Examples



mdbootstrap.com



 
Статья
2020

One-Pot Synthesis of Trifluoromethyl-Substituted Imidazobenz[1,2-d]- and -[1,2-c]isoxazoles


T. S. KhlebnikovaT. S. Khlebnikova, Yu. A. Piven’Yu. A. Piven’, V. G. IsakovaV. G. Isakova, V. A. SmaliakV. A. Smaliak, A. V. BaranovskyA. V. Baranovsky, F. A. LakhvichF. A. Lakhvich
Российский журнал общей химии
https://doi.org/10.1134/S1070363220040295
Abstract / Full Text

Synthesis of regioisomeric 8-trifluoromethyl-4,5-dihydro-3H-imidazo[4',5':5,6]benz[1,2-d]isoxazoles and 8-trifluoromethyl-4,5-dihydro-3H-imidazo[4',5':3,4]benz[1,2-c]isoxazolones was realized by one-pot oxidation of 3-trifluromethyl-6,7-dihydrobenz[d]- or [c]isoxazoles with selenium dioxide in glacial acetic acid followed by a condensation of formed in situ 3-trifluromethyl-6,7-dihydrobenz[d]- or [c]isoxazole-4,5-diones with benzaldehydes in the presence of ammonium acetate.

Author information
  • Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 220141, Minsk, BelarusT. S. Khlebnikova, Yu. A. Piven’, V. G. Isakova, V. A. Smaliak, A. V. Baranovsky & F. A. Lakhvich
References
  1. Zhang, H.-Z., Zhao, Z.-L., and Zhou, C.-H., Bioorg. Med. Chem., 2018, vol. 26, no. 12, p. 3065. https://doi.org/10.1016/j.bmc.2018.05.013
  2. Lamberth, C., J. Heterocycl. Chem., 2018, vol. 55, no. 9, p. 2035. https://doi.org/10.1002/jhet.3252
  3. Rakesh, K.P., Shantharam, C.S., Sridhara, M.B., Manukumar, H.M., and Guin, H.-L., MedChemComm., 2017, vol. 8, no. 11, p. 2023. https://doi.org/10.1039/c7md00449d
  4. Wang, J., Sánchez-Roselló, M., Aceña, J.L., del Pozo, С., Sorochinsky, A.E., Fustero, S., Soloshonok, V.A., and Liu, H., Chem. Rev., 2014, vol. 114, no. 4, p. 2432. https://doi.org/10.1021/cr4002879
  5. Zhou, Y., Wang, J., Gu, Z., Wang, S., Zhu, W., Aceña, J.-L., Soloshonok, V. A., Izawa, K., and Liu, H., Chem. Rev., 2016, vol. 116, no. 2, p. 422. https://doi.org/10.1021/acs.chemrev.5b00392
  6. Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications, Petrov, V.A., Ed., New Jersey: John Willey and Sons, 2009.
  7. Kumar, V., and Kaur, K., J. Fluorine Chem., 2015, vol. 180, p. 55. https://doi.org/10.1016/j.jfluchem.2015.09.004
  8. Jeschke, P., Pest. Manag. Sci., 2017, vol. 73, no. 6, p. 1053. https://doi.org/10.1002/ps.4540
  9. Khlebnicova, T.S., Piven’, Yu.A., Isakova, V.G., Baranovsky, A.V., Lakhvich, F.A., Sorochinsky, A.E., and Gerus, I.I., J. Heterocycl. Chem., 2018, vol. 55, no. 7, p. 1791. https://doi.org/10.1002/jhet.3218
  10. Ali, I., Lone, M.N., and Aboul-Enein, H.Y., MedChemComm., 2017, vol. 8, no. 9, p. 1742. https://doi.org/10.1039/C7MD00067G
  11. Fan, Y.-L., Jin, X.-H., Huang, Z.P., Yu, H.-F., Zeng, Z.-G., Gao, T., and Feng, L.-S., Eur. J. Med. Chem., 2018, vol. 150, p. 347. https://doi.org/10.1016/j.ejmech.2018.03.016
  12. Tahlan, S., Kumar, S., and Narasimhan, B., BMC Chem., 2019, vol. 13. Article no. 18, p. 1. https://doi.org/10.1186/s13065-019-0521-y
  13. Narasimhan, B., Sharma, D., and Kumar, P., Med. Chem. Res., 2012, vol. 21, no. 3, p. 269. https://doi.org/10.1007/s00044-010-9533-9
  14. Khlebnikova, T.S., Piven’, Yu.A., Baranovskii, A.V., and Lakhvich, F.A., Russ. J. Org. Chem., 2013, vol. 49, no. 3, p. 421. https://doi.org/10.1134/S1070428013030184
  15. Khlebnicova, T.S., Isakova, V.G., Baranovsky, A.V., Borisov, E.V., and Lakhvich, F.A., J. Fluorine Chem., 2006, vol. 127, p. 1564. https://doi.org/10.1016/j.jfluchem.2006.08.003
  16. Khlebnikova, T.S., Isakova, V.G., and Lakhvich, F.A., Russ. J. Org. Chem., 2009, vol. 45, no. 7, p. 993. https://doi.org/10.1134/S1070428009070033