Abstract
8-Aroyl-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-1,6,7-triones reacted with 2-sulfanylacetic acid to give 2-{[3-aroyl-4-hydroxy-1-(2-hydroxyethyl)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl]sulfanyl}acetic acids whose structure was confirmed by X-ray analysis.
REFERENCES
Mikhailovskii, A.G., Shklyaev, V.S., and Aleksandrov, B.B., Chem. Heterocycl. Compd., 1990, vol. 26, p. 674. https://doi.org/10.1007/BF00756422
Maslivets, A.N., Smirnova, L.I., Ivanenko, O.I., and Andreichikov, Yu.S., Russ. J. Org. Chem., 1995, vol. 31, p. 707.
Mashevskaya, I.V., Kol’tsova, S.V., Duvalov, A.V., and Maslivets, A.N., Chem. Heterocycl. Compd., 2000, vol. 36, p. 1118. https://doi.org/10.1023/A:1002710721427
Mashevskaya, I.V., Kol’tsova, S.V., and Maslivets, A.N., Chem. Heterocycl. Compd., 2001, vol. 37, p. 652. https://doi.org/10.1023/A:1011681211056
Kollenz, G., Theuer, R., Peters, K., and Peters, E.-M., J. Heterocycl. Chem., 2001, vol. 38, p. 1055. https://doi.org/10.1002/jhet.5570380508
Allam, Y.A. and Nawwar, G.A.M., Heteroat. Chem., 2002, vol. 13, p. 207. https://doi.org/10.1002/hc.10020
Maslivets, A.N. and Bozdyreva, K.S., Chem. Heterocycl. Compd., 2002, vol. 38, p. 1535. https://doi.org/10.1023/A:1022666116527
Maslivets, A.N. and Bozdyreva, K.S., Chem. Heterocycl. Compd., 2002, vol. 38, p. 1535. https://doi.org/10.1023/A:1022666116527
Polygalova, N.N. and Mikhailovskii, A.G., Chem. Heterocycl. Compd., 2005, vol. 41, p. 1178. https://doi.org/10.1007/s10593-005-0299-9
Maslivets, A.N. and Bozdyreva, K.S., Russ. J. Org. Chem., 2006, vol. 42, p. 463. https://doi.org/10.1134/S1070428006030249
Mashevskaya, I.V., Aliev, Z.G., Mazhukin, D.G., Popov, S.A., Tikhonov, A.Ya., and Maslivets, A.N., Russ. J. Org. Chem., 2008, vol. 44, p. 1189. https://doi.org/10.1134/S1070428008080149
Surikova, O.V., Mikhailovskii, A.G., and Vakhrin, M.I., Chem. Heterocycl. Compd., 2009, vol. 45, p. 1131. https://doi.org/10.1007/s10593-009-0396-2
Jain, R., Sharma, K., and Kumar, D., Tetrahedron Lett., 2012, vol. 53, p. 6236. https://doi.org/10.1016/j.tetlet.2012.09.013
Mikhailovskii, A.G., Yusov, A.S., and Gashkova, O.V., Russ. J. Org. Chem., 2016, vol. 52, p. 223. https://doi.org/10.1134/S1070428016020111
Chervyakov, A.V. and Maslivets, A.N., Russ. J. Org. Chem., 2016, vol. 52, p. 610. https://doi.org/10.1134/S1070428016040291
Maslivets, A.A. and Maslivets, A.N., Russ. J. Org. Chem., 2016, vol. 52, p. 914. https://doi.org/10.1134/S1070428016060282
Mikhailovskii, A.G., Yusov, A.S., and Gashkova, O.V., Russ. J. Org. Chem., 2017, vol. 53, p. 1222. https://doi.org/10.1134/S1070428017080103
Chervyakov, A.V. and Maslivets, A.N., Russ. J. Org. Chem., 2018, vol. 54, p. 512. https://doi.org/10.1134/S1070428018030235
Maslivets, A.A., Dmitriev, M.V., and Maslivets, A.N., Russ. J. Org. Chem., 2018, vol. 54, p. 1573. https://doi.org/10.1134/S1070428018100238
Tretyakov, N.A. and Maslivets, A.N., Russ. J. Org. Chem., 2020, vol. 56, p. 332. https://doi.org/10.1134/S1070428020020256
Tretyakov, N.A., Dmitriev, M.V., and Maslivets, A.N., Russ. J. Org. Chem., 2020, vol. 56, p. 935. https://doi.org/10.1134/S1070428020050292
Bergman, J. and Romero, I., J. Heterocycl. Chem., 2010, vol. 47, p. 1215. https://doi.org/10.1002/jhet.453
Al-Thebeiti, M.S. and El-Zohry, M.F., Phosphorus, Sulfur, Silicon, 1994, vol. 88, p. 251. https://doi.org/10.1080/10426509408036929
Leañez, J., Nuñez, J., García-Marchan, Y., Sojo, F., Arvelo, F., Rodriguez, D., Buscema, I., AlvarezAular, A., Bello Forero, J.S., Kouznetsov, V.V., and Serrano-Martín, X., Exp. Parasitol., 2019, vol. 198, p. 31. https://doi.org/10.1016/j.exppara.2019.01.011
CrysAlisPro, Agilent Technologies, 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/S0021889807029238
Sheldrick, G.M., Acta Crystallogr., Sect. C, 2015, vol. 71, 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. Crystallogr., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726
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This study was performed under financial support by the Perm Scientific and Educational Center “Rational Use of Earth’s Interior,” 2021.
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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 12, pp. 1784–1788 https://doi.org/10.31857/S0514749221120156.
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Tretyakov, N.A., Dmitriev, M.V. & Maslivets, A.N. Synthesis of 2-[(Pyrrol-2-yl)sulfanyl]acetic Acids by Reaction of Pyrrolo[2,1-c][1,4]oxazinetriones with 2-Sulfanylacetic Acid. Russ J Org Chem 57, 2067–2070 (2021). https://doi.org/10.1134/S1070428021120253
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DOI: https://doi.org/10.1134/S1070428021120253