Derivatives of anthra[2,3-b]furan-5,10-diones hold promise for various fields of science and technology, especially in the search for biologically active compounds. This review covers all currently known methods for the cyclization of linear anthrafurandiones, the first examples of which were synthesized approximately 30 years ago. The material has been arranged mainly in the order of increasing degree of substitution in anthrafurandiones. All the literature methods for functional group transformations providing access to a range of anthrafurandiones unavailable by direct heterocyclization have been considered separately.
Similar content being viewed by others
References
V. Ya. Fain, 9,10-Anthraquinones and their Applications, [in Russian], Khimiya, Мoscow: Center for Photochemistry, Russian Academy of Sciences (1999), p. 92.
V. A. Barachevsky, in: J. C. Crano, R. J. Guglielmetti (edotors), Organic Photochromic and Thermochromic Compounds, Plenum Press, New York, London (1999), p. 267.
B. G. Katzung, Basic and Clinical Pharmacology, Ch. 55, Cancer Chemotherapy, 10th ed., McGraw-Hill Medical Publishing Division, New York (2006), p. 905.
A. E. Shchekotikhin, V. A. Glazunova, L. G. Dezhenkova, E. K. Shevtsova, V. F. Traven’, J. Balzarini, H. S. Huang, A. A. Shtil, and M. N. Preobrazhenskaya, Eur. J. Med. Chem., 46, 423 (2011).
A. E. Shchekotikhin, V. A. Glazunova, Y. N. Luzikov, V. N. Buyanov, O. Y. Susova, A. A. Shtil, and M. N. Preobrazhenskaya, Bioorg. Med. Chem., 14, 5241 (2006).
A. E. Shchekotikhin, V. A. Glazunova, L. G. Dezhenkova, Y. N. Luzikov, Y. B. Sinkevich, L. V. Kovalenko, V. N. Buyanov, J. Balzarini, F. C. Huang, J. J. Lin, H. S. Huang, A. A. Shtil, and M. N. Preobrazhenskaya, Bioorg. Med. Chem., 17, 1861 (2009).
А. E. Shchekotikhin, Е. K. Shevtsova, and V. F. Traven, Zh. Org. Khim., 43, 1687 (2007). [Russ. J. Org. Chem., 43, 1686 (2007).]
А. E. Shchekotikhin, Е. K. Shevtsova, Yu. N. Luzikov, V. A. Barachevsky, and V. F. Traven, Zh. Org. Khim., 44, 864 (2008). [Russ. J. Org. Chem., 44, 855 (2007).]
J. G. Curd, R. L. Capizzi, and J. F. W. Keana, WO Pat. Appl. 2006031719.
M. V. Gorelik, Chemistry of Anthraquinones and their Derivatives, [in Russian], Moscow, Khimiya (1983), pp. 241-243.
G. B. Liu, H. Mori, and S. Katsumura, Chem. Commun., 2251 (1996).
M. Watanabe, W.-T. Su, Y. J. Chang, T.-H. Chao, Y.-S. Wen, and T. J. Chow, Chem. Asian J., 8, 60 (2013).
А. А. Moroz, T. P. Galevskaya, and M. S. Shvartsberg, Zh. Vses. Khim. Obsch. im. Mendeleeva, 32, 711 (1987).
L. Mavoungou-Gomesm and J. Cabares, C. R. Seances Acad. des Sci., Ser. C, 287 (3), 73 (1978).
L. Mavoungou-Gomes and J. Cabares, Bull. Soc. Chim. Fr., 3, 401 (1986).
G. J. O'Malley and M. P. Cava, Tetrahedron Lett., 26, 6159 (1985).
J. Mann, H. J. Holland, and T. Lewis, Tetrahedron, 43, 2533 (1987).
M. Al Hariri, F. Pautet, and H. Fillion, Synlett, 6, 459 (1994).
M. Al Harin, F. Pautet, H. Fillion, M. Domard, and B. Fenet, Tetrahedron, 51, 9595 (1995).
M. V. Gorelik and E. V. Mishina, Zh. Org. Khim., 19, 2185 (1983).
M. V. Gorelik and E. V. Mishina, USSR Inventor's Certificate 973577; Chem. Abstr., 98, 108875 (1983).
A. E. Shchekotikhin, Yu. N. Luzikov, V. N. Buyanov, and M. N. Preobrazhenskaya, Khim. Geterotsikl. Soedin., 191 (2009). [Chem. Heterocycl. Compd., 45, 151 (2009).]
A. S. Tikhomirov, A. E. Shchekotikhin, Yu. N. Luzikov, A. M. Korolev, and M. N. Preobrazhenskaya, Khim. Geterotsikl. Soedin., 264 (2013). [Chem. Heterocycl. Compd., 49, 241 (2013).]
A. S. Tikhomirov, A. E. Shchekotikhin, Yu. N. Luzikov, A. M. Korolev, and M. N. Preobrazhenskaya, Khim. Geterotsikl. Soedin., 1464 (2011). [Chem. Heterocycl. Compd., 47, 1206 (2012).]
D. Mal, S. Ray, and I. Sharma, J. Org. Chem., 72, 4981 (2007).
O. Khoumeri, M. D. Crozet, T. Terme, and P. Vanelle, Tetrahedron Lett., 50, 6372 (2009).
C. A. Townsend, S. G. Davis, M. Koreeda, and B. Hulin, J. Org. Chem., 50, 5428 (1985).
C. A. Townsend, Y. Isomura, S. G. Davis, and J. A. Hodge, Tetrahedron, 45, 2263 (1989).
P. Allevi, M. Anastasia, P. Ciuffreda, A. Fiecchi, and A. Scala, J. Org. Chem., 52, 5469 (1987).
S. Cogoi, A. E. Shchekotikhin, A. Membrino, Y. B. Sinkevich, and L. E. Xodo, J. Med. Chem., 56, 2764 (2013).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 193-208, February, 2014.
Rights and permissions
About this article
Cite this article
Tikhomirov, A.S., Shchekotikhin, A.E. & Preobrazhenskaya, M.N. Methods for the Synthesis and Modification of Linear Anthrafurandiones (Review). Chem Heterocycl Comp 50, 171–184 (2014). https://doi.org/10.1007/s10593-014-1459-6
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-014-1459-6