Synthesis and structure of 1,3-dialkyl-4-(sulfonylimino)imidazolidin-2-ones

Abstract

Keywords: 1-alkylsulfamides, 1,3-dialkyl-4-(alkylaminosulfonylimino)imidazolidin-2-ones, 4,5-dihydroxyimidazolidin-2-ones, 1,3-dimethyl-4-(benzenesulfonylimino)imidazolidin-2-one, X-ray structural analysis.Imidazolidin-2-one derivatives possess a broad spectrum of biological activity. In particular, hydantoins are used in medicine and agrochemistry as anticonvulsants [1, 2], anticancer preparations [3], fungicides [4], and herbicides [5]. On the other hand compounds containing a sulfamide fragment display bacteriostatic, hypoglycemic, diuretic, and herbicidal action [2, 6-8]. For several years the reactions of 4,5-dihydroxyimidazolidin-2-ones (DHI) with ureas and their hetero analogues have been among our scientific interests. Recently as a result of investigations carried out by us on the interaction of 1-alkyl and 1,3-dialkyl-DHI with sulfamide and amides of sulfonic acids, an unusual reaction has been detected [9] leading to 4,4'-sulfonyldiiminobis(1,3-dialkylimidazolidin-2-one) 1 and 4(5)-aryl(or alkyl)-sulfonyliminoimidazolidin-2-one 2, containing both pharmacophoric fragments. We later showed that the reaction of 1,3-dialkyl-DHI with aminoguanidine proceeds analogously with the formation of 1,3-dialkyl-4-guanidinoiminoimidazolidin-2-ones 3 [10]. N N O NSO 2 R 3 R 1 R 2 N N O R 1 NNHCNH 2 R 2 NH N N O R R NSO 2 N N N R O R 2 3 HCl 1 .With the aim of broadening the scope of the discovery, the reaction of 1,3-dialkyl-DHI 4a,b with 1-alkylsulfamides 5a-d under conditions analogous to the conditions of obtaining compounds 2 and 3 (methanol, HCl) (Scheme 1) has been investigated. __________________________________________________________________________________________

Synthesis and structures of 5(3H)-oxotetrahydro-1H-imidazo[4,5-c][1,2,5]thiadiazole 2,2-dioxides

“…The characteristics of compound 4b are consistent with those reported earlier. 12 4,6 Diethyl 1,3 dimethyl 5(3H) oxo and 3,4,6 triethyl 1 methyl 5(3H) oxotetrahydro 1H imidazo[4,5 c][1,2,5]thia diazole 2,2 dioxides (2b,i). 4,5 Dihydroxy 1,3 diethylimidazol idin 2 one (1c) (0.17 g, 1 mmol) and 1,3 dialkylsulfamide 5e or 5f (1 mmol) were dissolved in acetone (1.0 mL) in a Teflon tube.…”

“…The reaction of 1c afforded compound 2g along with 1,3 diethyl 4 (propylaminosulfonylimino) imidazolidin 2 one (4b), which have been described in our earlier study. 12 The 1 H NMR analysis of the reaction mixtures evaporated to dryness showed that the ratio of the bi (2g) to monocyclic (4b) products is 2 : 5. The ratio was estimated based on the integrated intensity ratio for the proton signals of the CH-CH groups of compound 2g at δ 5.32 and the signals of the cyclic CH 2 group of compound 4b at δ 4.48.…”

“…9,10 Tetrahydroimidazothiadiazoles 2c,d were synthesized in 45-63% yields by condensation of 1a,b with unsubstituted sulfamide at pH 5-6 and 60 °C. 8 More recently, 12 we have found that the acid catalyzed reac tions of 1 alkylsulfamides with DHIs in methanol afford compounds containing the imine bond, viz., 1,3 dialkyl 4 (alkylaminosulfonylimino)imidazolidin 2 ones 4a-h.…”