Abstract
N-(Carbamoyl)-1-aryl-2,3,4,5,6,7-hexahydro-3-hydroxy-6,6-dimethyl-2,4-dioxo-1H-indole-3-carboxamides upon dissolution in DMSO or DMF undergo a reversible isomerization to 5-(2-arylamino-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-5-hydroxypyrimidine-2,4,6(1H,3H,5H)-triones.
Similar content being viewed by others
References
W. Cocker, J. T. Edward, T. F. Holley, D. M. S. Wheeler, Chemistry and Industry (London), 1955, 1484.
V. A. Khrustalev, K. N. Zelenin, V. V. Alekseev, J. Org. Chem. USSR (Engl. Transl.), 1981, 17, 2451 [Zh. Org. Khim., 1981, 17, 2451].
K. N. Zelenin, V. A. Alekseev, V. A. Khrustalev, S. I. Yakimovich, V. N. Nikolaev, N. V. Koshmina, J. Org. Chem. USSR (Engl. Transl.), 1984, 20, 180 [Zh. Org. Khim., 1984, 20, 180].
K. N. Zelenin, M. Yu. Malov, I. P. Bezhan, V. A. Khrustalev, S. I. Yakimovich, Chem. Heterocycl. Compd. (Engl. Transl.), 1985, 835 [Khim. Geterotsikl. Soedin., 1985, 1000].
K. N. Zelenin, A. Yu. Ershov, M. Yu. Malov, S. I. Yakimovich, Dokl. Akad. Nauk SSSR, 1986, 289, 1132 [Dokl. Chem. (Engl. Transl.), 1986].
K. N. Zelenin, V. V. Alekseev, Chem. Heterocycl. Compd. (Engl. Transl.), 1992, 708 [Khim. Geterotsikl. Soedin., 1992, 851].
K N. Zelenin, V. V. Alekseyev, O. B. Kuznetsova, V. N. Torocheshnikov, L. A. Khorseeva, Tetrahedron, 1993, 49, 5327.
K. N. Zelenin, V. V. Alekseyev, P. B. Terentiev, O. B. Kuznetsova, V. V. Lashin, V. V. Ovcharenko, V. V. Torocheshnikov, L. A. Khorseyeva, A. A. Sorokin, Mendeleev Commun., 1993, 4, 168.
A. Yu. Ershov, A. V. Gribanov, V. A. Gindin, A. I. Kol´tsov, Zh. Org. Khim., 1995, 31, 1054 [Russ. J. Org. Chem. (Engl. Transl.), 1995, 31].
A. Yu. Ershov, A. V. Dobrodumov, Chem. Heterocycl. Compd. (Engl. Transl.), 2000, 36, 708 [Khim. Geterotsikl. Soedin., 2000, 36, 825].
Z. Shan, B. Wan, G. Wang, Helv. Chim. Acta, 2002, 85, 1062.
A. Yu. Ershov, Chem. Heterocycl. Compd. (Engl. Transl.), 2002, 38, 730 [Khim. Geterotsikl. Soedin., 2002, 38, 828].
C. Maiereanu, M. Darabantu, G. Ple, Y. Ramondenc, C. Berghian, Rev. Roumaine Chim., 2005, 50 (1), 29.
V. Yu. Korotaev, A. Yu. Barkov, P. A. Slepukhin, M. I. Kodess, V. Ya. Sosnovskikh, Tetrahedron Lett., 2011, 52, 5764.
V. V. Alekseyev, S. I. Yakimovich, I. V. Zerova, M. B. Egorova, J. Sinkkonen, Chem. Heterocycl. Compd. (Engl. Transl.), 2013, 49, 1490 [Khim. Geterotsikl. Soedin., 2013, 49, 1606].
L. Yu. Xue, B. Jiang, M.-S. Tu, Sh. J. Tu, Tetrahedron Lett., 2012, 53, 6611.
L. Yu. Ukhin, K. Yu. Suponitsky, E. N. Shepelenko, L. V. Belousova, O. S. Popova, G. S. Borodkin, Mendeleev Commun., 2015, 25, 135.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Academician of the Russian Academy of Sciences V. I. Minkin on the occasion of his 80th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0664—0667, March, 2015.
Rights and permissions
About this article
Cite this article
Borodkin, G.S., Zaichenko, S.B., Borodkina, I.G. et al. Ring-ring isomerization in the series of N-(carbamoyl)-1-aryl-2,3,4,5,6,7-hexahydro-3-hydroxy-6,6-dimethyl-2,4-dioxo-1H-indole-3-carboxamides. Russ Chem Bull 64, 664–667 (2015). https://doi.org/10.1007/s11172-015-0915-5
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-015-0915-5