Abstract
The Diels-Alder reaction of new 1-(3,4-dimethoxyphenyl)- or 1-(2,4-dimethoxyphenyl)-2-R-3-trimethylsiloxy-1,3-butadienes with 2,5- and 2,6-dibromo-, and 2-bromo-6-methyl-1,4-benzoquinones regioselectively yields substituted 7-hydroxy-5-(dimethoxyphenyl)-1,4-naphthoquinones. By cycloaddition of the siloxydienes to naphthoquinone, bromonaphthoquinone, and juglone the corresponding substituted 3-hydroxy-1-(dimethoxyphenyl)-9,10-anthraquinones or their 4,4a-dihydro or 1,1a,4,4a-tetrahydro derivatives were obtained.
Similar content being viewed by others
REFERENCES
Abegaz, B.M., Bezabih, M., Msuta, T., Brun, R., Menche, D., Muhlbacher, J., and Bringmann, G., J. Nat. Prod., 2002, vol. 65, p. 1117.
Nechepurenko, I.V., Shul'ts, E.E., and Tolstikov, G.A., Russ. J. Org. Chem., 2001, vol. 37, p. 1276.
Il'ina, T.V., Semenova, E.A., Pronyaeva, T.R., Pokrovskii, A.G., Nechepurenko, I.V., Shul'ts, E.E., Andreeva, O.A., Kochetkov, S.N., and Tolstikov, G.A., Dokl. Ross. Akad. Nauk, 2002, vol. 382, p. 829.
Organikum. Organisch-chemisches Grundpraktikum, Berlin: Wissenschaften, 1976, 15th edn. Translated under the title Organikum, Moscow: Mir, 1979, vol. 2, p. 138.
Beilsteins Handbuch der organischen Chemie, H, vol. 8, p. 291; ibid., EV, vol. 8, p. 627; ibid., ZV, vol. 8, p. 326.
Adeva, M., Sahagun, H., Caballero, E., Clairac, R., Medarde, M., and Tome, F., J. Org. Chem., 2000, vol. 65, p. 3387.
Boisvert, L. and Brassard, P., J. Org. Chem., 1988, vol. 53, p. 4052; Roberge, G. and Brassard, P., J. Org. Chem., 1981, vol. 46, p. 4161.
Gordon, A.J. and Ford, R.A., The Chemist's Companion, New York: Wiley, 1972. Translated under the title Sputnik khimika, Moscow: Mir, 1976, p. 296.
Kalinowsky, H., Berger, S., and Brawn, S., 13-C NMR Spektroskopie, New York: Georg Thieme, 1984, p. 475.
Tolstikov, G.A., Shul'ts, E.E., Safarova, G.M., Spirikhin, L.V., and Panasenko, A.A., Zh. Org. Khim., 1990, vol. 26, p. 1283.
Shul'ts, E.E., Petrova, T.N., Rybalova, T.V., Gatilov, Yu.V., and Tolstikov, G.A., Russ. J. Org. Chem., 1998, vol. 34, p. 845.
Hofle, G., Tetrahedron, 1977, vol. 33, p. 1963; Bowden, B.F., Cameron, D.W., Crossley, M.J., Feutrill, G.I., Griffiths, P.G., and Kelly, D.P., Aust. J. Chem., 1979, vol. 32, p. 769.
Organic Syntheses, Noland, W.E., Ed., New York: Wiley, 1963, collect. vol. 4. Translated under the title Sintezy organicheskikh preparatov, Moscow: Inostrannaya Literatura, 1953, vol. 4, p. 340; Jeffreys, J.A., J. Chem. Soc., 1959, vol. 6, p. 2153.
Lyons, J.M. and Thomson, R.H., J. Chem. Soc., 1953, no. 10, p. 2910.
Organic Syntheses, Noland, W.E., Ed., New York: Wiley, 1963, collect. vol. 4. Translated under the title Sintezy organicheskikh preparatov, Moscow: Inostrannaya Literatura, 1953, vol. 4, p. 578.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Nechepurenko, I.V., Shul'ts, E.E. & Tolstikov, G.A. Synthesis of 5-Aryl-1,4-naphthoquinone and 1-Aryl-9,10-anthraquinone Derivatives by Cycloaddition of 1-(Dimethoxyphenyl)-3-trimethylsiloxy-1,3-butadienes to 1,4-Benzoquinones and 1,4-Naphthoquinones. Russian Journal of Organic Chemistry 39, 1436–1450 (2003). https://doi.org/10.1023/B:RUJO.0000010560.88282.d3
Issue Date:
DOI: https://doi.org/10.1023/B:RUJO.0000010560.88282.d3