A practical synthesis of pyrene-4,5-dione

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 9995-9996

  Young, Erick R R ^a   Funk, Raymond L ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON; PYRENE 4,5 DIONE; PYRENE DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032567522     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970344g     Document Type: Article

References (25)

1. (a) Dansett, P.; Jerina, D. M. J. Am. Chem. Soc. 1974, 96, 1224.
2. (b) Jeyaraman, R.; Murray, R. W. J. Am. Chem. Soc. 1984, 106, 2462.
3. Morquardt, H.; Kuroki, T.; Huberman, E.; Selkirk, J. K; Heidelberger, C.; Grover, P. L.; Sims, P. Cancer Res. 1972, 32, 716.
4. Shou, M.; Yang, S. K. Drug Metab. Dispos. 1988, 16, 173.
5. (e) Hetlich, R. H.; Thornton-Manning, J. R.; Kinouchi, T.; Kataoka, K.; Ohnishi, Y. Mutât. Res. 1991, 262, 232.
6. Harvey, R. G. In Polycyclic Aroma tic Hydrocarbons: Chemistry and Carcinogenicity; Cambridge University Press: New York, 1991.
7. With ort/io-phenylenediamine: (a) Oberender, F. G.; Dixon, J. A. J. Org. Chem. 1959, 24, 1226.
8. With trimethyl phosphite: (b) Ramirez, F.; Bhatia, S. B.; Patwardhan, A. V.; Chen, E. H.; Smith, C. P. J. Org. Chem. 1968, 33, 20.
9. With sulfamide: Ege, G.; Beisiegel, E. Synthesis 1974, 22. With alkenes:
10. Tintel, C.; Terheijden, J.; Lughtenburg, J.; Cornelisse, J. Tetrahedron Lett. 1987, 28, 2060.
11. With 1,3-diarylpropanones: (e) Pascal, R. A., Jr.; McMillan, W. D.; Van Engen, D.; Eason, R. G. J. Am. Chem. Soc. 1987, 109, 4660.
12. (a) Dewar, M. J. S. J. Am. Chem. Soc. 1952, 74, 3357.
13. (b) Cook, J. W.; Schoental, R. J. Am. Chem. Soc. 1950, 72, 47.
14. Cho, H.; Harvey, R. G. J. Chem. Soc., Perkin Trans. 1 1976, 836.
15. Fatiadi, A. J. Synthesis 1974, 4, 257.
16. (e) Ranganathan, S.; Ranganathan, D.; Ramachandran, P. V. Tetrahedron 1984, 40, 3145.
17. (a) Goh, S. H.; Harvey, R. G. J. Am. Chem. Soc. 1973, 95, 242.
18. (b) Moriarity, R. M.; Dansette, P.; Jerina, P. M. Tetrahedron Lett. 1975, 30 2557
19. (a) Harvey, R. G.; Rabideau, P. W. Tetrahedron Lett. 1970, 12, 3695.
20. (b) Cho, H.; Harvey, R. G. Tetrahedron Lett. 1974, 16, 1491.
21. Funk, R. L.; Young, E. R. R.; Williams, R. M.; Flanagan, M. F.; Cecil, T. L. J. Am. Chem. Soc. 1996, 118, 3291.
22. For the preparation of a phenanthrenequinone using this approach, see: Wittig, G.; Zimmerman, H. Chem. Ber. 1953, 86, 629.
23. Salto, Y.; Arale, S.; Sugita, Y.; Kurato, N. (Nippon Shokubai Kagaku Kogyo Co. Ltd.) Eur. Pat. Appl. EP 103, 368.
24. Bocchi, V.; Casnati, G.; Dossena, A.; Marchell, R. Synthesis 1979, 961.
25. Finley, T. K Chem. Rev. 1964, 64, 573.