Abstract
1,4-Nucleophilic addition reactions of 3-nitrothiochromone with indoles gave a number of novel trans-2-(indol-3-yl)-3-nitrothiochroman-4-ones in 36–89% yields. During the reactions, the thiopyrone ring underwent no opening.
References
R. J. Sundberg, The Chemistry of Indoles, Academic Press, New York, 1996, 113 pp.
Y. Sugita, I. Yokoe, Heterocycles, 1996, 43, 2503.
V. Ya. Sosnovskikh, R. A. Irgashev, Tetrahedron Lett., 2007, 48, 7436.
V. Ya. Sosnovskikh, R. A. Irgashev, A. A. Levchenko, Tetrahedron, 2008, 64, 6607.
V. Ya. Sosnovskikh, R. A. Irgashev, Russ. Chem. Bull. (Int. Ed.), 2006, 55, 2294 [Izv. Akad. Nauk, Ser. Khim., 2006, 2208].
V. Ya. Sosnovskikh, R. A. Irgashev, Lett. Org. Chem., 2007, 4, 344.
G. J. P. Becket, G. P. Ellis, M. I. U. Trindade, J. Chem. Res. (S), 1978, 47.
D. T. Connor, P. A. Young, M. von Strandtmann, J. Heterocycl. Chem., 1981, 18, 697.
M. Tanaka, Y. Murakami, H. Morita, K. Takagi, Chem. Pharm. Bull., 1985, 33, 2129.
K. Takagi, M. Tanaka, Y. Murakami, K. Ogura, K. Ishii, H. Morita, T. Aotsuka, J. Heterocycl. Chem., 1987, 24, 1003.
G. Haas, J. L. Stanton, T. Winkler, J. Heterocycl. Chem., 1981, 18, 619.
J. F. Geissler, J. L. Roesel, T. Meyer, U. P. Trinks, P. Traxler, N. B. Lydon, Cancer Res., 1992, 52, 4492.
D. V. Sevenard, M. Vorobyev, V. Ya. Sosnovskikh, H. Wessel, O. Kazakova, V. Vogel, N. E. Shevchenko, V. G. Nenajdenko, E. Lork, G.-V. Röschenthaler, Tetrahedron, 2009, 65, 7538.
V. Ya. Sosnovskikh, D. V. Sevenard, V. S. Moshkin, V. O. Iaroshenko, P. Langer, Tetrahedron, 2010, 66, 7322.
D. V. Sevenard, M. A. Barabanov, V. Ya. Sosnovskikh, Russ. Chem. Bull. (Int. Ed.), 2010, 59, 297 [Izv. Akad. Nauk, Ser. Khim., 2010, 289].
G. Sabitha, Aldrichim. Acta, 1996, 29, 15.
C. K. Ghosh, S. K. Karak, J. Heterocycl. Chem., 2005, 42, 1035.
V. Ya. Sosnovskikh, V. S. Moshkin, Khim. Geterotsikl. Soedin., 2012, 144 [Chem. Heterocycl. Compd. (Engl. Transl.), 2012, 48, 139].
V. O. Iaroshenko, S. Mkrtchyan, A. Gevorgyan, M. Vilches-Herrera, D. V. Sevenard, A. Villinger, T. V. Chochikyan, A. Saghiyan, V. Ya. Sosnovskikh, P. Langer, Tetrahedron, 2012, 68, 2532.
D. Ostrovskyi, V. O. Iaroshenko, A. Petrosyan, S. Dudkin, I. Ali, A. Villinger, A. Tolmachev, P. Langer, Synlett, 2010, 2299.
V. Yu. Korotaev, V. Ya. Sosnovskikh, I. B. Kutyashin, M. I. Kodess, Russ. Chem. Bull. (Int. Ed.), 2006, 55, 317 [Izv. Akad. Nauk, Ser. Khim., 2006, 309].
P. R. Giles, C. M. Marson, Aust. J. Chem., 1992, 45, 439.
G. I. Junghietu, V. A. Budylin, A. N. Kost, Preparativnaya khimiya indola [The Preparative Chemistry of Indole], Chisinau, 1975, p. 263 (in Russian).
Organic Syntheses, V. 20, John Wiley and Sons, New York, 1940, 117 pp.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2166–2168, November, 2012.
Rights and permissions
About this article
Cite this article
Barabanov, M.A., Sevenard, D.V. & Sosnovskikh, V.Y. Synthesis of trans-2-(indol-3-yl)-3-nitrothiochroman-4-ones from 3-nitrothiochromone and indoles. Russ Chem Bull 61, 2183–2185 (2012). https://doi.org/10.1007/s11172-012-0308-y
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-012-0308-y