1,6-Dibenzylglycoluril for synthesis of deprotected glycoluril dimer

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Authors

ŠTANCL Marek KHAN Muhammad Shamsul Azim ŠINDELÁŘ Vladimír

Year of publication 2011
Type Article in Periodical
Magazine / Source Tetrahedron
MU Faculty or unit

Faculty of Science

Citation
Web http://www.sciencedirect.com/science/article/pii/S0040402011013226
Doi http://dx.doi.org/10.1016/j.tet.2011.08.097
Field Organic chemistry
Keywords glycolurils; deprotection; alkylation
Description 1,6-Dibenzylglycoluril is not accessible via classical condensation reaction between substituted urea and glyoxal. In this paper 1,6-dibenzylglycoluril was successfully prepared by alkylation of 1,6-diacetylglycoluril with benzylbromide for the first time. 1,6-Dibenzylglycoluril reacted with formaldehyde to give tetrabenzylglycoluril dimer. Deprotection of this dimer and the previously reported o-xylyleneglycoluril dimer was achieved by dissolving metal reduction, whereas propyleneglycoluril dimer was deprotected by action of potassium persulfate.
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