Allenyl azide cycloaddition chemistry. Synthesis of annelated indoles from 2-(allenyl)phenyl azide substrates

Organic Letters

Volumn 8, Issue 14, 2006, Pages 3113-3116

  Feldman, Ken S ^a   Iyer, Malliga R ^a   Hester II, D Keith ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; INDOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

AZIDES; CATALYSIS; CYCLIZATION; INDOLES; MOLECULAR STRUCTURE;

EID: 33746588216     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061216u     Document Type: Article

References (29)

1. (a) Little, R. D. Chem. Rev. 1986, 86, 875-884.
2. (b) Moore, H. Adv. Strain Org. Chem. 1995, 4, 81-162.
3. (c) Little, R. D. Chem. Rev. 1996, 96, 93-114.
4. (d) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453-6518.
5. (e) Feldman, K. S.; Mareska, D. A. J. Org. Chem. 1999, 64, 5650-5660.
6. (a) Dowd, P. A. Acc. Chem. Res. 1972, 5, 242-248.
7. (b) Berson, J. A. In Diradicals; Borden, W. T., Ed.; Wiley-VCH: New York, 1982; pp 151-194.
8. (c) Allan, A. K.; Carroll, G. L.; Little, R. D. Eur. J. Chem. 1998, 1-12.
9. (a) Bleiholder, R. F.; Shechter, H. J. Am. Chem. Soc. 1968, 90, 2131-2137.
10. (b) Bingham, E. M.; Gilbert, J. C. J. Org. Chem. 1975, 40, 224-228.
11. (c) Quast, H.; Weise Vélez, C. A. Angew. Chem., Int. Ed. Engl. 1978, 17, 213-214.
12. (d) Quast, H.; Fub, A.; Heublein, A. Angew. Chem., Int. Ed. Engl. 1980, 19, 49-50.
13. (e) Barraclough, D.; Moorhouse, N. P.; Onwuyali, E. I.; Scheinmann, F.; Hursthouse, M. B.; Galas, A. M. R. J. Chem. Res., (S) 1984, 102-103.
14. (f) Quast, H.; Meichsner, G. Chem. Ber. 1987, 120, 1049-1058.
15. (g) Quast, H.; Fub, A.; Heublein, A.; Jakobi, H.; Seiferling, B. Chem. Ber. 1991, 124, 2545-2554.
16. (h) Barker, S. J.; Storr, R. C. J. Chem. Soc, Perkin Trans, 1 1990, 485-488.
17. Feldman, K. S.; Iyer, M. R. J. Am. Chem. Soc. 2005, 127, 4590-4591.
18. Konno, T.; Tanikawa, M.; Ishihara, T.; Yamanaka, H. Collect. Czech. Chem. Commun. 2002, 67, 1421-1435.
19. Regás, D.; Afonso, M. M.; Rodríguez, M. L.; Palenzuela, J. A. J. Org. Chem. 2003, 68, 7845-7852.
20. Kashulin, I. A.; Nifant'ev, I. E. J. Org. Chem. 2004, 69, 5476-5479.
21. (a) Shields, T. C.; Billups, W. E.; Lepley, A. R. J. Am. Chem. Soc. 1968, 90, 4749-4751.
22. (b) Roth, W. R.; Schmidt, T. Tetrahedron Lett. 1971, 3639-3642.
23. (c) Kende, A. S.; Riecki, E. E. J. Am. Chem. Soc. 1972, 94, 1397-1399.
24. (d) Billups, W. E.; Leavell, K. H.; Lewis, E. S.; Vanderpool, S. J. Am. Chem. Soc. 1973, 95, 8096-8102.
25. (e) Gilbert, J. C.; Higley, D. P. Tetrahedron Lett. 1973, 2075-2078.
26. (f) Pikulin, S.; Berson, J. A. J. Am. Chem. Soc. 1985, 107, 8274-8276.
27. (g) Shook, C. A.; Romberger, M. L.; Jung, S.-H.; Xiao, M.; Sherbine, J. P.; Zhang, B.; Lin, F.-T.; Cohen, T. J. Am. Chem. Soc. 1993, 115, 10754-10773.
28. (h) Davidson, E. R.; Gajewski, J. J.; Shook, C. A.; Cohen, T. J. Am. Chem. Soc. 1995, 117, 8495-8501.
29. (i) Direct (IR) detection of triplet-4-methylene-2-pentene-1,5-diyl: Maier, G.; Senger, S. J. Am. Chem. Soc. 1997, 119, 5852-5861.