. W. Synth. Commun. 2002, 32, 2035-2040.
44. Kishbaugh, T. L. S.; Gribble, G. W. Synth. Commun. 2002, 32, 2003-2008.
45. Barton, D. H. R.; Zard, S. Z. J. Chem. Soc., Chem. Commun. 1985, 1098-1100.
46. Barton, D. H. R.; Kervagoret, J.; Zard, S. Z. Tetrahedron 1990, 46, 7587-7598.
47. Pelkey, E. T.; Chang, L.; Gribble, G. W. Chem. Commun. 1996, 1909-1910.
48. Moody, C. J.; Ward, J. G. J. Chem. Soc., Perkin Trans. 1 1984, 2903-2909.
49. Pelkey, E. T.; Gribble, G. W. Chem. Commun. 1997, 1873-1874.
50. For recent reviews of these heterocycles, see (a) Gribble, G. W. In Synthetic Applications of Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products, Padwa, A.; Pearson, W. H., Eds.; John Wiley & Sons: New York, 2002, Vol. 59, pp. 681-754.
51. (b) Gribble, G. W. In Oxazoles: Synthesis, Reactions and Spectroscopy, Part A, Palmer, D.C., Ed.; John Wiley & Sons: New Jersey, 2003, Vol. 60, pp. 473-576.
52. Gribble, G. W.; Sponholtz III, W. R.; Switzer, F. L.; D'Amato, F. J.; Byrn, M. P. Chem. Commun. 1997, 993-994.
53. Gribble, G. W.; Pelkey, E. T.; Switzer, F. L. Synlett 1998, 1061-1062.
54. Simon, W. M.; Trujillo, H. A.; Pelkey, E. T.; Gribble, G. W.; Jasinski, J. P. Acta Cryst. 2000, C56, 461-462.
55. For the reaction of a münchnone with nitroisoxazoles, see Nesi, R.; Giomi, D.; Turchi, S.; Tedschi, P.; Ponticelli, F. Gazz. Chim. Ital. 1993, 123, 633-635.
56. Mo, C.-J.; Shin-Ya, K.; Furihara, Ka.; Furihata, Ke.; Shimazu, A.; Hayakawa, Y.; Seto, H. J. Antibiot. 1990, 43, 1337-1340.
57. Saulnier, M. G.; Gribble, G. W. Tetrahedron Lett. 1983, 24, 5435-5438.
58. Gribble, G. W.; Saulnier, M. G.; Sibi, M. P.; Obaza-Nutaitis, J. A. J. Org. Chem. 1984, 49, 4518-4523.
59. Gribble, G. W.; Saulnier, M. G. J. Chem. Soc., Chem. Commun. 1984, 168-169.
60. Davis, D. A.; Gribble, G. W. Tetrahedron Lett. 1990, 31, 1081-1084.
61. Gribble, G. W.; Silva, R. A.; Saulnier, M. G. Synth. Commun. 1999, 29, 729-747.
62. Gribble, G. W.; Jiang, J.; Liu, Y. J. Org. Chem. 2002, 67, 1001-1003.
63. Jiang, J.; Gribble, G. W. Org. Prep. Proc. Int. 2002, 34, 533-535.
64. Moskalev, N. V.; Gribble, G. W. Tetrahedron Lett. 2002, 43, 197-201.