ChemInform Abstract: Synthesis and Structure of 1,3‐Dialkyl‐4‐(sulfonylimino)imidazolidin‐2‐ones.

Abstract

Imidazole derivatives R 0190Synthesis and Structure of 1,3-Dialkyl-4-(sulfonylimino)imidazolidin-2-ones. -A new reaction between imidazolidin-2-ones (I) and the urea heteroanalogues (II) is reported. The product yields show a correlation to the carbon chain length of the N-alkyl substituents in (I), while unsubstituted imidazolidines do not react. -(GAZIEVA, G. A.; LOZHKIN, P. V.; KRAVCHENKO, A. N.; LYSENKO, K. A.; KOLOTYRKINA, N. G.; MAKHOVA, N. N.; Chem. Heterocycl. Compd. (N. Y.) 43 (2007) 8, 981-988; Zelinsky Inst. Org. Chem., Russ. Acad. Sci., Moscow 117913, Russia; Eng.) -H. Haber 16-130

α-Thioureidoalkylation of functionally substituted ureas: I. Tandem cyclization and esterification in reactions of N-(carboxyalkyl)ureas with 1,3-dialkyl-4,5-dihydroxy-4,5-diphenylimidazolidine-2-thiones in alcohols

“…In particular, reactions of N-alkyl- [9], N-(carboxyalkyl)- [10], N-(hydroxyalkyl)- [11], and N-(aminoalkyl)ureas [12] were reported. We recently described some specificities of the condensation of N-(carboxyalkyl)ureas with 4,5-dihydroxy-4,5-diphenylimidazolidin-2-ones: when these reactions were carried out in alcohols (methanol or propan-2-ol) the cyclization process leading to N-(carboxyalkyl)glycolurils was accompanied by esterification [13].…”

“…Reactions of ureas with 4,5-dihydroxy-4,5-diphenylimidazolidin-2- ones are usually carried out in water, lower alcohols, or their mixtures, depending on the solubility of the reactants, under conditions of acid catalysis (HCl) [9][10][11][12][13]. The condensation of acids Va-Vd with imidazolidinethiones IVa and IVb were performed by heating the reactants in boiling methanol or propan-2-ol (compounds IV are insoluble in water) in the presence of concentrated hydrochloric acid over a period of 1, 2, or 3 h. It was found that the formation of bicyclic thioglycolurils VIa-VIh was accompanied by esterification of the carboxy group [14] so that the major products were the corresponding methyl and isopropyl esters VIIa-VIIf and VIIIa-VIIIh (Scheme 1).…”

α-Thioureidoalkylation of functionally substituted ureas: II. Synthesis of thio analogs of N-hydroxyalkyl-1,5-diphenylglycolurils

“…Over several years we were interested in the chemistry of glycolurils (octahydroimidazo [4,5-d]imidazole-2.5-diones) [4][5][6][7][8][9] which constitute a new class of neurotropic compounds [10][11][12]. Furthermore, it is known that diphenylglycolurils containing alkyl substituents on the nitrogen atoms affect hepatic cytochrome P-450-dependent monooxygenase system [13].…”