Abstract
An efficient procedure has been developed for the synthesis of 2-phenyl-1,3,4-oxadiazole derivatives with one or two pyrrolidin-1-yl substituents in the benzene ring via nucleophilic substitution of fluorine in 2-[(di)fluorophenyl]-1,3,4-oxadiazole on heating with pyrrolidine under solvent-free conditions.
REFERENCES
Baijika, P., Akash, M., Midhula, C.C., and Shadiha, S.K., Int. J. Adv. Res., 2018, vol. 6, p. 1114. https://doi.org/10.21474/IJAR01/6328
Nayak, S.G. and Poojary, B., Chem. Africa, 2019, vol. 2, p. 551. https://doi.org/10.1007/s42250-019-00084-9
Santus, M., Pharm. Chem. J., 1992, vol. 26, p. 164. https://doi.org/10.1007/BF00766459
Szczepankiewicz, B.G., Liu, G., Jae, H.-S., Tasker, A.S., Gunawardana, I.W., von Geldern, T.W., Gwaltney, S.L., Wu-Wong, J.R., Gehrke, L., Chiou, W.J., Credo, R.B., Alder, J.D., Nukkala, M.A., Zielinski, N.A., Jarvis, K., Mollison, K.W., Frost, D.J., Bauch, J.L., Hui, Y.H., Claiborne, A.K., Li, Q., and Rosenberg, S.H., J. Med. Chem., 2001, vol. 44, p. 4416. https://doi.org/10.1021/jm010231w
Meng, X.-D., Gao, L.-X., Wang, Z.-J., Feng, B., Zhang, C., Satheeshkumar, R., Li, J., Zhu, Y.-L., Zhou, Y.-B., and Wang, W.-L., Bioorg. Chem., 2021, vol. 116, article ID 105384. https://doi.org/10.1016/j.bioorg.2021.105384
Popova, N.A., Yushko, É.G., Krasovitskii, B.M., Minkin, V.I., Lyubarskaya, A.É., and Gol’dberg, M.L., Chem. Heterocycl. Compd., 1983, vol. 19, p. 22. https://doi.org/10.1007/BF00512808
Doroshenko, A.O., Skripkina, V.T., Posokhov, E.A., Obukhova, E.N., and Shershukov, V.M., Chem. Heterocycl. Compd., 1997, vol. 33, p. 865. https://doi.org/10.1007/BF02253043
Han, J. and Wei, Y.-H., J. Mol. Struct., 2010, vol. 968, p. 32. https://doi.org/10.1016/j.molstruc.2010.01.016
Hamciuc, C., Homocianu, M., and Hamciuc, E., J. Mol. Liq., 2021, vol. 336, article ID 116268. https://doi.org/10.1016/j.molliq.2021.116268
Buettelmann, B., Han, B., Knust, H., Koblet, A., and Thomas, A., Int. Patent Appl. Pub. no. WO2007/071598 A1, 2007; Chem. Abstr., 2007, vol. 146, no. 198672.
Zhang, D., Cao, X., Wu, Q., Zhang, M., Sun, N., Zhang, X., and Tao, Y., J. Mater. Chem. C, 2018, vol. 6, p. 3675. https://doi.org/10.1039/c7tc04969b
Zheng, Y., Batsanov, A.S., Jankus, V., Dias, F.B., Bryce, M.R., and Monkman, A.P., J. Org. Chem., 2011, vol. 76, p. 8300. https://doi.org/10.1021/jo201488v
Sheldon, R.A., Chem. Soc. Rev., 2012, vol. 41, p. 1437. https://doi.org/10.1039/C1CS15219J
Kamal, A., Srinivasulu, V., Seshadri, B.N., Markandeya, N., Alari, A., and Shankaraiah, N., Green Chem., 2012, vol. 14, p. 2513. https://doi.org/10.1039/C2GC16430B
Sarkar, A., Santra, S., Kundu, S.K., Hajra, A., Zyryanov, G.V., Chupakhin, O.N., Charushin, V.N., and Majee, A., Green Chem., 2016, vol. 18, p. 4475. https://doi.org/10.1039/C6GC01279E
Gierczyk, B., Zalas, M., Kazmierczak, M., Grajewski, J., Pankiewicz, R., and Wyrzykiewicz, B., Magn. Reson. Chem., 2011, vol. 49, p. 648. https://doi.org/10.1002/mrc.2804
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This study was performed under financial support by the Russian Science Foundation (project no. 18-73-10119-P).
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Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 7, pp. 767–770 https://doi.org/10.31857/S0514749222070102.
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Krinochkin, A.P., Shtaitz, Y.K., Savchuk, M.I. et al. Solvent-Free Synthesis of 2-[(Di)aminophenyl]-1,3,4-oxadiazoles. Russ J Org Chem 58, 1064–1066 (2022). https://doi.org/10.1134/S1070428022070181
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DOI: https://doi.org/10.1134/S1070428022070181