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

Abstract

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.

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Funding

This work was financially supported by the National Academy of Sciences of Belarus (grant X18UKA-011).

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Correspondence to T. S. Khlebnikova.

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Khlebnikova, T.S., Piven’, Y.A., Isakova, V.G. et al. One-Pot Synthesis of Trifluoromethyl-Substituted Imidazobenz[1,2-d]- and -[1,2-c]isoxazoles. Russ J Gen Chem 90, 746–749 (2020). https://doi.org/10.1134/S1070363220040295

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Keywords:

  • 8-trifluoromethyl-4,5-dihydro-3H-imidazo[4',5':5,6]benz[1,2-d]isoxazoles
  • 8-trifluoromethyl-4,5-dihydro-3H-imidazo[4',5':3,4]benz[1,2-c]isoxazoles
  • one-pot synthesis
  • 3-trifluromethyl-6,7-dihydrobenz[d]isoxazolones
  • 3-trifluromethyl-6,7-dihydrobenz[c]isoxazolones