Synthesis of 4-phenylquinoline-5,8-quinones and their reactivity in hetero Diels-Alder reactions

Synthesis

Volumn , Issue 8, 1999, Pages 1335-1340

  Úbeda, J Ignacio ^a   Villacampa, Mercedes ^a   Avendaño, Carmen ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

4 arylquinolines; Azaanthraquinones; Diels alder reaction; Friedlander reaction; Pivaloylaniline

Indexed keywords

ACETIC ACID; PHENYL GROUP; QUINOLINE DERIVATIVE; QUINONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032871545     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3549     Document Type: Article

References (25)

1. See for instance: (a) Potts, K. T.; Walsh, E. B.; Bhattacharjee, D. J. Org. Chem. 1987, 52, 2285.
2. (b) Waldner, A. Helv. Chim. Acta 1988, 71, 486 and 493.
3. (c) Dolle, R. E.; Armstrong, W.; Shaw, A. N.; Novelli, R. Tetrahedron Lett. 1988, 29, 6349.
4. (d) Gesto, C., de la Cuesta, E.; Avendaño, C. Tetrahedron 1989, 45, 4477.
5. (e) Nebois, P.; Fillion, H. Tetrahedron Lett. 1991, 32, 1307.
6. (f) Bracher, F. Liebigs Ann. Chem. 1992, 1205.
7. (g) Chaker, L.; Pautet, F.; Fillion, H. Heterocycles 1995, 41, 1169.
8. (a) Perumal, P. J.; Bahtt, M. V.; Synthesis 1979, 205.
9. (b) Brimble, M. A.; Brimble, M. T.; Gibson, J. J.; J. Chem. Soc., Perkin Trans. I 1989, 179.
10. (c) Echavarren, A. M. J. Org. Chem. 1990, 55, 4255.
11. (a) Pérez, J. M.; Avendaño, C.; Menéndez, J. C. Tetrahedron 1995, 51, 6573.
12. (b) Avendaño, C.; Blanco, M. M.; Menéndez, J. C.; García-Grávalos, D.; Fernández-Puentes, J. L. U K Patent Appl. 9 708 751.4 (1997).
13. Chigr, M.; Fillion, H.; Rougny, A. Tetrahedron Lett. 1988, 29, 5913.
14. Kitahara, Y.; Tamura, F.; Kubo, A.; Chem. Pharm. Bull. 1994, 42, 1363.
15. Gómez-Bengoa, E.; Echavarren, A. M. J. Org. Chem. 1991, 56, 3497.
16. (a) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1988, 110, 4051.
17. (b) Kubo, A.; Nakahara, S. Heterocycles 1988, 27, 2095.
18. (c) Nakahara, S.; Tanaka, Y.; Kubo, A.; Heterocycles 1996, 43, 2113.
19. Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478
20. Úbeda, J. I.; Villacampa, M.; Avendaño, C. Synthesis 1998, 1176.
21. Walsh, A. Synthesis 1980, 677.
22. Fehnel, E. A. J. Org. Chem. 1966, 31, 2899.
23. Tapia, R. A.; Quintanar, C.; Valderrama, J. A. Heterocycles 1996, 43, 447.
24. The isolation of these adducts is not frequent, see for instance: Bouaziz, Z.; Nebois, P.; Fillion, H. Tetrahedron 1995, 51, 6573.
25. Villacampa, M.; Pérez, J. M.; Avendaño, C.; Menéndez, J. C. Tetrahedron 1994, 50, 10047.