Ready access to 7,8-dihydro- and 1,2,3,4-tetrahydro-1,6-naphthyridine-5(6H) -ones from simple pyridine precursors

Journal of Heterocyclic Chemistry

Volumn 43, Issue 5, 2006, Pages 1311-1317

  Showalter, H D Hollis ^a,b  

^a PFIZER INC   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4 TETRAHYDRO 1 METHYL 1,6 NAPHTHYRIDINE 5(6H) ONE; 1,2,3,4 TETRAHYDRO 1,6 NAPHTHYRIDINE 5(6H) ONE; 1,6 NAPHTHYRIDIN 5 ONE DERIVATIVE; 1,6 NAPHTHYRIDINE 5(6H) ONE; 2 [2 (5 OXO 7,8 DIHYDRO 5H 1,6 NAPHTHYRIDIN 6 YL)ETHYL] 3 PYRIDINECARBOXYLIC ACID; 2 METHYLNICOTINAMIDE; 4 BROMO 1 CHLORO 1,6 NAPHTHYRIDINE; 4 BROMO 1 METHOXY 1,6 NAPHTHYRIDINE; 5,6,7,8 TETRAHYDRO 1 METHYL 5 OXO 1,6 NAPHTHYRIDINIUM IODIDE; 7 METHYL 1,6 NAPHTHYRIDINE 5(6H) ONE; 7,8 DIHYDRO 1,6 NAPHTHYRIDIN 5(6H)ONE; 7,8 DIHYDRO 5H PYRANO[4,3 B]PYRIDIN 5 ONE; 8 BROMO 1,6 NAPHTHYRIDINE 5(6H) ONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 33750933092     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570430525     Document Type: Article

References (27)

1. R. W. Pero, A. Olsson, H. Lindgren, and T. Leanderson In: PARP as a Therapeutic Target, J. Zhang, Ed.; CRC Press LLC: Boca Raton, 2002; pp 205-221.
2. [2a] S. Peukert, U. Schwahn, S. Guessregen, H. Schleuder and A. Hofmeister, Synthesis 1550 (2005);
3. [b] R. J. Griffin, L. C. Pemberton, D. Rhodes, C. Bleasdale, K. Bowman, A. H. Calvert, N. J. Curtin, B. W. Durkacz, D. R. Newell, J. K. Porteous and B. T. Golding, Anti-Cancer Drug Design, 10, 507 (1995).
4. Recent reviews on PARP-1 inhibitors include; [c] S. Peukert and U. Schwahn, Exp. Opin. Therapeut. Pat., 14, 1531 (2004);
5. [d] E. C. Y. Woon and M. D. Threadgill, Curr. Med. Chem., 12, 2373 (2005).
6. M. J. Suto, W. R. Turner, C. M. Arundel-Suto, L. M. Werbel and J. Sebolt-Leopold, Anti-Cancer Drug Design, 6, 107 (1991).
7. [4a] V. I. Sigova and M. E. Konshin, Khim. Geterotsikl. Soedin., 783 (1984);
8. [b] K. H. Nietsch, R. Troschuetz and H. J. Roth, Arch. Pharm. (Weinheim), 318, 175 (1985).
9. [5a] Y. Combret, J.-J. Torche, P. Binay, G. Dupas, J. Bourguignon and G. Quenguiner, Chem. Lett., 125 (1991);
10. [b] Y. Combret, J.-J. Torche, N. Ple, J. Duflos, G. Dupas, J. Bourguignon and G. Queguiner, Tetrahedron, 47, 9369 (1991);
11. [c] Y. Combret, J. Duflos, G. Dupas, J. Bourguignon and G. Queguiner, G. Tetrahedron: Asymmetry, 4, 1635 (1993).
12. [6a] H. Takahata, T. Suzuki and T. Yamazaki, Heterocycles, 24, 1247 (1986);
13. [b] N. Ikekawa, Chem. Pharm. Bull., 6, 263, (1958).
14. [7a] C. Vitry, J. Bedat, Y. Prigent, V. Levacher, G. Dupas, I. Salliot, G. Queguiner and J. Bourguignon, Tetrahedron, 57, 9101 (2001);
15. [b] J. Kleinschroth, K. Mannhardt, J. Hartenstein and G. Satzinger, Synthesis, 859 (1986).
16. H. D. H. Showalter, United States Patent 5,391,554 (1995).
17. J. S. New, J. P. Yevich, D. L. Temple, Jr., K. B. New, S. M. Gross, R. F. Schlemmer, Jr., M. S. Eison, D. P. Taylor, and L. A. Riblet, J. Med. Chem., 31, 618 (1988).
18. I. A. Cliffe, A. D. Ifill, H. L. Mansell, R. S. Todd and A. C. White, Tet. Lett., 32, 6789 (1991). Further confirmation of the aza-Michael mechanism was supported by brief investigations into the attempted formation of 4 from the carboxamide of 3. Heating solutions of this in a number of common solvents failed to provide 4.
19. I. K. Khanna, Y. Yu, R. M. Huff, R. M. Weier, X. Xu, F. J. Koszyk, P. W. Collins, J. N. Cogbum, P. C. Isakson, C. M. Koboldt, J. L. Masferrer, W. E. Perkins, K. Seibert, A. W. Veenhuizen, J. Yuan, D.-C. Yang and Y. Y. Zhang, J. Med. Chem., 43, 3168 (2000).
20. P. E. Mareki, J. M. Wemple and G. P. Butke, J. Heterocycl. Chem., 19, 1247 (1982).
21. J. J. Baldwin, K. Mensler and G. S. Ponticello, J. Org. Chem., 43, 4878 (1978). Baldwin's procedure is similar to ours shown in Scheme 2, but requires that initial condensation of N,N-dimethylformamide dimethyl acetal occur on the 2-methyl function of 2-methylnicotinonitrile substrate. Subsequent cyclization of the resultant enamine with hydrogen bromide gave 10a in 46% overall yield, along with 15% of a brominated side product
22. D. E. Ames and W. D. Dodds, J. Chem. Soc., Perkin Trans. 1: Org. & Bio-Org. Chem. (1972-1999), 705 (1972).
23. G. Paglietti, P. Sanna, A. Nuvole, F. Soccolini and R. M. Acheson, J. Chem. Res., Synopses, 245 (1983).
24. M. Lounasmaa, P. Juutinen and P. Kairisalo, Tetrahedron, 34, 2529 (1978).
25. E. Booker and U. Eisner, J. Chem. Soc., Perkin Trans. 1: Org. & Bio-Org. Chem. (1972-1999), 929 (1975).
26. Y. Shizuta, S. Ito, K. Nakata and O. Hayaishi, Methods Enzymol., 66, 159 (1980).
27. H. D. H. Showalter, W. L. Elliott and J. S. Sebolt-Leopold, Proc. Am. Assoc. Cancer Res., 34, 266 (1993) (Abstract 1583).