Abstract
7-Arylpyrano[4,3-d]pyrimidinium salts were synthesized starting from 1,3,6-trimethyluracil. In the reactions with N-nucleophiles, these salts were found to undergo recyclization of the pyrylium ring, whereas the addition of C- and O-nucleophiles occurs at free position 5 of the system.
Similar content being viewed by others
References
V. V. Kostrub, E. B. Tsupak, A. F. Smol’yakov, Izv. Akad. Nauk, Ser. Khim., 2009, 1426 [Russ. Chem. Bull., Int. Ed., 2009, 58, 1469].
E. B. Tsupak, M. A. Shevchenko, V. V. Kostrub, Yu. N. Tkachenko, Izv. Akad. Nauk, Ser. Khim., 2007, 2251 [Russ. Chem. Bull., Int. Ed., 2007, 56, 2330].
V. V. Kostrub, E. B. Tsupak, Yu. N. Tkachenko, M. A. Shevchenko, Izv. Akad. Nauk, Ser. Khim., 2008, 1720 [Russ. Chem. Bull., Int. Ed., 2008, 57, 1754].
V. V. Kostrub, E. B. Tsupak, Y. V. Nelyubina, Mendeleev Commun., 2009, 19, 220.
V. V. Kostrub, E. B. Tsupak, Izv. Akad. Nauk, Ser. Khim., 2009, 1422 [Russ. Chem. Bull., Int. Ed., 2009, 58, 1465].
E. B. Tsupak, I. A. Gavrilenko, V. V. Kostrub, Mendeleev Commun., 2009, 19, 157.
K. Hirota, T. Asao, I. Sugiyama, S. Senda, Heterocycles, 1981, 15, 289.
A. I. Rakhimov, I. E. Kryukov, Zh. Org. Khim., 2000, 792 [Russ. J. Org. Chem. (Engl. Transl.), 2000, 36, 763].
G. N. Dorofeenko, E. I. Sadekova, V. M. Goncharova, Khim. Geterotsikl. Soedin., 1970, 1308 [Chem. Heterocycl. Compd. (Engl. Transl.), 1970, 6, 1218].
J. Körösi, T. Láng, Chem. Ber., 1974, 107, 3883.
S. V. Tolkunov, S. Yu. Suikov, M. Yu. Zubritskii, V. I. Dulenko, Khim. Geterotsikl. Soedin., 1998, 1137 [Chem. Heterocycl. Compd. (Engl. Transl.), 1998, 8, 1137].
V. V. Kostrub, Ph. D. (Chem.) Thesis, Southern Federal University, Rostov-on-Don, 2009, 126 pp. (in Russian).
E. V. Kuznetsov, I. V. Shcherbakova, A. T. Balaban, Adv. Heterocycl. Chem., 1990, 50, 157.
A. T. Balaban, A. Dinculescu, G. N. Dorofeenko, G. W. Fischer, A. V. Koblic, V. V. Mezheritskii, W. Schroth, Adv. Heterocycl. Chem., Suppl. 2, Academic Press, New York, USA, 1982, 434 pp.
Z.-L. Hu, W.-J. Qian, Z.-J. Yao, S. Wang, S. Wang, Org. Lett., 2009, 11, 4676.
R. Aveta, G. Doddi, N. Insam, F. Stegel, J. Org. Chem., 1980, 45, 5160.
S. Senda, K. Hirota, K. Banno, J. Med. Chem., 1972, 15, 471.
A. J. Gordon, R. A. Ford, Chemist’s Companion: A Handbook of Practical Data, Techniques, and References, Wiley, New York, 1973, 560 pp.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 620—627, March, 2012.
Rights and permissions
About this article
Cite this article
Gavrilenko, I.A., Kostrub, V.V. & Tsupak, E.B. Pyrano[4,3-d]pyrimidinium salts 5. Synthesis of 7-aryl-1,3-dimethyl-2,4-dioxo-1H,3H-pyrano[4,3-d]pyrimidinium salts and their reactions with nucleophiles. Russ Chem Bull 61, 623–630 (2012). https://doi.org/10.1007/s11172-012-0090-x
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-012-0090-x