A synthesis of 1-azaanthraquinones via Diels-Alder reaction of 4- hydroxy- and 4-methoxy-2-phenylquinolinequinones with 3-trimethylsilyloxy- 1,3-butadienes: Observation of inverse regioselectivity

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 9, 1998, Pages 1356-1363

  Horiguchi, Yoshie ^a   Toeda, Akio ^a   Tomoda, Katuhiro ^a   Suzuki, Hideki ^a   Sano, Takehiro ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

1 azaanthraquinone; 1 methoxy 3 trimethylsilyloxybutadiene; Diels Alder reaction; Quinolinequinone; Regioselectivity

Indexed keywords

1 AZAANTHRAQUINONE DERIVATIVE; 1,3 BUTADIENE DERIVATIVE; 3 TRIMETHYLSILYLOXY 1,3 BUTADIENE; 4 HYDROXY 2 PHENYLQUINOLINEQUINONE; 4 METHOXY 2 PHENYLQUINOLINEQUINONE; ANTHRAQUINONE DERIVATIVE; HYDROXYL GROUP; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DRUG SYNTHESIS; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; STEREOCHEMISTRY;

EID: 0031682590     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.1356     Document Type: Article

References (15)

1. Johnson R. K., Zee-Cheng R. K., Acton E. M., Henry D. W., Cheng C. C., Cancer Treat. Rep., 63, 425-439 (1979).
2. Munshi J. F., Joullie M. M., J. Heterocycl. Chem., 4, 133-136 (1967); Ogaki E., Motoyoshi J., Narita S., Kakurai T., Hayashi S., Hirakawa K., J. Chem. Soc., Perkin Trans. 1, 1990, 3109-3112.
3. Munshi J. F., Joullie M. M., J. Heterocycl. Chem., 4, 133-136 (1967); Ogaki E., Motoyoshi J., Narita S., Kakurai T., Hayashi S., Hirakawa K., J. Chem. Soc., Perkin Trans. 1, 1990, 3109-3112.
4. Potts K. T., Bhattacharjee D., Walsh E. B., J. Org. Chem., 51, 2011-2021 (1986).
5. Kelly T. R., Montury M., Tetrahedron Lett., 1978, 4309-4310; idem, ibid., 1978, 4311-4314; Trost B. M., Vladuchick W. C., Bridges A. J., J. Am. Chem. Soc., 102, 3554-3572 (1980).
6. Kelly T. R., Montury M., Tetrahedron Lett., 1978, 4309-4310; idem, ibid., 1978, 4311-4314; Trost B. M., Vladuchick W. C., Bridges A. J., J. Am. Chem. Soc., 102, 3554-3572 (1980).
7. Kelly T. R., Montury M., Tetrahedron Lett., 1978, 4309-4310; idem, ibid., 1978, 4311-4314; Trost B. M., Vladuchick W. C., Bridges A. J., J. Am. Chem. Soc., 102, 3554-3572 (1980).
8. Inhoffen H. H., Muxfeldt H., Schaefer H., Kramer H., Croat. Chem. Acta, 29, 329-345 (1957); Muxfeldt H., Angew. Chem., 74, 825-828 (1962); Kelly T. R., Gillard J. W., Goerner R. N., Jr., Lyding J. M., J. Am. Chem. Soc., 99, 5513-5514 (1977); Kelly T. R., Montury M., Tetrahedron Lett., 1978, 4311-4314.
9. Inhoffen H. H., Muxfeldt H., Schaefer H., Kramer H., Croat. Chem. Acta, 29, 329-345 (1957); Muxfeldt H., Angew. Chem., 74, 825-828 (1962); Kelly T. R., Gillard J. W., Goerner R. N., Jr., Lyding J. M., J. Am. Chem. Soc., 99, 5513-5514 (1977); Kelly T. R., Montury M., Tetrahedron Lett., 1978, 4311-4314.
10. Inhoffen H. H., Muxfeldt H., Schaefer H., Kramer H., Croat. Chem. Acta, 29, 329-345 (1957); Muxfeldt H., Angew. Chem., 74, 825-828 (1962); Kelly T. R., Gillard J. W., Goerner R. N., Jr., Lyding J. M., J. Am. Chem. Soc., 99, 5513-5514 (1977); Kelly T. R., Montury M., Tetrahedron Lett., 1978, 4311-4314.
11. Inhoffen H. H., Muxfeldt H., Schaefer H., Kramer H., Croat. Chem. Acta, 29, 329-345 (1957); Muxfeldt H., Angew. Chem., 74, 825-828 (1962); Kelly T. R., Gillard J. W., Goerner R. N., Jr., Lyding J. M., J. Am. Chem. Soc., 99, 5513-5514 (1977); Kelly T. R., Montury M., Tetrahedron Lett., 1978, 4311-4314.
12. Toda J., Fuse T., Kishikawa E., Ando N., Negishi R., Horiguchi Y., Sano T., Heterocycles, 38, 2091-2097 (1994).
13. Chan T.-H., Brownbridge P., J. Am. Chem. Soc., 102, 3534-3538 (1980).
14. The formation of the hydroquinone may he explained by an oxidation-reduction reaction between the quinone 10a and the Diels-Alder adduct 22.
15. The product 26a was not acetylated because of the extreme insolubility in pyridine.