New findings in hetero Diels-Alder reactions of quinolinetriones

Tetrahedron

Volumn 52, Issue 16, 1996, Pages 5933-5944

  Blanco, Ma Del Mar ^a   Alonso, Miguel Ángel ^a   Avendaño, Carmen ^a   Menéndez, J Carlos ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

FURO[2,3 F]QUINOLINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

BETULACEAE;

EID: 0000745912     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00224-4     Document Type: Article

References (42)

1. a) Boger, D. L. Tetrahedron 1983, 39, 2869-2939.
2. b) Boger, D. L. Chem. Rev. 1986, 86, 781-793.
3. c) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis. Academic Press, 1987.
4. d) Boger, D. L.; Patel, M. Progress Heterocycl. Chem. 1989, 1, 31.
5. e) Boger, D. L. in Paquette, L. A. (ed.), Comprehensive Organic Synthesis, vol. 5, p. 451 (Trost, B. M. and Fleming, I. general editors). Pergamon Press, 1991.
6. Barluenga, J. and Tomás, M. Adv. Heterocycl. Chem. 1993, 57, 1.
7. Kametani, T.; Hibino, S. Adv. Heterocycl. Chem. 1987, 42, 246.
8. Tietze, L. F. J. Heterocycl. Chem. 1990, 27, 47.
9. a) Weinreb, S. M.; Scola, P. M. Chem. Rev. 1989, 89, 1525.
10. b) e) Weinreb, S. M. in Paquette, L. A. (ed.), Comprehensive Organic Synthesis, vol. 5, p. 401 (Trost, B. M. and Fleming, I. general editors). Pergamon Press, 1991.
11. a) Serckx-Poncin, B.; Hesbain-Frisque, A.-M.; Ghosez, L. Tetrahedron Lett. 1982, 23, 3261.
12. b) Ghosez, L.; Serckx-Poncin, B.; Rivera, M.; Bayard, P.; Sainte, F. Demoulin, A.; Hesbain-Frisque, A.-M.; Mockel, A.; Muñoz, L.; Bernard-Henriet, C. Lect. Heterocycl. Chem. 1985, 8, 69.
13. For reviews on the chemistry and some biological aspects of heterocyclic quinones, see: a) Middleton, R. W. and Parridge, J. In Patai, S. and Rappoport, Z. (eds.), The Chemistry of the Quinonoid Compounds, vol. 2, p. 1019. John Wiley and Sons, 1988.
14. b) Thomson, R. H. In ApSimon, J. (ed.), The Total Synthesis of Natural Products, vol. 8, p. 312. Academic Press, 1992.
15. c) Itoh, S. and Ohshiro, Y. Nat. Prod. Rep., 1995, 12, 45.
16. a) Bracher, F. Liebigs Ann. Chem. 1989, 87-88.
17. b) Gómez-Bengoa, E.; Echavarren, A. M. J. Org. Chem. 1991, 56, 3497.
18. a) Potts, K. T.; Walsh, E. B.; Bhattacharjee, D. J. Org. Chem. 1987, 52, 2285.
19. b) Kitahara, Y. and Kubo, A. Heterocycles 1992, 34, 1089.
20. Behforouz, M.; Gu, Z.; Cai, W.; Horn, M. A.; Ahmadiam, M. J. Org. Chem. 1993, 58, 7089.
21. a) J. M. Pérez, C. Avendaño, J. C. Menéndez, Tetrahedron 1995, 51, 6573. For biological data, see:
22. b) Gesto, C., de la Cuesta, E., Avendaño, C.; Emling, F., J. Pharm. Sci., 1992, 81, 815.
23. c) Avendaño, C.; Alonso, M. A.; Espada, M.; García-Grávalos, D.; Menéndez, J. C.; Ocaña, B.; Pérez, J. M., Eur. Pat. Appl. EP 574,195 (15-12-93). Chem. Abstr., 1994, 120, 270358e.
24. a) Pettit, G. R.; Fleming, W. C.; Paull, K. D. J. Org. Chem. 1968, 33, 1089.
25. b) Avendaño, C.; de la Cuesta, E.; Gesto, C. Synthesis 1991, 727.
26. c) Blanco, M. M.; Avendaño, C.; Cabezas, N.; Menéndez, J. C. Heterocycles, 1993, 36, 1387.
27. d) Alonso, M. A.; Blanco, M. M.; Avendaño, C.; Menéndez, J. C. Heterocycles, 1993, 36, 2315.
28. e) Kitahara, Y.; Nakahara, S.; Shimizu, M.; Yozenawa, T.; Kubo, A. Heterocycles 1993, 36, 1909.
29. f) Martín, O.; de la Cuesta, E.; Avendaño, C. Tetrahedron 1995, 51, 7547.
30. a) Omura, S.; Iwai, Y.; Hinotozawa, K.; Tanaka, H.; Takahashi, Y.; Nakagawa, A. J. Antibiotics 1982, 35, 1425.
31. b) Tsuzuki, K.; Yokozuka, T.; Murata, M.; Tanaka, H.; Omura, S. J. Antibiotics 1989, 42, 727.
32. Other workers have noticed similar problems associated with the use of 1-dimethylamino-1-azadienes in Diels-Alder chemistry. See, for example, reference 9a and: Nebois, P.; Cherkaoui, L.; Fillion, H. Tetrahedron 1994, 50, 8457.
33. Waldner, A. Helv. Chim. Acta, 1988, 71, 486.
34. M. M. Blanco, J. M. Pérez, C. Avendaño, J. C. Menéndez, unpublished results.
35. Hegedus, L. S.; Sestrick, M. R.; Michaelson, E. T.; Harrington, P. J., J. Org. Chem., 1989, 54, 4141.
36. Nebois, P. and Fillion, H., Tetrahedron Lett, 1991, 32, 1307.
37. Valderrama, J. A. and González, M. F. Heterocycles , 1993, 36, 1553.
38. Echavarren, A. M., J. Org. Chem. 1990, 55, 4255.
39. Nebois, P.; Fillion, H; Benameur, L., Tetrahedron, 1993, 49, 9767.
40. Tanoue, Y. and Terada, A., Bull. Chem. Soc. Jpn., 1988, 61, 2039.
41. Cerium (III) derivatives are well-known Lewis acids. See, for example: a) Molander, G. A., Chem. Rev., 1992, 92, 29.
42. b) Imamoto, T., Lanthanides in Organic Synthesis, chapter 5. Academic Press, 1994.