Abstract
8-Aroyl-3,4-dihydropyrrolo[2,1-c][1,4]oxazine-1,6,7(1H)-triones reacted with 1,3-diphenylguanidine to give 9-aroyl-6-(2-hydroxyalkyl)-2-iminio-4,7-dioxo-1,3-diphenyl-1,3,6-triazaspiro[4.4]non-8-en-8-olates. Spectral characteristics of the synthesized compounds were fairly similar to those of 9-benzoyl-6(2-hydroxyphenyl)-2-iminio-4,7-dioxo-1,3-diphenyl-1,3,6-triazaspiro[4.4]non-8-en-8-olate whose structure was determined by X-ray analysis. Spiro derivatives of hydantoin are promising from the viewpoint of studies in the field of pharmaceutical chemistry and medicine.
Similar content being viewed by others
REFERENCES
Konnert, L., Lamaty, F., Martinez, J., and Colacino, E., Chem. Rev., 2017, vol. 117, p. 13757. https://doi.org/10.1021/acs.chemrev.7b00067
Cho, S.H., Kim, S.H., and Shin, D., Eur. J. Med. Chem., 2019, vol. 164, p. 517. https://doi.org/10.1016/j.ejmech.2018.12.066
Mashevskaya, I.V., Kol’tsova, S.V., Voronina, E.V., Odegova, T.F., and Maslivets, A.N., Pharm. Chem. J., 2001, vol. 35, p. 18. https://doi.org/10.1023/A:1010494525001
Babenysheva, A.V., Maslivets, V.A., and Maslivets, A.N., Russ. J. Org. Chem., 2007, vol. 43, p. 1577. https://doi.org/10.1134/S107042800710034X
Kobelev, A.I., Tretyakov, N.A., Stepanova, E.E., Dmitriev, M.V., Rubin, M., and Maslivets, A.N., Beilstein J. Org. Chem., 2019, vol. 15, p. 2864. https://doi.org/10.3762/bjoc.15.280
Tretyakov, N.A. and Maslivets, A.N., Russ. J. Org. Chem., 2020, vol. 56, p. 726. https://doi.org/10.1134/S1070428020040260
Tutynina, N.M., Tairova, L.F., and Maslivets, A.N., Russ. J. Org. Chem., 2014, vol. 50, p. 1218. https://doi.org/10.1134/s1070428014080284
Kobelev, A.I., Dmitriev, M.V., and Maslivets, A.N., Russ. J. Org. Chem., 2021, vol. 57, p. 108. https://doi.org/10.1134/S1070428021010152
Tretyakov, N.A., Dmitriev, M.V., and Maslivets, A.N., Russ. J. Org. Chem., 2020, vol. 56, p. 1367. https://doi.org/10.1134/S1070428021010152
CrysAlisPro, AgilentTechnologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET).
Palatinus, L. and Chapuis, G., J. Appl. Crystallogr., 2007, vol. 40, p. 786. https://doi.org/10.1107/S0021889807007637
Sheldrick, G.M., Acta Crystallogr., Sect. A, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053273314026370
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Crystallogr., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726
Funding
This study was performed under financial support by the Russian Foundation for Basic Research (project nos. 19-33-90222, 20-43-596008), by the Ministry of Science and Higher Education of the Russian Federation (project no. FCHF-2020-0008), and by the Government of Perm Krai.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflict of interest.
Additional information
Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 9, pp. 1275–1280 https://doi.org/10.31857/S0514749221090068.
Rights and permissions
About this article
Cite this article
Tretyakov, N.A., Bashorina, N.V., Belozerova, A.I. et al. Reaction of Pyrrolooxazinetriones with Diphenylguanidine. Synthesis of Substituted Spiro[imidazole-4,2′-pyrroles]. Russ J Org Chem 57, 1423–1427 (2021). https://doi.org/10.1134/S1070428021090062
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428021090062