Abstract
8-Aroyl-3,4-dihydro-1Н-pyrrolo[2,1-с][1,4]oxazine-1,6,7-triones reacts with N-ethylaniline with formation of N-phenyl-N-ethylammonium 3′-aroyl-1′-(2-hydroxyethyl)-2,5′-dioxo-1-ethyl-1′,5′-dihydrospiro[indoline-3,2′-pyrrol]-4′-oates, which, at acidification, are converted into 3′-aroyl-4′-hydroxy-1′-(2-hydroxyethyl)-1-ethylspiro[indoline-3,2′-pyrrole]-2,5′(1′H)-diones, the structure of both classes of products was confirmed by X-ray diffraction.
REFERENCES
Theodorescu, D., Patent US 2014315894A1, 2014.
Feder, M., Patent Poland WO 2015189799A1, 2015.
Han, Y., Wu, Q., Sun, J., and Yan, C.-G., Tetrahedron, 2012, vol. 68, no. 41, p. 8539. https://doi.org/10.1016/j.tet.2012.08.030
Sarkar, R. and Mukhopadhyay, C., Tetrahedron Lett., 2013, vol. 54, no. 28, p. 3706. https://doi.org/10.1016/j.tetlet.2013.05.017
Saha, M. and Das, A.R., ChemistrySelect, 2017, vol. 2, no. 31, p. 10249. https://doi.org/10.1002/slct.201701989
Vydzhak, R.N. and Panchishin, S.Y., Russ. J. Gen. Chem., 2011, vol. 81, no. 3, p. 617. https://doi.org/10.1134/S1070363211030340
Gein, V.L., Gein, L.F., Kuznetsova, E.D., Sheptukha, M.A., Tsypliakova, E.P., and Potiemkin, K.D., Chem. Heterocycl. Compd., 2008, vol. 44, no. 5, p. 626. https://doi.org/10.1007/s10593-008-0085-6
Babenysheva, A.V. and Maslivets, A.N., Russ. J. Org. Chem., 2008, vol. 44, no. 9, p. 1401. https://doi.org/10.1134/S1070428008090297
Tutynina, N.M., Maslivets, V.A., and Maslivets, A.N., Russ. J. Org. Chem., 2014, vol. 50, no. 3, p. 454. https://doi.org/10.1134/S1070428014030300
CrysAlisPro, Rigaku Oxford Diffraction, 2022, Version 1.171.42.74a.
Sheldrick, G.M., Acta Crystallogr. (A), 2015, vol. 71, no. 1, p. 3. https://doi.org/10.1107/S2053273314026370
Sheldrick, G.M., Acta Crystallogr. (C), 2015, vol. 71, no. 1, p. 3. https://doi.org/10.1107/S2053229614024218
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Cryst., 2009, vol. 42, no. 2, p. 339. https://doi.org/10.1107/S0021889808042726
Tretyakov, N.A., Dmitriev, M.V., and Maslivets, А.N., Russ. J. Org. Chem., 2020, vol. 56, no. 8, p. 1367. https://doi.org/10.1134/S1070428020080060
Funding
The work was carried out with financial support from the Ministry of Education and Science of the Russian Federation (project no. FSNF-2023-0004).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
No conflict of interest was declared by the authors.
Additional information
Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Tretyakov, N.A., Shaginurova, A.I., Dmitriev, M.V. et al. Synthesis of Spiro[indoline-pyrroles] by the Reaction of Pyrrolooxazinetriones with N-Ethylaniline. Russ J Gen Chem 94, 532–538 (2024). https://doi.org/10.1134/S107036322403006X
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S107036322403006X