Synthesis of 2-nitroindoles via the Sundberg indole synthesis

Tetrahedron Letters

Volumn 38, Issue 32, 1997, Pages 5603-5606

  Pelkey, Erin T ^a   Gribble, Gordon W ^a  

^a Dartmouth College   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 NITROINDOLE DERIVATIVE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; TEMPERATURE; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0030795077     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01272-0     Document Type: Article

References (20)

1. Pelkey, E.T.; Chang, L.; Gribble, G.W. J. Chem. Soc., Chem. Commun. 1996, 1909.
2. 3-Nitroindole: Berti, G.; Da Settimo, A.; Nannipieri, E. J. Chem. Soc. C 1968, 2145.
3. 4-Nitroindole: Kato, K.; Ono, M.; Akita, H. Tetrahedron Lett. 1997, 38, 1805.
4. 5-Nitroindole: Kasahara, A.; Izumi, T.; Kikuchi, T.; Xiao-Ping, L. J. Heterocycl. Chem. 1987, 24, 1555.
5. 6-Nitroindole: Melhado, L.L.; Leonard, N.J. J. Org. Chem. 1983, 48, 5130.
6. 7-Nitroindole: Somei, M.; Yamada, F.; Hamada, H.; Kawasaki, T. Heterocycles 1989, 29, 643.
7. Russell, G.A.; Yao, C.-F.; Tashtoush, H.I.; Russell, J.E.; Dedolph, D.F. J. Org. Chem. 1991, 56, 663.
8. For a leading reference, see: Saulnier, M.G.; Gribble, G.W. J. Org. Chem. 1982, 47, 757.
9. Lukin, K.; Li, J.; Gilardi, R.; Eaton, P.E. Angew. Chem. Int. Ed. Engl. 1996, 35, 864.
10. Sundberg, R.J.; Russell, H.F.; Ligon, W.V.; Lin, L.-S. J. Org. Chem. 1980, 45, 4767.
11. Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254.
12. Dickson, N.J.; Dyall, L.K. Aust. J. Chem. 1980, 33, 91.
13. Molina, P.; Conesa, C.; Alias, A.; Arques, A.; Velasco, M.D.; Llamas-Saiz, A.L.; Foces-Foces, C. Tetrahedron 1993, 49, 7599.
14. Caution: azidostyrene 10 is a strong skin and eye irritant.
15. 2: C, 59.26; H, 3.73; N, 17.28. Found: C, 59.36; H, 3.79; N, 17.21.
16. Kumar, S.; Wachlel, E.J.; Keinan, E. J. Org. Chem. 1993, 58, 3821.
17. 4: C, 54.05; H, 4.56; N, 12.45. Found: C, 53.95; H, 4.54; N, 12.61.
18. 4S: C, 55.62; H, 3.33; N, 9.27; S, 10.61. Found: C, 55.58; H, 3.35; N, 9.22; S, 10.70.
19. Gribble, G.W.; Barden, T. B. unpublished results.
20. For a recent example and leading reference, see: Cooper, M.M.; Lovell, J.M.; Joule, J.A. Tetrahedron Lett. 1996, 37, 4283.