Abstract
In this study, a search for synthetic routes to never-before-seen tetrabenzylglycoluril was made and two synthetic strategies were examined: condensation of 1,3-dibenzylurea with glyoxal, and N-alkylation of glycoluril and its disubstituted derivative. The first synthetic approach furnished only a condensation product, 3,3′-bi(6,8-dibenzyl-2,4-dioxa-9,8-diazabicyclo[3.3.0]octan-7-one, bearing the dioxolane moiety, in 24% yield. The second method in which 2,6-dibenzylglycoluril was reacted with BnCl in acetonitrile in the presence of KOH for 3 h afforded the target product tetrabenzylglycoluril in over 60% yield.
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Acknowledgements
This work was performed using instruments provided by the Biysk Regional Center for Shared Use of Scientific Equipment of the SB RAS (IPCET SB RAS, Biysk).
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Sinitsyna, A.A., Il’yasov, S.G., Chikina, M.V. et al. A search for synthetic routes to tetrabenzylglycoluril. Chem. Pap. 74, 1019–1025 (2020). https://doi.org/10.1007/s11696-019-00941-4
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DOI: https://doi.org/10.1007/s11696-019-00941-4