A new synthesis of substituted imidazo[4,5-£]pyridinones by reductive cyclisation of 4-nitro-l//-imidazol-5-yl di-, and tri-carbonyl compounds

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 5, 1999, Pages 629-640

  Tennant, George ^a   Wallis, Christopher J ^b   Weaver, George W ^c  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2242428264     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808202b     Document Type: Article

References (19)

1. Montgomery, and J. A. Secrist, in Comprehensive Ileterocyclic Chemistry, ed. A. R. Katritzky, and C. W. Rees,
2. Pergamon, Oxford, 1984, vol. 5, Section 4.10.4.3. For some recent examples of imidazo[4,5-6]pyridine syntheses see: (a) D. J. Cundy, G. Holan, M. Otaegui, and G. W. Simpson, Bioorg. Med. Client. Lett., 1997, 7, 669;
3. (b) K. I Khanna, R. M. Weier, K. T. Lentz, L. Swenton, and D. C. Lankin, J. Org. Cliem., 1995, 60, 960;
4. S. Grivas, and S. Lindstroem, J. Hetcrocycl. Cliem., 1995, 32, 467.
5. (a) G. Cristalli, S. Vittori, A. Eleuteri, R. Volpini, E, Camaioni, G. Lupidi, N. Mahmood, F. Bevilacqua, and G. Palu, J. Med. Client., 1995, 38, 4019;
6. (b) G. Cristalli, P. Franchetti, M. Grifantini, S. Vittori, T. Bordoni, and C. Geroni, J. Med. Cliem., 1987,30, 1686.
7. (a) G. Cristalli, A. Eleuteri, S. Vittori, R. Volpini, M. J. Lohse, and K.-N. Kotz, J. Med. Client., 1992, 35, 2363;
8. (b) G. Cristalli, P. Franchetti, M. Grifantini, S. Vittori, K.-N. Klotz, and M. J. Lohse, J. Med. Client., 1988,31, 1179.
9. F. Perandones, and J. L. Solo, J. Heterocycl. Client., 1997, 34, 107.
10. J. Sarasin, and E. Wegmann, Heir. Cliim. Acta, 1924, 7, 713.
11. For a review on the neighbouring group reactivity of the nitro group see P. N. Preston, and G. Tennant, Cliem. Rev., 1972,72, 627.
12. F. G. Mann, and J. W. G. Porter, J. Cliem. Soc., 1945, 751.
13. J. Sarasin, and E. Wegman, I/elv. Chim. Acta, 1924,7, 720.
14. M. Petrini, R. Battini, and G. Rosini, Synthesis, 1987, 713. For the reduction of nitro compounds using borohydride in the presence of other metals see: (a) J. A. Cowan, Tetrahedron Lett., 1986, 27, 1205;
15. (b) J. O. Osby, and B. Ganem, Tetrahedron Lett., 1985, 26, 6413.
16. A. Obregia, Liebigs Ann. Client., 1891, 266, 324.
17. G. Tennant, C. J. Wallis, and G. W. Weaver, J. Client. Soc., Perkin Trans. I, in the press.
18. G. Beck, and D. Günther, Client. Ber., 1973,106, 2758.
19. O. Isler, H. Gutmann, M. Montavon, R. Rüega, G. Ryser, and P. Zeller, Heir. Chim. Acta, 1957, 40, 1242.