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Heterocyclization of 5-(Arylmethylidene)pyrimidine-2,4,6(1H,3H,5H)-triones with Arenecarbaldehyde Oximes in the Presence of N-Bromosuccinimide and Triethylamine

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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.

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References

  1. Baranski, A. and Kelarev, V.I., Chem. Heterocycl. Compd., 1990, vol. 26, p. 371. doi https://doi.org/10.1007/BF00497204

    Article  Google Scholar 

  2. Baranski, A. and Shvekhgeimer, G.A., Pol. J. Chem., 1982, vol. 56, p. 459.

    CAS  Google Scholar 

  3. Ladyzhnikova, T.D., Altukhov, K.V., and Solov’ev, N.A., Zh. Org. Khim., 1986, vol. 22, p. 2618.

    CAS  Google Scholar 

  4. Tyrkov, A.G. and Suikhanova, B.G., Russ. J. Org. Chem., 1999, vol. 35, p. 1299.

    CAS  Google Scholar 

  5. Tyrkov, A.G., Russ. J. Org. Chem., 2002, vol. 38, p. 1218. doi https://doi.org/10.1023/A:1020934400960

    Article  CAS  Google Scholar 

  6. Grundmann, C. and Richter, R., J. Org. Chem., 1968, vol. 33, p. 476. doi https://doi.org/10.1021/jo01265a120

    Article  CAS  Google Scholar 

  7. Yurtaeva, E.A. and Tyrkov, A.G., Russ. J. Org. Chem., 2016, vol. 52, p. 289. doi https://doi.org/10.1134/s1070428016020214

    Article  CAS  Google Scholar 

  8. Shvekhgeimer, G.A., Baranski, A., and Grzegozek, M., Synthesis, 1976, no. 9, p. 611. doi https://doi.org/10.1055/s-1976-24140

  9. Granik, V.G., Osnovy meditsinskoi khimii (Fundamentals of Medicinal Chemistry), Moscow: Vuzovskaya Kniga, 2001, p. 248.

    Google Scholar 

  10. Mashkovskii, M.D., Lekarstvennye sredstva (Medicines), Moscow: Novaya Volna, 2002, 14th ed., vol. 1, p. 432.

    Google Scholar 

  11. 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.

  12. 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

    Article  CAS  Google Scholar 

  13. 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.

    Google Scholar 

  14. Reaktsii i metody issledovaniya organicheskikh compoundi (Reactions and Methods of Investigation of Organic Compounds), Moscow: GNTIKhL, 1957, vol. 6, p. 39.

  15. 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.

    Google Scholar 

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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).

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Correspondence to A. G. Tyrkov or E. A. Yurtaeva.

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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.

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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

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  • DOI: https://doi.org/10.1134/S1070428019070108

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