Regioselective synthesis of 1,5-diazaanthraquinones via Diels-Alder reaction of 4-hydroxy-quinolinequinone with 1-aza-1,3-butadiene

Heterocycles

Volumn 53, Issue 2, 2000, Pages 315-322

  Horiguchi, Yoshie ^a   Toeda, Akio ^a   Tomoda, Katsuhiro ^a   Sano, Takehiro ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; ANTHRAQUINONE DERIVATIVE; HETEROCYCLIC COMPOUND; METHYL GROUP; QUINOLINOL DERIVATIVE;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGEN BOND; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034141228     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-8765     Document Type: Article

References (15)

1. T. Ozturk, "The Alkaloids", Vol. 49, ed. by G. A. Cordell, Academic Press Inc., San Diego, 1997, pp. 79-219.
2. K. T. Potts, E. B. Walsh, and D. Bhattacharjee, J. Org. Chem., 1987, 52, 2285; C. Gesto , E. de la Cuesta, and C. Avendano, Tetrahedron, 1989, 45, 4477: C. Gesto, E. de la Cuesta, C. Avendano, and F. Emling, J. Pham. Sci., 1992, 81, 815; B. Ocana, M. Espada, and C. Avendano, Tetrahedron, 1994, 50, 10047; R. A. Tapia, C. Quintanar, and A. Valderrama, Heterocycles, 1996, 43, 447; J. M. Pérez, P. L. Alvarado, M. Á. Alonso, C. Avendano, and J. C. Ménendez, Tetrahedron Lett, 1996, 37, 6955.
3. K. T. Potts, E. B. Walsh, and D. Bhattacharjee, J. Org. Chem., 1987, 52, 2285; C. Gesto , E. de la Cuesta, and C. Avendano, Tetrahedron, 1989, 45, 4477: C. Gesto, E. de la Cuesta, C. Avendano, and F. Emling, J. Pham. Sci., 1992, 81, 815; B. Ocana, M. Espada, and C. Avendano, Tetrahedron, 1994, 50, 10047; R. A. Tapia, C. Quintanar, and A. Valderrama, Heterocycles, 1996, 43, 447; J. M. Pérez, P. L. Alvarado, M. Á. Alonso, C. Avendano, and J. C. Ménendez, Tetrahedron Lett, 1996, 37, 6955.
4. K. T. Potts, E. B. Walsh, and D. Bhattacharjee, J. Org. Chem., 1987, 52, 2285; C. Gesto , E. de la Cuesta, and C. Avendano, Tetrahedron, 1989, 45, 4477: C. Gesto, E. de la Cuesta, C. Avendano, and F. Emling, J. Pham. Sci., 1992, 81, 815; B. Ocana, M. Espada, and C. Avendano, Tetrahedron, 1994, 50, 10047; R. A. Tapia, C. Quintanar, and A. Valderrama, Heterocycles, 1996, 43, 447; J. M. Pérez, P. L. Alvarado, M. Á. Alonso, C. Avendano, and J. C. Ménendez, Tetrahedron Lett, 1996, 37, 6955.
5. K. T. Potts, E. B. Walsh, and D. Bhattacharjee, J. Org. Chem., 1987, 52, 2285; C. Gesto , E. de la Cuesta, and C. Avendano, Tetrahedron, 1989, 45, 4477: C. Gesto, E. de la Cuesta, C. Avendano, and F. Emling, J. Pham. Sci., 1992, 81, 815; B. Ocana, M. Espada, and C. Avendano, Tetrahedron, 1994, 50, 10047; R. A. Tapia, C. Quintanar, and A. Valderrama, Heterocycles, 1996, 43, 447; J. M. Pérez, P. L. Alvarado, M. Á. Alonso, C. Avendano, and J. C. Ménendez, Tetrahedron Lett, 1996, 37, 6955.
6. K. T. Potts, E. B. Walsh, and D. Bhattacharjee, J. Org. Chem., 1987, 52, 2285; C. Gesto , E. de la Cuesta, and C. Avendano, Tetrahedron, 1989, 45, 4477: C. Gesto, E. de la Cuesta, C. Avendano, and F. Emling, J. Pham. Sci., 1992, 81, 815; B. Ocana, M. Espada, and C. Avendano, Tetrahedron, 1994, 50, 10047; R. A. Tapia, C. Quintanar, and A. Valderrama, Heterocycles, 1996, 43, 447; J. M. Pérez, P. L. Alvarado, M. Á. Alonso, C. Avendano, and J. C. Ménendez, Tetrahedron Lett, 1996, 37, 6955.
7. K. T. Potts, E. B. Walsh, and D. Bhattacharjee, J. Org. Chem., 1987, 52, 2285; C. Gesto , E. de la Cuesta, and C. Avendano, Tetrahedron, 1989, 45, 4477: C. Gesto, E. de la Cuesta, C. Avendano, and F. Emling, J. Pham. Sci., 1992, 81, 815; B. Ocana, M. Espada, and C. Avendano, Tetrahedron, 1994, 50, 10047; R. A. Tapia, C. Quintanar, and A. Valderrama, Heterocycles, 1996, 43, 447; J. M. Pérez, P. L. Alvarado, M. Á. Alonso, C. Avendano, and J. C. Ménendez, Tetrahedron Lett, 1996, 37, 6955.
8. Y. Kitahara, F. Tamura, and A. Kubo, Chem. Pharm. Bull., 1994, 42, 1363; Y. Kitahara, F. Tamura, M. Nishimura, and A. Kubo, Tetrahedron, 1998, 54, 8421.
9. Y. Kitahara, F. Tamura, and A. Kubo, Chem. Pharm. Bull., 1994, 42, 1363; Y. Kitahara, F. Tamura, M. Nishimura, and A. Kubo, Tetrahedron, 1998, 54, 8421.
10. J. M. Pérez, P. L. Alvarado, C. Avendano, and J. C. Ménendez, Tetrahedron Lett., 1998, 39, 673.
11. Y. Horiguchi, A. Toeda, K. Tomoda, H. Suzuki, and T. Sano, Chem. Pharm. Bull., 1998, 46, 1356.
12. Y. Horiguchi, K. Tomoda, and T. Sano, Heterocycles, 1999, 51, 1669.
13. A. J. Birch, D. N. Butler, and J. B. Siddal, J. Chem. Soc., 1964, 2941; K. T. Potts, D. Bhattacharjee, and E. B. Walsh, J. Org. Chem., 1986, 51, 2011.
14. A. J. Birch, D. N. Butler, and J. B. Siddal, J. Chem. Soc., 1964, 2941; K. T. Potts, D. Bhattacharjee, and E. B. Walsh, J. Org. Chem., 1986, 51, 2011.
15. A. Waldner, Helv. Chim. Acta, 1988, 71, 486.