Abstract
The reaction of 5-substituted 4-(2,2,2-trichloroacetyl)furan-2,3-diones with substituted benzohydrazides, thiophene-2-carbohydrazide, or 2-phenylacetohydrazide in anhydrous chloroform on stirring for several hours afforded 1-substituted 3-aryl(heteroaryl)-5-hydroxy-4-(2,2,2-trichloroacetyl)-4,5-dihydro-1H-pyrazole5-carboxylic acids as mixtures of two diastereoisomers at a ratio of about 70:30.
REFERENCES
Mashkovskii, M.D., Lekarstvennye sredstva (Medicines), Moscow: Novaya Volna, 2012, 16th ed., pp. 164, 185.
Sun, Y. and Chen, J.D.Z., Curr. Neuropharmacol., 2012, vol. 10, p. 212. https://doi.org/10.2174/157015912803217297
Karrouchi, K., Radi, S., Ramli, Y., Taoufik, J., Mabkhot, Y.N., Alaizari, F.A., and Ansar, M., Molecules, 2018, vol. 23, article no. 134. https://doi.org/10.3390/molecules23010134
Chandrakantha, B., Isloor, A.M., Shetty, P., Isloor, S., Malladi, S., and Fun, H.K., Med. Chem. Res., 2012, vol. 21, p. 2702. https://doi.org/10.1007/s00044-011-9796-9
Akbas, E., Berber, I., Sener, A., and Hasanov, B., Farmaco, 2005, vol. 60, p. 23. https://doi.org/10.1016/j.farmac.2004.09.003
Viale, M., Anzaldi, M., Aiello, C., Fenoglio, C., Albicini, F., Emionite, L., Gangemi, R., and Balbi, A., Pharm. Rep., 2013, vol. 65, p. 717. https://doi.org/10.1016/S1734-1140(13)71050-8
Castagnolo, D., De Logu, A., Radi, M., Bechi, B., Manetti, F., Magnani, M., Supino, S., Meleddu, R., Chisu, L., and Botta, M., Bioorg. Med. Chem., 2008, vol. 16, p. 8587. https://doi.org/10.1016/j.bmc.2008.08.016
Girish, Y.R., Kumar, K.S.S., Manasa, H.S., and Shashikanth, S., J. Chin. Chem. Soc., 2014, vol. 61, p. 1175. https://doi.org/10.1002/jccs.201400170
Gosselin, F., O’Shea, P.D., Webster, R.A., Reamer, R.A., Tillyer, R.D., and Grabowski, E.J.J., Synlett, 2006, vol. 2006, no. 19, p. 3267. https://doi.org/10.1055/s-2006-956487
Ohtsuka, Y., Uraguchi, D., Yamamoto, K., Tokuhisa, K., and Yamakawa, T., Tetrahedron, 2012, vol. 68, p. 2636. https://doi.org/10.1016/j.tet.2012.01.075
Martins, M.A.P., Pereira, C.M.P., Beck, P., Machado, P., Moura, S., Teixeira, M.V.M., Bonacorso, H.G., and Zanatta, N., Tetrahedron Lett., 2003, vol. 44, p. 6669. https://doi.org/10.1016/S0040-4039(03)01633-2
He, S., Chen, L., Niu, Y.-N., Wu, L.-Y., and Liang, Y.-M., Tetrahedron Lett., 2009, vol. 50, p. 2443. https://doi.org/10.1016/j.tetlet.2009.03.030
Delaunay, T., Genix, P., Es-Sayed, M., Vors, J.-P., Monteiro, N., and Balme, G., Org. Lett., 2010, vol. 12, p. 3328. https://doi.org/10.1021/ol101087j
Dadiboyena, S., Valente, E.J., and Hamme, A.T., Tetrahedron Lett., 2009, vol. 50, p. 291. https://doi.org/10.1016/j.tetlet.2008.10.145
Yadav, J.S., Subba Reddy, B.V., Srinivas, M., Prabhakar, A., and Jagadeesh, B., Tetrahedron Lett., 2004, vol. 45, p. 6033. https://doi.org/10.1016/j.tetlet.2004.06.031
Xie, F., Cheng, G., and Hu, Y., J. Comb. Chem., 2006, vol. 8, p. 286. https://doi.org/10.1021/cc050159d
Ilhan, Ö.I., Sarıpınar, E., and Akçamur, Y., J. Heterocycl. Chem., 2005, vol. 42, p. 117. https://doi.org/10.1002/jhet.5570420117
Sener, A., Kasimogullari, R., Sener, M.K., and Genc, H., Chem. Heterocycl. Compd., 2004, vol. 40, p. 1039. https://doi.org/10.1023/B:COHC.0000046695.00178.79
Souza, F.R., Fighera, M.R., Lima, T.T.F., Bastiani, J., Barcellos, I.B., Almeida, C.E., Oliveira, M.R., Bonacorso, H.G., Flores, A.E., and Mello, C.F., Pharmacol. Biochem. Behav., 2001, vol. 68, p. 525. https://doi.org/10.1016/S0091-3057(01)00453-1
Souza, F.R., Souza, V.T., Ratzlaff, V., Borges, L.P., Oliveira, M.R., Bonacorso, H.G., Zanatta, N., Martins, M.A.P., and Mello, C.F., Eur. J. Pharmacol., 2002, vol. 451, p. 141. https://doi.org/10.1016/S0014-2999(02)02225-2
Clark, E.L., US Patent no. 3636214, 1969.
Si, Sh., Li, Zh., Zheng, Zh., Yang, Y., Liu, Z., Shao, H., Guo, H., Jiang, W., and He, X., CN Patent no. 101711760A, 2010.
Lisovenko, N.Yu., Chemadurov, D.G., Balandina, S.Yu., and Makhmudov, R.R., Pharm. Chem. J., 2017, vol. 51, p. 191. https://doi.org/10.1007/s11094-017-1580-9
Balandina, S.Yu., Maksimov, A.Yu., Lisovenko, N.Yu., and Shilova, A.V., Russ. J. Biopharm., 2019, vol. 11, p. 63.
Myshkina, O.A., Balandina, S.Yu., Makhmudov, R.R., Dmitriev, M.V., and Lisovenko, N.Yu., Russ. Chem. Bull., Int. Ed., 2021, vol. 70, p. 1408. https://doi.org/10.1007/s11172-021-3232-1
Lisovenko, N.Yu., Nasibullina, E.R., Kharitonova, S.S., and Myshkina, O.A., Synthesis, 2021, vol. 53, p. 1955. https://doi.org/10.1055/s-0040-1705998
Lisovenko, N.Yu., Nasibullina, E.R., and Dmitriev, M.V., Russ. Chem. Bull., Int. Ed., 2019, vol. 68, p. 578. https://doi.org/10.1007/s11172-019-2457-8
Becker, H.G.O., et al., Organikum. Organisch-chemisches Grundpraktikum, Weinheim: Wiley, 2004, 22nd ed.
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 financially supported by the world-level Perm Scientific and Educational Center “Rational Use of the Earth Interior,” 2023.
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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 6, pp. 762–771 https://doi.org/10.31857/S0514749223060046.
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Kharitonova, S.S., Nasibullina, E.R., Ivanov, D.V. et al. Recyclization of 5-Substituted 4-(2,2,2-Trichloroacetyl)furan-2,3-diones with (Het)Arenecarbohydrazides. Russ J Org Chem 59, 993–999 (2023). https://doi.org/10.1134/S1070428023060040
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DOI: https://doi.org/10.1134/S1070428023060040