Vinyl isonitriles in radical cascade reactions: Formation of cyclopenta-fused pyridines and pyrazines

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 5, 2000, Pages 641-643

  Lenoir, Isabelle ^a   Smith, Marie L ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

FREE RADICALS; IRRADIATION; POLYMERIZATION; X RAY ANALYSIS;

RADICAL CASCADE REACTIONS;

AROMATIC COMPOUNDS;

EID: 0034615526     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908630g     Document Type: Article

References (25)

1. See for example: C. K. Sha, F. K. Lee and C. J. Chang, J. Am. Chem. Soc., 1999, 121, 9875;
2. M. Kizil, B. Patro, O. Callaghan, J. A. Murphy, H. B. Hursthouse and D. Hibbs, J. Org. Chem., 1999, 64, 7856;
3. F. Belval, A. Fruchier, C, Chavis, J. L. Montera and M. Lucas, J. Chem. Soc., Perkin Trans. 1, 1999, 697;
4. S. R. Baker, K. I. Burton, A. F. Parsons, J. F. Pons and M. Wilson, J. Chem. Soc., Perkin Trans. 1, 1999, 427,
5. S. A. Hitchcock, S. J. Houldsworth, G. Pattenden, D. C. Pryde and N. M. Thomson, J. Chem. Soc., Perkin Trans. 1., 1998, 3181.
6. D. P. Curran and H. Liu, J. Am. Chem. Soc., 1991, 113, 2127;
7. I. Ryu, N. Sonoda and D. P. Curran, Chem. Rev., 1996, 96, 177.
8. (a) C. M. Camaggi, R. Leardini, D. Nanni and G. Zanardi, Tetrahedron, 1998, 54, 5587;
9. (b) D. Nanni, P. Pareschi, C. Rizzoli, P. Sgarabotto and A. Tundo, Tetrahedron, 1995, 51, 9045.
10. D. P. Curran, H. Liu, H. Josien and S.-B. Ko, Tetrahedron, 1996, 52, 11385;
11. H. Josien, D. Bom and D. P. Curran, Bioorg. Afed. Chem. Lett., 1997, 24, 3189;
12. H. Josien and D. P. Curran, Tetrahedron, 1997, 53, 8881;
13. D. P. Curran, H. Josien and S.-B. Ko, Angew. Chem., Int. Ed. Eng!., 1995, 34, 2683;
14. D. P. Curran and H. Liu, J. Am. Chem. Soc., 1992, 114, 5863.
15. J. E. Baldwin and I. A. O'Neil, Synlett, 1990, 603.
16. J. E. Baldwin, D. J. Aldous, C. Chan, L. M. Harwood, I. A. O'Neil and J. M. Peach, Synlett, 1989, 9.
17. D. H. R. Barton, T. Bowles, S. Husinec, J. E. Forbes, A. Llobera, A. E. A. Porter and S. Z. Zard, Tetrahedron Lett., 1988, 29, 3343.
18. For the application of vinyl isonitriles in Ugi 4-component condensations see: T. A. Keating and R. W. Armstrong, J. Am. Chem. Soc., 1996, 118, 2574.
19. For the use of alkyl isonitriles in synthesis see: G. Stork and P. M. Sher, J. Am. Chem. Soc., 1983, 105, 6765.
20. P. Dovvd and S.-C. Choi, Tetrahedron, 1989, 45, 77;
21. A. L. J. Beckwith, D. M. O'Shea and S. W. Westwood, J. Am. Chem. Soc., 1988, 110, 2565.
22. M. Barbier, D. H. R. Barton, M. Devys and R. S. Topgi, J. Chem. Soc., Chem. Commun., 1984, 743.
23. R. Leardini, D. Nanni, G. F. Pedulli, A. Tundo and G. Zanardi, J. Chem. Soc., Perkin Trans. 1, 1986, 1591.
24. W. R. Bowman, H. Heaney and B. M.Jordan, Tetrahedron, 1991, 47, 10119;
25. D. Crich and J.-H. Hwang, J. Org. Chem., 1998, 63, 2765.