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.
| Original language | English |
|---|---|
| Pages (from-to) | 1019-1025 |
| Number of pages | 7 |
| Journal | Chemical Papers |
| Volume | 74 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - 1 Mar 2020 |
Keywords
- Benzylation
- Condensation
- Glycoluril
- Glyoxal
- Tetrabenzylglycoluril
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Sinitsyna, A. A., Il’yasov, S. G., Chikina, M. V., Eltsov, I. V., & Nefedov, A. A. (2020). A search for synthetic routes to tetrabenzylglycoluril. Chemical Papers, 74(3), 1019-1025. https://doi.org/10.1007/s11696-019-00941-4