While searching for pharmacologically active compounds among 4,5-dihydrooxazole derivatives of maleopimaric acid, we studied for the first time the reaction between allyl-substituted maleopimaric acid derivatives and aromatic nitrile oxides that were generated from oximes by oxidation with sodium hypochlorite with or without ultrasonication of the biphasic system. The reaction occurred under mild conditions and regiospecifically provided 4,5-dihydroisoxazol-5-ylmethyl derivatives of maleopimaric acid in 77–99% yields.
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Here and further the signals of stereoisomer B are given in parentheses and not listed separately.
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This work was performed with financial support from the Russian Academy of Sciences Presidium program No. 38 “The study of fundamental problems of synthesis and structure–activity relationships for the purpose of creating new compounds and materials”.
IR spectra, 1H and 13C NMR spectra, and mass spectra were recorded on instruments at the Collective Use Center “Chemistry”, Ufa Institute of Chemistry, Russian Academy of Sciences.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(8), 796–803
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Vafina, G.F., Mukhamed’yanova, A.A., Khanova, M.D. et al. Synthesis of 4,5-dihydroisoxazole derivatives of maleopimaric acid by 1,3-dipolar cycloaddition reaction between its allyl derivatives and aromatic nitrile oxides. Chem Heterocycl Comp 54, 796–803 (2018). https://doi.org/10.1007/s10593-018-2352-5
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DOI: https://doi.org/10.1007/s10593-018-2352-5