Synthesis and Structure of 1-Substituted Semithioglycolurils

Abstract

Two methods for the synthesis of previously unavailable 1-substituted semithioglycolurils were developed. These methods consist of the cyclocondensation of 1-substituted ureas with 4,5-dihydroxy- or 4,5-dimethoxyimidazolidine-2-thione or glyoxal, followed by the reaction of the resulting 1-substituted 4,5-dihydroxyimidazolidine-2-ones with HSCN in a two-step one-pot procedure. Two of the desired semithioglycolurils were obtained as conglomerates.

Synthesis, Structures and Antifungal Activity of Selenoglycolurils

“…Our design strategy focused on exchange of S for Se within the thioglycoluril scaffold where it was envisaged that transforma-tion of the C=S group into C=Se could be achieved in 2 steps through the formation of 2-(methylthio)-5-oxo-3,3a,4,5,6,6ahexahydroimidazo [4,5-d]imidazol-1-ium iodides, akin to the synthesis of 2-selenothymidine [15] or 2-selenouridine. [16] The parent thioglycolurils 1 a-r were prepared as previously described from variously substituted or unsubstituted 4,5dihydroxyimidazolidin-2-ones [17,18] or 4,5-dihydroxyimidazolidine-2-thione. [18] Using procedures adapted from our previous synthesis of isothiouronium salts 2 a, 2 b, 2 g [19] extension of the methodology by S-methylation of compounds 1 a-r with 2 equiv.…”

“…[17,18] 1-Cyclohexyl-5thioxohexahydroimidazo [4,5-d]imidazol-2(1H)-one 1 m and 1phenyl-5-thioxohexahydroimidazo [4,5-d]imidazol-2(1H)-one 1 r were similarly prepared from 1-cyclohexyl-or 1-phenylurea and 4,5-dihydroxyimidazolidine-2-thione, respectively . [18] 1-Propylurea was obtained by previously reported procedure from PrNH 2 , hydrochloric acid, and KOCN. [18] 1,3-Dipropylurea was obtained by previously reported procedure from 1-propylurea and PrBr.…”

“…[18] 1-Propylurea was obtained by previously reported procedure from PrNH 2 , hydrochloric acid, and KOCN. [18] 1,3-Dipropylurea was obtained by previously reported procedure from 1-propylurea and PrBr. [35] The isothouronium salts 2 a, 2 b, 2 g were synthesized by S-methylation of compounds 1 a, 1 b, 1 g with MeI.…”

Reaction Pathway and Kinetic Study of 4,5-Dihydroxyimidazolidine-2-thione Synthesis by HPLC and NMR

“…The DHIT is a molecular building block to produce macrocyclic semithioglycolurils and semithiobambusurils, 2 strongly binds anions inside the macromolecule, and the presence of sulfur in the structure allows binding metal ions at their sulfur-edged portals that distinguishes them from the oxygencontaining bambusurils. 3,4 These properties allow them to be used to treat the channelopathies, in supramolecular chemistry, anion sensing and catalysis.…”

Synthesis and Crystal Structures of Novel Glycoluryl Carboxylic Acids Conglomerates

“…It is known that tetrahydroimidazo [4,5-d]imidazole-2,5(1H,3H)-diones (glycolurils) are capable of forming supramolecular assemblies and supermolecules of varying complexity upon crystallization from different solvents [9][10][11][12][13][14][15][16][17][18][19][20][21], which can lead to spontaneous resolution of racemates into enantiomers (conglomerate formation) [22][23][24][25][26]. Some glycolurilcarboxylic acids [16,17,20,21,24,25] also have such properties (Fig.…”