Two general procedures were developed for the synthesis of chiral N mono , N,N´ di , N,N´N´´ tri , and N,N´,N´´,N´´´ tetraalkylglycolurils based on the reactions of 4,5 dihydroxy imidazolidin 2 ones or glyoxal with one or two moles of alkylureas, respectively, by acid catalysis. The reactions of N monoalkyl and N,N´ dialkylureas with glyoxal proceed regioselectively. The mechanism of these reactions was suggested and partly confirmed by quantum chemical calculations and experimental data. The enantiomeric separation of some chiral glycolurils by chiral phase HPLC was carried out for the first time.
The N-hydroxymethylation, N-acetylation, and N-acetoxymethylation of mono-, di-, and trialkylglycolurils by reaction with the electrophilic reagents formaldehyde and acetaldehyde have been studied. General methods have been developed for the preparation of mono-, di-, and tri-Nhydroxymethylglycolurils by treatment of differently substituted N-alkylglycolurils with formaldehyde (as hemiformal in methanol) and the synthesis of di-N-and tri-N-acetyl-or N-acetoxymethylglycolurils via the electrophilic substitution of hydrogen atoms for an acetyl group at the nitrogen or oxygen atoms in the hydroxymethyl groups of glycolurils using acetic anhydride. The regioselectivity of the reaction of the 2-t-Bu-and 2-c-C 6 H 11 -glycolurils with formaldehyde has been shown to yield a 4,6-di(hydroxymethyl) derivative. It was found that the hydroxymethylation of 2,4-and 2,6-dialkylglycolurils occurs regioselectively with a stoichiometric ratio of glycoluril to hemiformal and permits preparation of their mono-and dihydroxymethyl derivatives. The enantiomeric analysis of the obtained compounds has been carried out for the first time using HPLC on chiral phases. X-ray analysis has been carried out on the previously unreported racemic 2, 6-diacetoxymethyl-4,8-dimethylglycoluril.
Glycolurils in α-Ureidoand α-Aminoalkylation Reactions. Part 1. α-Ureidoalkylation of Sulfamides with N-(Hydroxymethyl)glycolurils. -Novel bi-, tri-, and tetracyclic fused systems combining glycouril and sulfamide fragments are prepared. Compound (II) shows a weak fungicidal activity. -(GAZIEVA*, G. A.; KRAVCHENKO, A. N.; TRUNOVA, N. S.; MAKHOVA, N. N.; Russ.
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