Synthesis of five-membered lactams by α-carbamoyl radical cyclisations

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 5, 1989, Pages 879-886

  Sato, Tatsunori ^a   Wada, Yasuko ^a   Nishimoto, Mami ^a   Ishibashi, Hiroyuki ^a   Ikeda, Masazumi ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049080528     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19890000879     Document Type: Article

References (33)

1. D. J. Hart and Y. -M. Tsai, J. Am. Chem. Soc., 1982, 104, 1430.
2. D. A. Burnett, J. -K. Choi, D. J. Hart, and Y. -M. Tsai, J. Org. Chem., 1984, 106, 8201.
3. D. J. Hart and Y. -M. Tsai, J. Org. Chem., p. 8209.
4. J. -K. Choi and D. J. Hart, Tetrahedron., 1985, 41, 3959.
5. G. E. Keck and E. J. Enholm, Tetrahedron Lett., 1985, 26, 3311.
6. S. Kano, Y. Yuasa, K. Asami, and S. Shibuya, Chem. Lett., 1986, 735.
7. M. D. Bachi, A. De Mesmaeker, and N. Stevenart-De Mesmaeker, Tetrahedron Lett., 1987, 28, 2887.
8. A. Padwa, H. Nimmesgern, and G. S. K. Wong, J. Org. Chem., 1985, 50, 5620.
9. Y. Ueno, C. Tanaka, and M. Okawara, Chem. Lett., 1983, 795.
10. S. J. Danishefsky and J. S. Panek, J. Am. Chem. Soc., 1987, 109, 917.
11. J. Knight and P. J. Parsons, J. Chem. Soc., Perkin Trans. 1., 1987, 1237.
12. Y. Watanabe, Y. Ueno, C. Tanaka, M. Okawara, and T. Endo, Tetrahedron Lett., 1987, 28, 3953.
13. Metal-catalysed cyclisations of α-halogeno-N-allylacetamides giving five-membered lactams have been reported. See H. Nagashima, K. Ara, H. Wakamatsu, and K. Ito, J. Chem. Soc., Chem. Commun., 1985, 518.
14. M. Mori, N. Kanda, I. Oda, and Y. Ban, Tetrahedron., 1985, 41, 5465.
15. C. K. Tseng, E. G. Teach, and R. W. Simons, Synth. Commun., 1984, 14, 1027.
16. For a preliminary account of a portion of this work, see H. Ishibashi, T. Sato, M. Irie, S. Harada, and M. Ikeda, Chem. Lett., 1987, 795.
17. For an aromatic radical cyclisation, see J. J. Köhler and W. N. Speckamp, Tetrahedron Lett., 1977, 631.
18. B. B. Snider and M. A. Dombroski, J. Org. Chem., 1987, 52, 5487.
19. H. G. Viehe, R. Merényi, L. Stella, and Z. Janousek, Angew. Chem., Int. Ed. Engl., 1979, 18, 917.
20. Y. Ueno, R. K. Khare, and M. Okawara, J. Chem. Soc., Perkin Trans. 1., 1983, 2637.
21. A. L. J. Beckwith, C. J. Easton, and A. K. Serelis, J. Chem. Soc., Chem. Commun., 1980, 482.
22. M. A. M. Bradney, A. D. Forbes, and J. Wood, J. Chem. Soc., Perkin Trans. 2., 1973, 1655.
23. A. L. J. Beckwith, Tetrahedron., 1981, 37, 3073.
24. A. L. J. Beckwith and C. H. Schiesser, Tetrahedron., 1985, 41, 3925.
25. H. Ishibashi, M. Ikeda, H. Maeda, K. Ishiyama, M. Yoshida, S. Akai, and Y. Tamura, J. Chem. Soc., Perkin Trans. 1., 1987, 1099.
26. A. Mooradian, C. J. Cavallito, A. J. Bergman, E. J. Lawson, and A. W. Suter, J. Am. Chem. Soc., 1949, 71, 3372.
27. Y. Tamura, J. Uenishi, H. Maeda, H. -D. Choi, and H. Ishibashi, Synthesis., 1981, 534.
28. H. Ishibashi, M. Okada, K. Sato, M. Ikeda, K. Ishiyama, and Y. Tamura, Chem. Pharm. Bull., 1985, 33, 90.
29. N. F. Cywinski, U. S. P. 3 821 298/1974 (Chem. Abstr., 1974, 81, P90642k).
30. I. N. Tyurenkov, V. V. Perekalin, G. V. Kovalev, I. S. Morozov, V. S. Grineva, and I. N. Kiseleva, Tr. Volgogr. Gos. Med. Inst., 1979, 31, 35 (Chem. Abstr., 1981, 95, 143835y).
31. M. -M. Lay and J. E. Casida, Pestic. Biochem. Physiol., 1976, 6, 442 (Chem. Abstr., 1976, 85, 187439v).
32. R. Brehme and P. Thelen, J. Prakt. Chem., 1981, 323, 299.
33. A. Meller, F. J. Hirninger, M. Noltemeyer, and W. Maringgele, Chem. Ber., 1981, 114, 2519.