A new method for the synthesis of 2-hydroxy-3-nitro-1,4-naphthoquinones: Application to regiospecific preparation of unsymmetrical nitrobiquinones

Journal of Organic Chemistry

Volumn 71, Issue 17, 2006, Pages 6648-6651

  Yu, Min ^a   Malinakova, Helena C ^b   Stagliano, Kenneth W ^a  

^a Illinois Institute of Technology   (United States)

^b UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HIGH YIELD; HYDROXYQUINONE; NAPHTHOQUINONES; NITRONIUM TETRAFLUOROBORATE;

CHLORINE; NEGATIVE IONS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

HYDROCARBONS;

1,4 NAPHTHOQUINONE DERIVATIVE; 2 CHLORO 3 NITRO 1,2 NAPHTHOQUINONE DERIVATIVE; 2 HYDROXY 3 NITRO 1,4 NAPHTHOQUINONE DERIVATIVE; 3 NITRO 2,2' BINAPHTHOQUINONE DERIVATIVE; BORIC ACID; CHLORINE; NITROBIQUINONE DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; QUANTUM YIELD; STEREOSPECIFICITY; SUBSTITUTION REACTION;

HYDROXYLATION; MOLECULAR STRUCTURE; NAPHTHOQUINONES; NITROGEN; STEREOISOMERISM;

EID: 33747380554     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060825c     Document Type: Article

References (24)

1. Decosterd, L. A.; Parsons, I. C.; Gustafson, K. R.; Cardellina, J. H., II; McMahon, J. B.; Gragg, G. M.; Murata, Y.; Pannell, L. K.; Steiner, J. R.; Boyd, M. R. J. Am. Chem. Soc. 1993, 115, 6673-6679.
2. Thomson, R. H. Naturally Occurring Quinones IV. Recent Advances; Chapman & Hall: London, Great Britain, 1997.
3. Laatsch, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 423-424.
4. Okamoto, I.; Dio, H.; Kotani, E.; Takeya, T. Tetrahedron Lett. 2001, 42, 2987-2989.
5. Ogata, T.; Okamoto, I.; Dio, H.; Kotani, E.; Takeya, T. Tetrahedron Lett. 2003, 44, 2041-2044.
6. Liebeskind, L. S.; Yu, M. S.; Yu, R. H.; Wang, J.; Hagen, K. S. J. Am. Chem. Soc. 1993, 115, 9048-9055.
7. Liebeskind, L. S.; Riesinger, S. W. Tetrahedron Lett. 1991, 32, 5681-5682.
8. Bringmann, G.; Gotz, R.; Keller, P. A.; Walter, R.; Boyd, M. R.; Lang, F.; Garcia, A.; Walsh, J. J.; Tellitu, I.; Bhaskar, K. V.; Kelly, T. R. J. Org. Chem. 1988, 63, 1090-1097.
9. Davies, M. W.; Johnson, C. N.; Harrity, J. P. A. J. Org. Chem. 2001, 66, 3525-3532.
10. Yin, J.; Liebeskind, L. S. J. Org. Chem. 1998, 63, 5726-5727.
11. Jiang, M. X.; Rawat, M.; Wulff, W. D. J. Am. Chem. Soc. 2004, 126, 5970-5971.
12. Smith, L. I.; Austin, F. L. J. Am. Chem. Soc. 1942, 64, 528-533.
13. Finley, K. T. The Chemistry of the Functional Groups. The Chemistry of the Quinonoid Compounds; John Wiley & Sons: New York, 1974; Vol. 2, pp 1047-1072.
14. Emadi, A.; Harwood, J. S.; Kohanim, S.; Stagliano, K. W. Org. Lett. 2002, 4, 521-525.
15. Stagliano, K. W.; Emadi, A.; Lu, Z.; Malinakova, H. C.; Twenter, B.; Yu, M.; Holland, L. E.; Rom, A. M.; Harwood, J. S.; Amin, R.; Johnson, A. A.; Pommier, Y. Bioorg. Med. Chem. Lett. 2006, 14, 5651-5665.
16. Buckle, D. R.; Cantello, B. C. C.; Smith, H.; Smith, R. J.; Spicer, B. A. J. Med. Chem. 1977, 20, 1059-1064.
17. Kuhn, S. J.; Olah, G. A. J. Am. Chem. Soc. 1958, 80, 6541-6545.
18. Kuhn, S. J.; Olah, G. A. J. Am. Chem. Soc. 1961, 83, 4564-4571.
19. -1 corresponding to the symmetrical stretch of the N-O bond.
20. -1, symmetrical stretch of the N-O bond) in the IR spectrum confirmed the presence of a nitro group in nitrobiquinone 8.
21. Cannon, J. R.; Josshi, K. R.; McDonald, I. A.; Retallack, R. W.; Sierakowski, A. F.; Wong, L. C. H. Tetrahedron Lett. 1975, 32, 2795-2798.
22. Jacobsen, E. N.; Vander Velde, S. L. J. Org. Chem. 1995, 60, 5380-5381.
23. Kasturi, T. R.; Arunachalam, T. Can. J. Chem. 1966, 44, 1086-1089.
24. 1H NMR spectra due to significant broadening.