A general procedure for the efficient synthesis of (alkylamino)naphthoquinones

Journal of Organic Chemistry

Volumn 61, Issue 9, 1996, Pages 3031-3033

  Couladouros, Elias A ^a   Plyta, Zoi F ^a   Papageorgiou, Vassilios P ^a  

^a AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

14 NAPHTHOQUINONE DERIVATIVE; NAPHTHAZACIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029945336     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9517252     Document Type: Article

References (37)

1. (a) Lin, T-S.; Xu, S-P.; Zhu, L-Y.; Cosby, L.; Sartonelli, A. J. Med. Chem. 1989, 32, 1467.
2. (b) Stefanska, B.; Dzieduszycka, M.; Martelli, S.; Antonini, I.; Borowski, E. J. Org. Chem. 1993, 58, 1568.
3. (c) Konoshima, T.; Kozuka, M.; Koyama, J.; Okatani, T.; Tagahara, K.; Tokuda, H. J. Nat. Prod. 1989, 52(5), 987.
4. Lin, T.-S.; Xu, S.-P.; Zhu, L.-Y.; Divo, A.; Sartonelli, A. J. Med. Chem. 1991, 34, 1634.
5. (a) Takagi, K.; Matsuoka, M.; Hamano, K.; Kitao, T. Dyes Pigments 1984, 5, 241.
6. (b) Matsuoka, M.; Takagi, K.; Obayashi, H.; Wakasugi, K; Kitao, T. J. Soc. Dyers Colour. 1983, 99, 257.
7. (a) Kikuchi, M.; Komatsu, K.; Nakano, M. Dyes Pigments 1990, 12(2), 107.
8. (b) Yoshida, M. Jpn Kokai Tokkyo Koho 1987, JP 86-94307, 860423 (Chem. Abstr. 1988 108, 173357y).
9. (c) Kikushi, M.; Nakano, M. Sen'i Gakkaishi 1987, 43(11), 602.
10. (a) Escolastico, C.; Santa Maria, M. D.; Claramunt, R. M.; Jimeno, M. L.; Alkorta, I.; Foces-Foces, C.; Cano, F. H.; Elguero, J. Tetrahedron 1994, 50, 12489.
11. (b) Catalan, J.; Febero, F.; Guijarro, M. S.; Claramunt, R. M.; Santa Maria, M. D.; Foces-Foces, M.; Cano, F. H.; Elguero, J.; Sastre, R. J. Am. Chem. Soc. 1990, 112, 747.
12. Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873 and references therein.
13. Furusaki, A.; Watanabe, T. Chem. Pharm. Bull. 1973, 21, 931 and references therein.
14. Lancini, G.; Zanichelli, W. Antibiotics; Perlman, D., Ed.; Academic Press: New York, 1977; pp 531-600.
15. Lanz, T.; Tropf, S.; Marner, F-J.; Schroder, J.; Schroder, G. J. Biol. Chem. 1991, 266, 9971.
16. (a) Parker, K.; Sworin, M. J. Org. Chem. 1981, 46, 3218.
17. (b) Kita, Y.; Tohma, H.; Inagaki, M.; Hatanaka, K.; Yakura, T. J. Am. Chem. Soc. 1992, 114, 2175.
18. (c) Aristoff, P.; Johnson, P. J. Org. Chem. 1992, 57, 6234.
19. (a) Matsuoka, M.; Takei, T.; Kitao, T. Chem. Lett. 1979, 627 and references therein.
20. (b) Castillo, G.; Ellames, G. J.; Osborne, A. G.; Sammes, P. G. J. Chem. Res. Miniprint 1978, 836.
21. (c) For a recent review on the nucleophilic reactions of quinones see Kutyrev, A. Tetrahedron 1991, 47, 8043.
22. (a) Matsuoka, M.; Hamano, K.; Kitao, T. Synthesis 1984, 953.
23. (b) Nakazumi, H.; Kondo, K.; Kitao, T. Synthesis 1982, 878.
24. (c) See also ref 13.
25. Falling, S.; Rapoport, H. J. Org. Chem. 1980, 45, 1260.
26. (a) Barton D. H. R.; Chern, C.-Y.; Tachdjian, C. Heterocycles 1994, 37, 793.
27. See also (b) Fourrey, J. L.; Beauclaire, J.; Wei Yuan, C. J. Chem. Soc., Perkin Trans. 1 1987, 1841.
28. For the preparation of 2-halonaphthazarines see: (a) Zahn, K.; Ochwat, P. Ann. 1928, 462, 72.
29. (b) Grinev, A. N.; Terente'ev, A. P. Vestnik Moskov. Univ., Ser. Mat., Mekh., Astron., Fiz., Khim. 1957, 12(6), 147 (Chem. Abstr. 53, 3187f).
30. (b) Grinev, A. N.; Terente'ev, A. P. Vestnik Moskov. Univ., Ser. Mat., Mekh., Astron., Fiz., Khim. 1957, 12(6), 147 (Chem. Abstr. 53, 3187f).
31. For the preparation of 2-bromonaphthoquinone, 2-bromojuglone, and 2-bromo-5-acetyljuglone see: Grunwell J.; Karipides, A.; Wigal, C.; Heinzman, S.; Parlow, J.; Surso, J.; Clayton, L.; Fleitz, F.; Daffner, M.; Stevens, J. J. Org. Chem. 1991, 56, 91.
32. For the preparation of 3-bromojuglone and 2-bromo-5-methyljuglone see: Hannan, R. L.; Barber, R. B.; Rapoport, H. J. Org. Chem. 1979, 13, 2153.
33. 13C NMR spectra, see: Heinzman, S. W.; Grunwell, J. R. Tetrahedron Lett. 1980, 21, 4305.
34. Pearson, M.; Jensky, B.; Greer, F.; Hangstrom, J.; Wells, N. J. Org. Chem. 1978, 43, 4617.
35. The reaction time of the oxidation dependent upon the substitution of the aromatic ring.
36. Both regioisomers of aminojuglone derivatives were independently prepared according to the literature (ref 11b) and found to be identical with those prepared following our method.
37. The yield of compound 2g seems to depend strongly on the time of air-oxidation and workup manipulations. Extension of the oxidation period beyond 10 min dramatically decreases the yield.