A new synthesis of pyrroles from nitroalkenes

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 16, 1985, Pages 1098-1100

  Barton, Derek H R ^a   Zard, Samir Z ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049102052     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/c39850001098     Document Type: Article

References (25)

1. D. H. R. Barton, W. B. Motherwell, and S. Zard, Tetrahedron Lett., 1984, 25, 3707.
2. cf, F. Boberg, K-H. Garburg, K. J. Görlich, E. Pipereit, and M. Ruhr, Liebigs Ann. Chem., 1985, 239.
3. R. G. Coombes in ‘Comprehensive Organic Chemistry’, eds. D. H. R. Barton and W. D. Ollis, Pergamon Press, Oxford, 1979, vol. 2, p. 305.
4. D. Seebach, E. W. Colvin, F. Lehr, and T. Weller, Chimia, 1979, 33, 1 and references therein.
5. ‘The Chemistry of the Nitro Group’, ed. H. Feuer, Interscience, New York, 1970.
6. U. Schöllkopf, Angew. Chem., Int. Ed. Engl., 1977, 16, 339 and references therein.
7. D. Hoppe, Angew. Chem., Int. Ed. Engl., 1974, 13, 789 and references therein.
8. A. M. Van Leusen, H. Siderius, B. E. Hoogenboom, and D. Van Leusen, Tetrahedron Lett., 1972, 5337.
9. S. Halazy and P. Magnus, Tetrahedron Lett., 1984, 25, 1421.
10. Nippon SODA Co., Jpn. Kokkai Tokkyo Koho JP5 885 861.
11. Nippon SODA Co., Chem. Abs, 1983, 99, 122293n.
12. D. O. Cheng and E. LeGoff, Tetrahedron Lett., 1977, 1469.
13. D. H. R. Barton, J. D. Elliot, and S. D. Gero, J. Chem. Soc., Perkin Trans. 1, 1982, 2085.
14. J. H. Tumlinson, R. M. Silverstein, J. C. Moser, R. G. Brownlee, and J. M. Ruth, Nature, 1971, 234, 348.
15. P. Sonnet, J. Med. Chem., 1972, 15, 97.
16. See inter alia: B. Frank, Angew. Chem., Int. Ed. Engl., 1982, 21, 343.
17. T. Wollmann and B. Franck, inter alia:, 1984, 23, 226.
18. K. M. Smith, J. A. P. Baptista de Almeida, and W. M. Lewis, J. Chem. Soc., Perkin Trans. 1, 1974, 502.
19. K. M. Smith, Quart. Rev. Chem. Soc., 1971, 25, 31, and references therein.
20. ‘The Porphyrins’, ed. D. Dolphin, Acdemic Press, New York, 1978, vol. IA, and references therein.
21. (1b) is commercially available (Aldrich, Fluka). For the preparation of (1a), (1c), and (1d) see: I. Ugi, V. Fetzer, H. Knupfer, and K. Offermann, Angew. Chem., Int. Ed. Engl., 1965, 4, 472.
22. R. Damico and J. M. Nicholson, J. Org. Chem., 1973, 38, 3057.
23. Y. Osaki, K. Matsumoto, and M. Miyoshi, Agric. Biol. Chem., 1978, 42, 1565.
24. D. H. R. Barton, W. B. Motherwell, and S. Zard, J. Chem. Soc., Chem. Commun., 1982, 551.
25. D. H. R. Barton, W. B. Motherwell, and S. Zard, Bull. Soc. Chim. Fr.(II), 1983, 61.