Reactions of 2-methyl-3,1-benzoxazin-4-one with active methylene compounds: A new route to 3-substituted 4-hydroxyquinolin-2(1H)-ones

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 24, 1996, Pages 2909-2913

  Detsi, Anastasia ^a   Bardakos, Vassilios ^a   Markopoulos, John ^b   Igglessi Markopoulou, Olga ^a  

^a NATIONAL TECHNICAL UNIVERSITY OF ATHENS   (Greece)

^b UNIVERSITY OF ATHENS   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748916262     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960002909     Document Type: Article

References (33)

1. (a) A. M. MacLeod, S. Grimwood, C. Barton, L. Bristow, K. Saywell, G. R. Marshall and R. G. Ball, J. Med. Chem., 1995, 38, 2239;
2. (b) R. W. Carling, P. D. Leeson, K. W. Moore, J. D. Smith, C. R. Moyes, I. M. Mawer, S. Thomas, T. Chan, R. Baker, A. C. Foster, S. Grimwood, J. A. Kemp, G. R Marshall, M. T. Tricklebank and K. L. Saywell, J. Med. Chem., 1993, 36, 3397;
3. (c) M. Rowley, P. D. Leeson, G. I. Stevenson, A. M. Moseley, I. Stansfield, I. Sanderson, L. Robinson, R. Baker, J. A. Kemp, G. R. Marshall, A. C. Foster, S. Grimwood, M. D. Tricklebank and K. L. Saywell, J. Med. Chem., 1993, 36, 3386.
4. I. V. Ukrainets, S. G. Taran, P. A. Bezuglyi, S. N. Kovalenko, A. V. Turov and N. A. Marusenko, Khim. Geterotsikl. Soedin., 1993 (9), 1223.
5. C. F. Neville, M. F. Grundon, V. N. Ramachandran, G. Reisch and J. Reisch, J. Chem. Soc., Perkin Trans. 1, 1991, 2261.
6. H. Hayashi, Y. Miwa, S. Ichikawa, N. Yoda, I. Miki, A. Ishi, M. Kono, T. Yasusawa and F. Suzuki, J. Med. Chem., 1993, 36, 617.
7. P. D. Leeson, R. Baker, R. W. Carling, J. J. Kulagowski, I. M. Mawer, M. P. Ridgill, M. Rowley, J. D. Smith, I. Stansfield, G. I. Stevenson, A. C. Foster and J. A. Kemp, Bioorg. and Med. Chem. Lett., 1993, 3(2), 299.
8. J. J. Kugalowski, R. Baker, N. R. Curtis, P. D. Leeson, I. M. Mawer, A. M. Moseley, M. P. Ridgill, M. Rowley, I. Stansfield, A. C. Foster, S. Grimwood, R. G. Hill, J. A. Kemp, G. R. Marshall, K. L. Saywell and M. D. Tricklebank, J. Med. Chem., 1994, 37, 1402.
9. R. N. Lacey, J. Chem. Soc., 1954, 850.
10. (a) I. V. Ukrainets, P. A. Bezuglyi, V. I. Treskach and A. V. Turov, Khim. Geterotsikl. Soedin., 1992 (5), 538;
11. (b) I. V. Ukrainets, P. A. Bezuglyi, V. I. Treskach, A. V. Turov and S. V. Slobodzyan, Khim. Geterotsikl. Soedin., 1992 (5), 636;
12. (c) E. Ziegler, H. Junek and A. Metallidis, Monatsh. Chem., 1970, 101, 92.
13. (a) T. Kappe, A. S. Karem and W. Stadlbauer, J. Heterocycl. Chem., 1988, 25, 857;
14. (b) R. Laschober and W. Stadlbauer, Liebigs Ann. Chem., 1990, 11, 1083;
15. (c) W. Stadlbauer, R. Laschober, H. Lutschounig and T. Kappe, Monatch. Chem., 1992, 123, 617.
16. (a) G. M. Coppola and G. E. Hardtmann, J. Heterocycl. Chem., 1979, 16, 1605;
17. (b) G. M. Coppola, J. Heterocycl. Chem., 1983, 20 (5), 1217.
18. (a) P. Bravo, G. Resnati, F. Viani and G. Cavicchio, J. Chem. Res. (S), 1986, 374;
19. (b) E. Pongratz and T. Kappe, Monatsh. Chem., 1984, 115, 231;
20. (c) P. Roschger, W. Fiala and W. Stadlbauer, J. Heterocycl. Chem., 1992, 29, 225.
21. (a) O. Igglessi-Markopoulou and C. Sandris, J. Heterocycl. Chem., 1982, 19, 883;
22. (b) O. Igglessi-Markopoulou and C. Sandris, J. Heterocycl. Chem., 1985, 22, 1599;
23. (c) O. Markopoulou, J. Markopoulos and D. Nicholls, J. Inorg. Biochem., 1990, 39, 307;
24. (d) J. V. Barkley, J. Markopoulos and O. Markopoulou, J. Chem. Soc., Perkin Trans. 2, 1994, 1271;
25. (e) A. Detsi, J. Markopoulos and O. Igglessi-Markopoulou, J. Chem. Soc., Chem. Commun., 1996, 1323.
26. G. K. Helmkamp and H. W. Johnson Jr, Selected Experiments in Organic Chemistry, W. H. Freeman and Company, San Francisco and London, 2nd edn. 1968, p. 155.
27. (a) J. Vicens, M. C. Etter and L. A. Errede, Tetrahedron Lett., 1983, 24 (7), 723;
28. (b) A. Williams and G. Salvadori, J. Chem. Soc. (B), 1971, 1105.
29. K. Nakanihsi and P. H. Solomon, Infrared Absorption Spectroscopy, Holden-Day Inc., 2nd edn., 1977.
30. G. M. Coppola, A. D. Kahle and M. J. Shapiro, Org. Magn. Reson., 1981, 17 (4), 242.
31. José Luis Garcia Ruano, Concepcion Pedregal and Jésus H. Rodriguez, Heterocycles, 1991, 32 (11), 2151.
32. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902.
33. C. M. Foltz and Y. Kondo, Tetrahedron Lett., 1970, 36, 3163.