We report the first example of the direct nucleophilic C–H functionalization of cyclic aldonitrone, a derivative of 2H-imidazole 1-oxide, with 1H-imidazole and 3,5-dimethylpyrazole rings using oxidative C–N cross-coupling reactions in the presence of palladium(II) catalyst. The obtained new bisheterocyclic N-oxides may be of interest as molecules with potential biological activity and as functional organic materials.
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This study received financial support from the Russian Science Foundation (grant No. 18-73-00088).
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Supplementary information file containing 1Н and 13С NMR spectra of compounds 3, 5, as well as twodimensional 1H –13C HSQC and 1H –13C HMBC spectra and X-ray structural analysis dataset for compound 3 is available from the journal website at http://link.springer.com/journal/10593.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(8), 783–787
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Akulov, A.A., Varaksin, M.V., Charushin, V.N. et al. The First Example of Palladium(II)-Catalyzed Oxidative C–N Cross Coupling of 2H-Imidazole 1-Oxide with Azoles. Chem Heterocycl Comp 55, 783–787 (2019). https://doi.org/10.1007/s10593-019-02536-z
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DOI: https://doi.org/10.1007/s10593-019-02536-z