One-pot synthesis of isoquinoline-5,8-dione derivatives from acylquinones and enamines

Author:

Kobayashi Kazuhiro,Takanohashi Atsushi,Watanabe Shinya,Morikawa Osamu,Konishi Hisatoshi

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference11 articles.

1. Thomson, R. H. In Naturally Occurring Quinones III–Recent Advances; Chapman Hall: London, 1987; pp. 633–666; McKee, T. C.; Ireland, C. M. J. Nat. Prod. 1987, 50, 754–756; Kubo, A.; Kitahara, Y.; Nakahara, S. Chem. Pharm. Bull. 1989, 37, 1384–1386; He, H.; Faulkner, J. D. J. Org. Chem., 1989, 54, 5822–5824; Baker, R. A.; Tatum, J. H.; Namec, S. Jr. Mycopathologia 1990, 111, 9–15; Phelps, D. C.; Nemec, S.; Baker, R.; Mansell, R. Phytopathology 1990, 80, 298–302; Parisot, D.; Devys, M.; Barbier, M. Phytochemistry 1990, 29, 3364–3365; Davidson, B. S. Tetrahedron Lett. 1992, 33, 3721–3724; Edrada, R. A.; Proksch, P.; Wray, V.; Christ, R.; Witte, L.; Van Soest, R. W. M. J. Nat. Prod. 1996, 59, 973–976. See also, Berquist, P. R.; Wells, R. J. In Marine Natural Products; Scheuer, P. J., Ed.; Academic Press: New York, 1983; Vol. 5, pp. 6–8 and 197–198; Arai, T.; Kubo, A. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1983; Vol. 21, pp. 55–100.

2. Ma, C. Y.; Ho, C.; Walton, B. T.; Kao, G. L.; Guerin, M. R. Environ. Sci. Technol. 1984, 18, 362–364; Konoshima, T.; Kozuka, M.; Koyama, J.; Okatani, T.; Tagahara, K.; Tokuda, H. J. Nat. Prod. 1989, 52, 987–995; Krapcho, A. P.; Petry, M. E.; Getahun, Z.; Landi, J. J. Jr.; Polsenberg, J. F.; Gallagher, C. E.; Maresch, M. J.; Hacker, M. P.; Giuliani, F. C.; Beggiolin, G.; Pezzoni, G.; Menta, E.; Manzotti, C.; Oliva, A.; Spinelli, S.; Tognella, S. J. Med. Chem. 1994, 37, 828–837.

3. For recent reports: (a) Ohgaki, E.; Motoyoshiya, J.; Narita, S.; Kakurai, T.; Hayashi, S.; Hirakawa, K. J. Chem. Soc., Perkin Trans. 1 1990, 3109–3112; (b) Xiong, Y.; Moore, H. W. J. Org. Chem. 1997, 61, 9168–9177; (c) Werner, W.; Grefe, U.; Ihn, W.; Tresselt, D.; Winter, S.; Paulus, E. Tetrahedron 1997, 53, 109–118; (d) Molina, P.; Vidal, A.; Tovar, F. Synthesis 1997, 963–966; (e) Krapcho, A. P.; Waterhouse, D. J. Heterocycles 1999, 51, 7737–7750; (f) Kesteleyn, B.; De Kimpe, N. J. Org. Chem. 2000, 65, 640–644. For biosynthesis of natural isoquinolinequinone derivatives: (g) Parisot, D.; Devy, M.; Barbier, M. J. Antibiot. 1989, 42, 1189–1190.

4. Synthesis of 1-amino- and 1-hydroxy-9,10-anthraquinone derivatives based on reaction sequences between 2-acetyl-1,4-naphthoquinone and enamines

5. Read, G.; Ruiz, V. M. J. Chem. Soc., Perkin Trans. 1 1973, 235–243.

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