REGIOSELECTIVE SYNTHESIS OF 1-ALKYL-4-METHYLSEMITHIOGLYCOLURILS

Abstract

The regioselective reaction of 4,5-dihydroxy-1-methylimidazolidine-2-thione with 1-alkylureas was explored for the first time, providing the previously inaccessible 1-alkyl-4-methylsemithioglycolurils as the major products. We demonstrated that the interaction of the reactants was accompanied by the formation of isomeric 1-alkyl-6-methylsemithioglycolurils and several known compounds: 1-methyl- and 3-methylthiohydantoins, 1-methyl-1H-imidazole-2(3H)-thione, and 1,4-disubstituted glycolurils as minor products. The reaction of 4,5-dihydroxy-1-methylimidazolidine-2-thione with 1-isopropylurea also produced a mixture of 1,1'(1-methyl-2-thioxoimidazolidine-4,5-diyl)bis(3-isopropylurea) diastereomers.

Authors: Anton A. Galochkin*, Alisa E. Pavlovskaya, Vladimir V. Baranov,
Yuri A. Strelenko, Angelina N. Kravchenko