The reductive dehalogenation of halosubstituted naphthazarins and quinizarins as a simple route to parent compounds

Synthetic Communications

Volumn 28, Issue 12, 1998, Pages 2149-2157

  Anufriev, Victor Ph ^a   Malinovskaya, Galina V ^a   Novikov, Vyacheslav L ^a   Balanyova, Nadezhda N ^a   Polonik, Sergey G ^a  

^a PACIFIC INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

NAPHTHAZARIN; QUINIZARIN;

ARTICLE; CHEMICAL REACTION; DEHALOGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; REDUCTION;

EID: 0031865993     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808007029     Document Type: Article

References (29)

1. (a) Thomson, R. H. "Naturally Occurring Quinones", London, N. Y.: Butterworths, 1957, 1st ed.
2. (b) Academic Press, 1971, 2nd ed.
3. (c) London, N. Y.: Chapman & Hall, 1987, 3rd ed.
4. (a) Tanaka, H.; Yoshioka, T.; Shimauchi, Y.; Yoshimoto, A.; Ishikura, T. Tetrahedron Lett. 1984, 25, 3351-3354.
5. (b) Burns, C. J.; Gill, M.; Saubern, S. Aust. J. Chem. 1991, 44, 1427-1445.
6. (c) Terada, A.; Tanoue, Y.; Hatada, A.; Sakamoto, H. Bull. Chem. Soc. Jpn. 1987, 60, 205-213.
7. (d) Novikov, V. L.; Balanyova, N. N.; Moiseenkov, A. M.; Elyakov, G. B. Bull. Russ. Acad. Sciences, Div. Chem. Science. 1992, 41, 1485-1495.
8. (a) Burns, C. J.; Gill, M. Aust. J. Chem. 1991, 44, 1447-1458.
9. (b) Larsen, D. S.; Stoodley, R. T. Tetrahedron. 1990, 46, 4711-4732.
10. (a) Brown, E. G.; Cambie, R. C.; Holroyd, S. E.; Johnson, M.; Rutledge, P. S.; Woodgate, P. D. Tetrahedron Lett. 1989, 30, 4735-4736.
11. (b) Bennani, F.; Florent, J.-C.; Koch, M.; Monneret, C. Tetrahedron Lett. 1984, 25, 3975-3978.
12. (c) Argade, A. B.; Mehendale, A. R.; Ayyangar, N. R. Tetrahedron Lett. 1986, 27, 3529-3532.
13. (d) Van Dufat-Trihn, H.; Seguin, E.; Tillequin, F.; Monneret, C.; Koch, M. Chem. Pharm. Bull. 1989, 37, 3294-3300.
14. (e) Deguin, B.; Florent, J.-C.; Monneret, C. J. Org. Chem. 1991, 56, 405-411.
15. (f) Cousson, A.; Le Gouadec, G.; Monneret, C.; Florent, J.-C. J. Chem. Soc. Chem. Commun. 1993, 388-390.
16. West Germany Patent N3244452. 1983. CA 1983, 99, 58731.
17. Ulrich, H.; Richter R. "Die para-Chinone der Benzol-und Naphthalin-Reihe", in Houben I.; Weyl T. "Methoden der Organischen Chemie", Stuttgart: Georg Thieme Verlag, 1977, Bd. 7/3a.
18. Singh, I.; Moore, R. E.; Chang, C.W.J.; Ogata, R.T.; Scheuer, P.J. Tetrahedron. 1968, 24, 2969-2978.
19. Huot, R.; Brassard, P. Canad. J. Chem. 1974, 54, 838-842.
20. (a) Waldmann, H.; Ulsperger E. Chem. Ber. 1950, 83, 178-181.
21. (b) Horowska, B.; Mazerska, Z.; Ledochowski, A.; Cristalli, G.; Franchetti, P.; Martelli, S. Eur. J. Med. Chem. 1988, 23, 91-96.
22. (a) Bruce D.B.; Thomson, R.H. J. Chem. Soc. 1955, 1089-1096.
23. (b) Lewis, J. R.; Paul, J. Z. Naturforsch. 1977, 32B, 1473-1475.
24. Rodriguez, J.-G.; De Pablo, A.; Smith-Verdier, P.; Florencio, F.; Garcia-Blanco, S. Bull. Chem. Soc. Jpn. 1986, 59, 3957-3961.
25. Anufriev, V. Ph.; Novikov, V. L.; Malinovskaya, G. V.; Glazunov, V. P. Synth. Commun. 1997, 27, 119-126.
26. A compound 3j was synthesized from 3e in a manner analogous to that described by Polonik, S. G.; Tolkach A. M.; Uvarova N. I. Zh. Org. Khim. 1994, 30, 248-253 (In Russian).
27. Moore, R.E.; Singh, I.; Scheuer, P.J. J. Org. Chem. 1966, 31, 3645-3650.
28. "Dictionary of Organic Compounds", Ex. Ed. Buckingham J., N. Y., London, Toronto: Chapman & Hall, 1982, 5th ed., Vol. 2, P. 1907.
29. In case of substrate 1m, pyridine was removed under vacuum and the solid was treated with 2N HCl (30 ml).