N-Alkylation Reaction in the Synthesis of Tetra-Substituted Glycoluryls

A new method is suggested herein for the synthesis of tetrasubstituted glycolurils by treatment of disubstituted glycolurils (di-tert-butylglycolurils, di-isopropylglycoluril) with alkylating agents such as methyl iodide, ethyl bromide and benzyl chloride in acetonitrile in the presence of KOH. Opti...

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Bibliographic Details
Published in:Journal of Siberian Federal University. Chemistry 2020-01, Vol.13 (1), p.40-45
Main Authors: Sinitsyna, Anastasia А., Il’yasov, Sergey G.
Format: Article
Language:English
Subjects:
Acetonitrile
Alkylation
Benzyl bromide
Biological activity
Chemical synthesis
Chloride
Chlorides
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Summary:A new method is suggested herein for the synthesis of tetrasubstituted glycolurils by treatment of disubstituted glycolurils (di-tert-butylglycolurils, di-isopropylglycoluril) with alkylating agents such as methyl iodide, ethyl bromide and benzyl chloride in acetonitrile in the presence of KOH. Optimum conditions for the preparation of the target product in high yield were studied by the example of the synthesis of dibenzyl-di-tert-butylglycoluril: time 3 h and reaction temperature 75ºС at a 1:4 M/M molar ratio of disubstituted glycoluril to benzyl chloride. Thus, the target product yield was 83%. It was also found that benzyl chloride should be used as the alkylating agent because the product yield under the same equal conditions was higher with benzyl chloride than with benzyl bromide which in turn is more toxic and less available
ISSN:1998-2836
2313-6049
DOI:10.17516/1998-2836-0164