The cross coupling of 5'-ethynyllappaconitine with benzoic acid chlorides under the conditions of the Sonogashira reaction in benzene leads to the corresponding 5-alkynones. By condensation of the obtained 5'-alkynones with amidines, compounds with hybrid structure containing fragments of a diterpene alkaloid and pyrimidine were synthesized. The yields of the target compounds were 67–90%. The possibility of carrying out the cross coupling – condensation reaction as a one-pot synthesis is demonstrated.
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This work was supported by the Russian Science Foundation (project No. 18-13-00361).
Analytical and spectral studies were performed at the Chemical Research Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(12), 1131–1138
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Cheremnykh, K.P., Savel’ev, V.А., Shkurko, O.P. et al. Synthesis of hybrid molecules containing pyrimidine and diterpene alkaloid lappaconitine fragments. Chem Heterocycl Comp 54, 1131–1138 (2018). https://doi.org/10.1007/s10593-019-02404-w
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DOI: https://doi.org/10.1007/s10593-019-02404-w