Preparation of substituted hydroquinones and benzofurans from 1,4-quinone monoketals

Synthesis

Volumn , Issue 20, 2006, Pages 3419-3424

  Salom Roig, Xavier J ^a   Renaud, Philippe ^b  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b UNIVERSITY OF BERN   (Switzerland)

Author keywords

Heterocycles; Organometallic reagents; Phenols; Quinones; Rearrangements

Indexed keywords

AROMATIC COMPOUNDS; AROMATIZATION; CATALYSIS; ORGANOMETALLICS; PHENOLS; REACTION KINETICS; SUBSTITUTION REACTIONS;

BENZOFURANS; HETEROCYCLES; HYDROQUINONES; ORGANOMAGNESIUM COMPOUNDS; QUINONES; REARRANGEMENTS;

KETONES;

1,4 QUINONE; 5 METHOXYBENZOFURAN; BENZOFURAN DERIVATIVE; HYDROQUINONE DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MEDICAL RESEARCH;

EID: 33750586735     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950236     Document Type: Article

References (27)

1. (a) Patil, A. D.; Freyer, A. J.; Killmer, L.; Offen, P.; Carte, B.; Jurewicz, A. J.; Johnson, R. K. Tetrahedron 1997, 53, 5047.
2. (b) Hallock, Y. F.; Cardellina, J. H.; Boyd, M. R. Nat. Prod. Lett. 1998, 11, 153.
3. 1,2-Addition to quinone monoketal has been reported: (a) Swenton, J. S.; Bradin, D.; Gates, B. D. J. Org. Chem. 1991, 56, 6156.
4. (b) McKillop, A.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. J. Chem. Soc., Chem. Commun. 1992, 1589.
5. (c) Trân-Huu-Dâu, M. E.; Wartchow, R.; Winterfeldt, E.; Wong, Y. S. Chem. Eur. J. 2001, 7, 2349. The same products are also available by anodic oxidation of 4-substituted aromatic ethers.
6. For review articles, see: (d) Swenton, J. S. Acc. Chem. Res. 1983, 16, 74.
7. (e) Swenton, J. S. In The Chemistry of Quinonoid Compounds, Vol. 2, Part 2; Patai, S.; Rappoport, Z., Eds.; John Wiley: New York, 1988, 899.
8. (a) Stern, A. J.; Swenton, J. S. J. Org. Chem. 1988, 53, 2465.
9. (b) Stern, A. J.; Rohde, J. J.; Swenton, J. S. J. Org. Chem. 1989, 54, 4413.
10. (c) Swenton, J. S.; Callinan, A.; Wang, S. J. Org. Chem. 1992, 57, 78.
11. (d) Swenton, J. S.; Carpenter, K.; Chen, Y.; Kerns, M. L.; Morrow, G. W. J. Org. Chem. 1993, 58, 3308.
12. (e) Swenton, J. S.; Callinan, A.; Chen, Y.; Rohde, J. J.; Kerns, M. L.; Morrow, G. W. J. Org. Chem. 1996, 61, 1267.
13. (f) Carreño, M. C.; Pérez Gonzalez, M.; Fischer, J. Tetrahedron Lett. 1995, 36, 4893.
14. (g) Marks, T. M.; Morrow, G. W. Tetrahedron Lett. 1992, 33, 2269.
15. (h) Evans, D. A.; Cain, P. A.; Wong, R. Y. J. Am. Chem. Soc. 1977, 99, 7083.
16. (i) Parker, K. A.; Coburn, C. A. J. Am. Chem. Soc. 1991, 113, 8516.
17. (j) Parker, K. A.; Su, D. S. J. Org. Chem. 1996, 61, 2191.
18. The dienone-phenol rearrangement of p-quinols has been described before: (a) Guildford, A. J.; Turner, R. W. Synthesis 1982, 46.
19. (b) Ward, R. S.; Pelter, A.; Abd-El-Ghani, A. Tetrahedron 1996, 52, 1303.
20. (c) Ward, R. S.; Pelter, A.; Abd-El-Ghani, A. J. Chem. Soc., Perkin Trans. 1 1992, 2249.
21. (d) Pelter, A.; Ward, R. S.; Abd-El-Ghani, A. J. Chem. Soc., Perkin Trans. 1 1996, 1353.
22. To the best of our knowledge, only two examples concerning 1,2-migrations in p-quinol ketals have been reported. Alkenyl shift: (e) Parker, K. A.; Coburn, C. A.; Koh, Y. J. Org. Chem. 1995, 60, 2938.
23. Phenyl shift: (f) Morrow, G. W.; Marks, T. M.; Sear, D. L. Tetrahedron 1995, 51, 10115.
24. See reference 2c for the preparation of 1.
25. Kinugasa, M.; Harada, T.; Oku, A. J. Org. Chem. 1996, 61, 6772.
26. For a review on the preparation of benzofurans, see: Dell, C. P. Fused Five-Membered Hetarenes with One Heteroatom, In Science of Synthesis, Vol. 10; Thomas, J., Ed.; Georg Thieme Verlag: Stuttgart, 2000, 11.
27. Pelter, A.; Elgendy, S. M. A. J. Chem. Soc., Perkin Trans. 1 1993, 1891.