Synthesis of 3',4'-dihydro-2H,2'H,5H-spiro [imidazolidine-4,1'-naphthalene]-2,5-dione and its derivatives (original) (raw)
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Kragujevac Journal of Science
A series of twenty two different imidazolidine-2,4-dione derivatives, divided according to their structure into five groups, including alkyl, alkenyl or aryl 5,5disubstituted hydantoins, spirohydantoins, and fused bicyclic and tricyclic hydantoins, was synthesized and examined for in vitro antimicrobial activity against 15 strains of bacteria and 4 strains of yeast. The antimicrobial activity was evaluated by the determination of the minimal inhibitory concentration (MIC) and the minimal microbicidal concentration (MMC) using the microdilution method. The assayed compounds exerted moderate antibacterial and weak antifungal activity. The antimicrobial activities were influenced by the structure and concentration of the tested compounds as well as the type of test microorganisms. The fused bicyclic hydantoin derivatives obtained by organoselenium induced intramolecular cyclization exhibited the highest inhibitory activity. The examined hydantoin derivatives seem as drug-like candidate...
Molecules, 2009
Hydantoins and their derivatives constitute a group of pharmaceutical compounds with anticonvulsant and antiarrhythmic properties, and are also used against diabetes. N-3 and C-5 substituted imidazolidines are examples of such products. As such, we have developed a synthesis of 2,4-dione and 2-thioxo-4-one imidazolidinic derivatives by reaction of amino acids with C-phenylglycine, phenyl isocyanate and phenyl isothiocyanate. Four amino-derivatives IG(1-4) and eight imidazolidinic derivatives, IM(1-8), were obtained in yields of 70-74%. The mass, infrared, 1 H and 13 C-NMR spectra of representative products are discussed.
Synthesis of New Imidazolidin 2 4 dione and 2 Thioxoimidazolidin
Hydantoins and their derivatives constitute a group of pharmaceutical compounds with anticonvulsant and antiarrhythmic properties, and are also used against diabetes. N-3 and C-5 substituted imidazolidines are examples of such products. As such, we have developed a synthesis of 2,4-dione and 2-thioxo-4-one imidazolidinic derivatives by reaction of amino acids with C-phenylglycine, phenyl isocyanate and phenyl isothiocyanate. Four amino-derivatives IG(1-4) and eight imidazolidinic derivatives, IM(1-8), were obtained in yields of 70-74%. The mass, infrared, 1 H and 13 C-NMR spectra of representative products are discussed.
Synthesis of 4,5-bifunctionally substituted imidazolidin-2-ones
Chemistry of Heterocyclic Compounds, 1993
It is shown that the reaction of readily available 4,5-dihydroxyimidazolidin-2-ones with hydrazoic or ptoluenesulfinic acid takes place stereo-and regioselectively and leads to the formation of 4, 5-diazido-or 4, 5di (p-toly lsulfony l) imidazolidin-2-ones. The example of 4, 5-diazidoimidazolidin-2-one is used to demonstrate the possibility of using compounds of this type for stereoselective introduction of substituents into the 4 and 5 positions of the imidazole ring. A convenient method of constructing the imidazolidine ring is to use a-oxoaldehydes or a-oxoketones with ureas [1, 2]. The 4,5-dihydroxyimidzolidin-2-ones [1] obtained as a result of this reaction are polyfunctional compounds and can be used as the parent substances for preparing various imidazole derivatives. However, thus far, only a small number of example of synthetic use of compounds I have been described, in particular, for the preparation of 4,5-bifunctionally substituted imidazolidin-2-ones, which are of considerable interest in connection with their various useful properties. Discovered among the indicated compounds have been tranquilizers [3], sedatives and soporifics [4], anticonvulsants [5], herbicides [6], steel corrosion inhibitors [7], components of explosives [8], cotton fabric modifiers [9, 10], etc. The synthesis of 4,5-bifunctionally substituted imidazolidin-2-ones is based on the reaction of compounds I with nucleophilic reactants in the presence of acid catalysts. Thus, the reaction of imidazolidines I with alcohols or with difluoramine forms 4,5-dialkoxy-[2, 4, 11] or 4,5-bis(difluoramino)imidazolidin-2-ones [12], respectively, and the reaction with ureas forms substituted 2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-diones [2, 13]. It should be noted that the series of 4,5-bifunctionally substituted imidazolidin-2-ones, which can be obtained by the reaction described, is very limited, this being due to frequently occurring side reactions, in particular, conversion of compounds I to the corresponding hydantoins [14] or aromatization of the reaction products with the formation of substituted imidazolidin-2-ones [2]. It was of interest to study the possibility of using compounds I to synthesize new types of 4,5-bifunctionally substituted imidazolidin-2-ones. Some of the results obtained are presented in this report. We showed that 4,5-dihydroxyimidazolidin-2-one (Ia) reacts with excess hydrazoic acid, generated in situ from sodium azide and hydrochloric acid, in water at 20~ resulting in the formation of trans-4,5-diazidoimidazolidin-2-one (IIa) in diastereomerically pure form in up to 90% yields. The yield of compound IIa depends on the duration of the reaction and is 49% when the reaction is carried out for 6.5 days, 55% for 12.5 days, 61% for 14.5 days, 77% for 17.5 days, and 90% for 24 days. Similarly, the reaction of 4,5-dihydroxy-l,3-dimethylimidazolidin-2-one (Ib) with excess hydrazoic acid yields trans-4,5-diazido-l,3-dimethylimidazolidin-2-one (IIb) with complete stereoselectivity. It should be noted that in the case of compound Ib, the reaction with HN 3 takes place much faster than in the case of imidazolidine Ia, and the yield of product of lib is 67 % after 5 days. D iazidoimidazolidin-2-one IIa with a total yield of 44 % was also obtained by reacting glyoxal with urea in water (50~ 7 h, pH 6.5) with subsequent addition of sodium azide and hydrochloric acid to the reaction mixture containing dihydroxymidazolidin-2-one Ia and holding of the mixture at 20~ for 13 days.
Journal of Molecular Structure-theochem, 2005
Configurational and conformational analysis were performed using ab initio and semi-empirical molecular orbital methods in order to obtain structural, electronic and energetic information about three previously synthesized imidazolidine derivatives, namely: 3-benzyl-5benzylidene-imidazolidine-2,4-dione (5), 3-benzyl-5-benzylidene-2-thioxo-imidazolidine-4-one (6), 5-benzylidene-3-(2-oxo-2-phenylethyl)-2-thioxo-imidazolidine-4-one (7) and other two new proposed imidazolidine derivatives: 3-benzyl-5-benzylidene-4-thioxoimidazolidine-2-one (8) and 3-benzyl-5-benzylidene-imidazolidine-2,4-dithione (9). Important aspects related to structure activity relationship are highlighted. q
Helvetica Chimica Acta, 2009
The 1-substituted 3-alkyl/aryl-3-aminoquinoline-2,4(1H,3H)-diones 1 react with alkyl/aryl isocyanates to give novel 3-alkyl/aryl-3-ureidoquinoline-2,4(1H,3H)-diones (ΒΌ N-(3-alkyl/aryl-1,2,3,4-tetrahydro-2,4-dioxoquinolin-3-yl)ureas) 2 and/or 3a-alkyl/aryl-3,3a,5,9b-tetrahydro-9b-hydroxy-1H-imidazo[4,5-c]quinoline-2,4-diones 3 in high yields. Compounds 2 and 3 rearrange by boiling in AcOH or concentrated HCl solution to give three different types of spiro[imidazolidine-4,3'-[3H]indole]-2,2'(1'H)-diones, i.e., 10, 11, and 12, depending on the kind of substituents at C(3) and C(3a), respectively. All compounds were characterized by 1 Hand 13 C-NMR and IR spectroscopy as well as by atmospheric-pressure chemical-ionization (APCI) mass spectra. The structures of compounds 11c and 12Al were investigated by single-crystal X-ray diffraction analysis.