Ring opening SN2′ reactions of 1,4,5,8-diepoxy-1,4,5,8-tetrahydroanthracenes by organoltihium reagents

Heterocycles

Volumn 47, Issue 2, 1998, Pages 977-984

  Arjona, Odón ^a   León, Marisa ^a   Plumet, Joaquín ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009548888     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-s(n)23     Document Type: Article

References (18)

1. See, for instance: H. Hart, N. Raju, M. A. Meador, and D. L. Ward, J. Org. Chem., 1983, 48, 4357;
2. H. Hart, Ch. Lai, G. Ch. Nwokogu, and S. Shamouilian, Tetrahedron, 1987, 43, 5203;
3. P. R. Ashton, G. R. Brown, N. S. Isaacs, D. Giuffrida, F. H. Kohnke, J. P. Mathias, A. M. Z. Slawin, D. R. Smith, J. F. Stoddart, and D. J. Williams, J. Am. Chem. Soc., 1992, 114, 6330;
4. P. R. Ashton, J. P. Mathias, and J. F. Stoddart, Synthesis, 1993, 221.
5. F. Raymo, F. H. Kohnke, F. Cardullo, U. Girreser, and J. F. Stoddart, Tetrahedron, 1992, 48, 6827.
6. For general accounts on the ring opening of oxabicyclic systems including the use of organolithium reagents, see: M. Lautens, Synlett, 1993, 3, 177;
7. S. Woo and B. A. Keay, Synlett, 1996, 135.
8. For some recent references on the synthetic utility of these reactions, see: J. L. Aceña, O. Arjona, F. Iradier, and J. Plumet, Tetrahedron Lett., 1996, 37, 105;
9. J. L. Aceña, E. de Alba, O. Arjona, and J. Plumet, Tetrahedron Lett., 1996, 37, 3043.
10. For some selected references see: R. Caple, G. M. S. Chen, and J. D. Nelson, J. Org. Chem., 1971, 36, 2874;
11. A. M. Jeffrey, H. C. J.Yeh, D. M. Jerina, R. M. De Marinis, Ch. H. Foster, D. E. Piccolo, and G. A. Berchtold, J. Am. Chem. Joc., 1974, 96, 6929;
12. H. C. Brown and J. V. N. Vara Prasad, J. Org. Chem., 1985, 50, 3002;
13. L. G. French, E. E., Fenlon, and T. P. Charlton, Tetrahedron Lett., 1991, 52, 851.
14. Substituted polycyclic aromatic hydrocarbons are compounds of current interest since they have frequently shown to possess biological activity different from the parent hydrocarbons. See S. S. Hecht, A. A. Melikian, and S. Amim, in "Polycyclic Aromatic Hydrocarbon Carcinogenesis: Structure-Activity Relationship"; ed. by S. K. Yang and B. D. Silverman, Boca Ratón, Florida, 1988, Vol. 1, p. 95.
15. On the other hand compounds related to the anthracene ring system are important agent for the treatment of psoriosis. For recent papers related to the synthesis of these kind of compounds, see: H. Prinz, W. Wiegrebe, and K. Muller, J. Org. Chem., 1996, 61, 2853;
16. H. Prinz, T. Burgeweister, W. Wiegrebe, and K. Muller, J. Org. Chem., 1996, 61, 2857;
17. H. Prinz, W. Wiegrebe, and K. Muller, J. Org. Chem., 1996, 61, 2861.
18. This nucleophilic ring opening would be reminiscent with the other bridge opening of epoxyarene systems, related with the carcinogenic activity of these compounds, see: R. Gopalaswamy and M. Koreeda, Tetrahedron Lett., 1996, 37, 3651 and references therein.