FIELD: organic chemistry.
SUBSTANCE: invention relates to a method of obtaining derivatives of 3,5-diarylisoxazoles of General formula (I), where R1 is selected from H, F, CF3, OMe; R2=H, CF3, NO2; R3=H, F, CF3; for use as an active substance in medicinal products for the treatment of oncological diseases, characterized be the following: a two-stage synthesis is carried out, where the reaction of 2-aryl-1,1-dibromocyclopropanes of general formula (II) is carried out at the first stage, where R1 is selected from H, F, CF3, OMe; R2=H, CF3, NO2; R3=H, F, CF3; with a nitrosating reagent in a polar solvent at a temperature of 30–35°C for 10–40 min, while the concentration of 2-aryl-1,1-dibromocyclopropane is 0.05–0.06 mol/l, and in the second stage, a Suzuki cross-coupling reaction of 3-aryl-5-bromisoxazoles with a total formula (III), where R1 is selected from H, F, CF3, OMe; R2=H, CF3, NO2; R3=H, F, CF3; with arylboronic acids in the presence of a palladium catalyst and a base in a polar solvent.
EFFECT: highly regioselective production of new 3,5-diarylisoxazoles including unsymmetrical structures with yields from 50 to 99%, depending on the substituents in the benzene rings.
10 cl, 1 tbl, 25 ex
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Authors
Dates
2023-08-17—Published
2021-07-07—Filed