Abstract
5-(Arylmethylidene)pyrimidine-2,4,6(1H,3H,5H)-triones reacted with substituted benzaldehyde oximes in the presence of N-bromosuccinimide and triethylamine to give 1,4-diaryl-2-oxa-3,7,9-triazaspiro-[4.5]dec-3-ene-6,8,10-triones and 3,4-diaryl-1,2,5-oxadiazole N-oxides.
Similar content being viewed by others
References
Baranski, A. and Kelarev, V.I., Chem. Heterocycl. Compd., 1990, vol. 26, p. 371. doi https://doi.org/10.1007/BF00497204
Baranski, A. and Shvekhgeimer, G.A., Pol. J. Chem., 1982, vol. 56, p. 459.
Ladyzhnikova, T.D., Altukhov, K.V., and Solov’ev, N.A., Zh. Org. Khim., 1986, vol. 22, p. 2618.
Tyrkov, A.G. and Suikhanova, B.G., Russ. J. Org. Chem., 1999, vol. 35, p. 1299.
Tyrkov, A.G., Russ. J. Org. Chem., 2002, vol. 38, p. 1218. doi https://doi.org/10.1023/A:1020934400960
Grundmann, C. and Richter, R., J. Org. Chem., 1968, vol. 33, p. 476. doi https://doi.org/10.1021/jo01265a120
Yurtaeva, E.A. and Tyrkov, A.G., Russ. J. Org. Chem., 2016, vol. 52, p. 289. doi https://doi.org/10.1134/s1070428016020214
Shvekhgeimer, G.A., Baranski, A., and Grzegozek, M., Synthesis, 1976, no. 9, p. 611. doi https://doi.org/10.1055/s-1976-24140
Granik, V.G., Osnovy meditsinskoi khimii (Fundamentals of Medicinal Chemistry), Moscow: Vuzovskaya Kniga, 2001, p. 248.
Mashkovskii, M.D., Lekarstvennye sredstva (Medicines), Moscow: Novaya Volna, 2002, 14th ed., vol. 1, p. 432.
Kirchner, J.G., Thin-Layer Chromatography, Perry, E.S., Ed., New York: Wiley, 1978, 2nd ed. Translated under the title Tonkosloinaya khromatografiya, Moscow: Mir, 1981, vol. 1, pp. 129, 228.
Luzhnova, S.A., Tyrkov, A.G., Gabitova, N.M., and Yurtaeva, E.A., Pharm. Chem. J., 2018, vol. 52, p. 506. doi https://doi.org/10.1007/s11094-018-1849-7
Weygand, C., Organisch-chemische Experimentierkunst, Leipzig, Johann Ambrosius Barth, 1938. Translated under the title Metody eksperimenta v organicheskoi khimii, Moscow: Inostrannaya Literatura, 1952, vol. 2, p. 288.
Reaktsii i metody issledovaniya organicheskikh compoundi (Reactions and Methods of Investigation of Organic Compounds), Moscow: GNTIKhL, 1957, vol. 6, p. 39.
Khmel’nitskii, L.I., Novikov, S.S., and Godovikova, T.I., Khimiya furoksanov (stroenie i sintez) (Chemistry of Furoxans. Structure and Synthesis), Moscow: Nauka, 1981, p. 129.
Funding
This study was performed under financial support by the Ministry of Science and Higher Education of the Russian Federation (project no. 4.9288.2017BCh).
Author information
Authors and Affiliations
Corresponding authors
Additional information
Conflict of Interests
The authors declare the absence of conflict of interests.
Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 7, pp. 1079–1083.
Rights and permissions
About this article
Cite this article
Tyrkov, A.G., Yurtaeva, E.A. Heterocyclization of 5-(Arylmethylidene)pyrimidine-2,4,6(1H,3H,5H)-triones with Arenecarbaldehyde Oximes in the Presence of N-Bromosuccinimide and Triethylamine. Russ J Org Chem 55, 978–982 (2019). https://doi.org/10.1134/S1070428019070108
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428019070108