Abstract
The 7,7′-dideoxy analog of islandoquinone, binaphthazarin of a new structural type, bearing a 2-oxo-2,3-dihydro-1,4-naphthoquinone moiety was synthesized. The carbonyl group at the C(2) atom of this binaphthazarin easily adds water to give the correspondinggem-diol. Comparison of the spectral characteristics of the prepared diol and islandoquinone made it possible to elucidate more precisely the structure of the latter.
Similar content being viewed by others
References
A. Ya. Chizhova, V. F. Anufriev, and V. L. Novikov,Zh. Org. Khim., 1995,30, 237 [Russ. J. Org. Chem., 1995,21 (Engl. Transl.)].
L. S. Stepanenko, O. E. Krivoshchekova, P. S. Dmitrenok, and O. B. Maximov,Phytochemistry, 1997,46, 565.
S. C. Hooker,J. Am. Chem. Soc., 1936,58, 1168.
M. J. Ettlinger,J. Am. Chem. Soc., 1950,72, 3472.
A. Ya. Chizhova, Ph.D. (Chem.) Thesis, Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the RAS, Vladivostok, 1996 (in Russian).
R. E. Moore and P. J. Scheuer,J. Org. Chem., 1966,31, 3272.
R. H. Thomson, inNaturally Occurring Quinones, 2nd ed., Academic Press, London-New York, 1971, 266.
W. Bachmann and W. Struve, inOrganic Reactions, Ed. R. Adams, Wiley, New York, 1942.
F. Huber and M. Schmeisser, inHandbuch der Praparativen Anorganischen Chemie, Ed. G. Brauer, Ferdinand Enke Verlag, Stuttgart, 1975.
L. F. Fieser and M. Fieser,Reagents for Organic Synthesis, J. Wiley and Sons, New York-London, 1968.
Author information
Authors and Affiliations
Additional information
For Part 2, see Ref. 1.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 947–952, May, 1999.
Rights and permissions
About this article
Cite this article
Chizhova, A.Y., Kochergina, T.Y., Anufriev, V.F. et al. The chemistry of naphthazarin derivatives. Russ Chem Bull 48, 938–943 (1999). https://doi.org/10.1007/BF02494641
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF02494641