Imidazolidine Ring Research Articles

(1,3-Dimethylimidazolidine-2-selone-κSe)bis(1,10-phenanthroline-κ2N,N′)copper(II) bis(perchlorate) and bis(2,2′-bipyridyl-κ2N,N′)(imidazolidine-2-thione-κS)copper(II) bis(perchlorate)

In the first title salt, [Cu(C(12)H(8)N(2))(2)(C(5)H(10)N(2)Se)](ClO(4))(2), the Cu(II) centre occupies a distorted trigonal-bipyramidal environment defined by four N donors from two 1,10-phenanthroline (phen) ligands and by the Se donor of a 1,3-dimethylimidazolidine-2-selone ligand, with the equatorial plane defined by the Se and by two N donors from different phen ligands and the axial sites occupied by the two remaining N donors, one from each phen ligand. The Cu-N distances span the range 1.980 (10)-2.114 (11) A and the Cu-Se distance is 2.491 (3) A. Intermolecular pi-pi contacts between imidazolidine rings and the central rings of phen ligands generate chains of cations. In the second salt, [Cu(C(10)H(8)N(2))(2)(C(3)H(6)N(2)S)](ClO(4))(2), the Cu(II) centre occupies a similar distorted trigonal-bipyramidal environment comprising four N donors from two 2,2'-bipyridyl (bipy) ligands and an S donor from an imidazolidine-2-thione ligand. The equatorial plane is defined by the S donor and two N donors from different bipy ligands. The Cu-N distances span the range 1.984 (6)-2.069 (7) A and the Cu-S distance is 2.366 (3) A. Intermolecular pi-pi contacts between imidazolidine and pyridyl rings form chains of cations. A major difference between the two structures is due to the presence in the second complex of two N-H...O hydrogen bonds linking the imidazolidine N-H hydrogen-bond donors to perchlorate O-atom acceptors.

1-[(6-Chloropyridin-3-yl)methyl]-3-phenylimidazolidine-2,4-dione

In the title compound, C15H12ClN3O2, the imidazolidine ring system is almost planar; the dihedral angles between it and the phenyl and pyridine rings are 74.44 (12) and 83.75 (12)°, respectively. The structure is stabilized by weak C—H⋯O hydrogen bonds, as well as C—H⋯π inter­actions.

Phenyl 2-oxoimidazolidine-1-carboxylate

In the title compound, C10H10N2O3, the five-membered imidazolidine ring is planar, with an r.m.s. derivation of 0.0243 (1)A. The dihedral angle between the imidazolidine ring and the phenyl ring is 78.83 (2)°. A centrosymmetric ring is formed by a pair of N—H⋯O hydrogen bonds, creating a dimer; C—H⋯O hydrogen bonds connect these dimers into a three-dimensional network.

Novel route for synthesizing hyperbranched polyamine

AbstractA novel route for the synthesis of hyperbranched polyamine containing imidazolidine rings was developed, proceeding by the step‐growth polymerization of acrolein with ethylene diamine. The reaction kinetics and polymerization mechanism were studied with NMR and ultraviolet–visible spectroscopy. The influence of the reaction temperature and the concentration and feed ratio of the reactants on the structural characteristics of the obtained products was investigated. To obtain stable hyperbranched polyamines as analogues of hyperbranched poly(ethylene imine) or dendrimeric poly(propylene imine), sodium borohydride was used to reduce the synthesized hyperbranched polyamines to open the imidazolidine rings. The molecular weights, degrees of branching, and glass‐transition temperatures of the hyperbranched polyamines before and after reduction were compared. The polymerization behaviors of acrolein with other amines such as ethanol amine, propylene diamine, and 1,6‐hexane diamine were also investigated. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 699–708, 2007

Two-step α-ureidoalkylation of ureas with 4,5-dihydroxyimidazolidin-2-ones

Two-step α-ureidoalkylation of ureas with various 4,5-dihydroxyimidazolidin-2-ones gave novel 1,3-dialkyl-4,5-bis(3-alkylureido)-, 1,3-dialkyl-4,5-bis[3-(2-pyrimidyl)ureido]-, or 1,3-dialkyl-4,5-bis(3,3-dialkylureido)imidazolidin-2-ones and ensembles of three imidazolidine rings. The structure of 4,5-bis(2-oxoimidazolidin-1-yl)imidazolidin-2-one was confirmed by X-ray diffraction data.

Synthesis and Crystal Structure of 3-Ethyl-2-(ethylthio)-5-(4-oxo-4H-chromen-3-yl methylene)imidazolidine-4-one

The structure of the title compound, C17H16N2O3S, was prepared by the reaction of chromone-3-carboxaldehyde with 2-thioxo-imidazolidine-4-one and ethyl iodide. The five-membered imidazolidine ring is in a planar conformation with a maximum deviation of 0.013(1)A, and making a dihedral angle of 5.36(5)° with the benzopyran ring system. The crystal structure is stabilized by intra and intermolecular hydrogen-bond interactions.

3-Ethyl-5-(4-oxochroman-3-ylmethylene)-1,3-imidazolidine-2,4-dione

The mol­ecule of the title compound, C15H12N2O4, is planar, with a dihedral angle of 0.97 (4)° between the planes of the five-membered imidazolidine and benzopyran ring systems. The crystal structure is stabilized by C—H⋯O and N—H⋯O hydrogen-bonding inter­actions.

4,4,5,5-Tetramethyl-2-(2-thienyl)imidazolidine-1,3-diol

In the title compound, C11H18N2O2S, the dihedral angle between the thio­phene ring and the mean plane of the puckered imidazolidine ring is 85.0 (2)°. Adjacent mol­ecules are linked by pairs of inversion-related O—H⋯N hydrogen bonds, leading to a chain structure.

Copper Complex of an Iminodioxabicyclo[3.3.1]nonane Pendant Ligand: The First Example of Iminodioxocin Bridgehead Nitrogen Coordination

The pentadentate N4O amine-imine-naphthol ligand (HL(D)) containing rigid 8,16-imino-8H,16H-dinaphtho[2,1-b:2,1-f][1,5]dioxocin is formed preferentially, under visible light irradiation conditions, instead of the product H3L, expected from imidazolidine ring formation. A strained chelate bite enforces the first bridgehead nitrogen coordination to a copper(II) ion from the bicyclic iminodioxocin part of the ligand as shown by X-ray crystallography.

Chiral Imidazolinium Salts: Lewis Acids, Shift Reagents and Ionic Liquids

Using standard methodology for imidazolidine ring synthesis, new chiral mono- and bis-imidazolinium salts have been prepared in good to excellent yields. The final step involves quaternization and counter anion exchange. These salts show good catalytic activity in aza-­Diels-Alder reactions; however, no asymmetric induction was observed. Tested as chiral shift reagents, the bis-imidazolinium salts were able to resolve the 19F and 1H NMR signals belonging to the two enantiomers of the potassium salt of Mosher’s acid.

The First Synthesis of Assemblies of Imidazolidine Rings by α‐Ureidoalkylation of Imidazolidin‐2‐one with 4,5‐Dihydroxyimidazolidin‐2‐ones.

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1-[5-(4-Fluorophenyl)-1,2-oxazol-3-ylmethyl]-2-nitroiminoimidazolidine

In the title compound, C13H12FN5O3, the five-membered imidazolidine ring adopts an envelope conformation. The mol­ecular structure is stabilized by an intra­molecular N—H⋯O hydrogen bond. The crystal structure shows C—H⋯O and C—H⋯N inter­actions.

(1,3-Benzothiazol-2-yl)[1-(2-chlorobenzyl)imidazolidin-2-ylidene]amine

In the crystal structure of the title compound, C17H15ClN4S, the benzothiazole, imidazolidine and benzene rings are twisted relative to each other.

Dinuclear Copper(II) Complexes of a Macrocyclic Compartmental Ligand in Two Isomeric Forms. Exogenous Ion Effect upon Ligand Isomerism

Abstract A dinucleating compartmental ligand derived from the cyclic [2:1:1] condensation of 2,6-diformyl-4-methylphenol, 1,3-propanediamine, and diethylenetriamine (dien) assumes two isomeric forms in the dinuclear copper(II) complexes, [Cu2(La)](ClO4)2·2H2O (1) and [Cu2(Lb)(AcO)]BPh4 (2). Complex 1 has the ligand in the usual condensation with a trimethylene chain (–(CH2)3–) and a 3-azapentamethylene chain (–(CH2)2NH(CH2)2–) between two azomethine nitrogen atoms; the nitrogen atom of the 3-azapentamethylene chain is free from coordination. Complex 2 has the ligand in an unusual condensation with dien: The central amino nitrogen of dien is further involved in the condensation with one C=N linkage to form an imidazolidine ring. An acetate ion bridges two copper ions to form a μ-acetato-di(μ-phenolato) dinuclear core with a saddle-like shape. The origin for the unusual condensation in 2 is considered and the physicochemical properties of 1 and 2 are examined.

Crystal structures of substituted imidazolidine derivatives

The crystal structures of isoxazole, 3-[[dihydro-2-[(Z)-2-oxohyrazono]-1H-imidazol-1-(3H)-yl]methyl-5-phenyl-,N-oxide] (C13H13N5O3) (I), isoxazole,3-[[dihydro-2-[(Z)-2-oxohyrazono]-1H-imidazol-1-(3H)-yl]-methyl-5-(4-methylphenyl)-,N-oxide] (C14H15N5O3) (II) and isoxazole, 3-[[dihydro-2-[(Z)-2-oxohyrazono]-1H-imidazol-1-(3H)-yl]-methyl-5-(2-methoxyphenyl)-,N-oxide] (C14H15N5O4) (III) have been determined by X-ray diffraction studies. The compound I, crystallized in triclinic space group $$P\bar 1$$ with unit cell dimensions a = 7.2405(7) A, b = 7.9936(8) A, c = 11.6573(11) A, α = 97.801(2)°, β = 90.884(2)°, γ = 96.250(2)° and Z = 2. Compound II crystallized in orthorhombic space group Pna21 with unit cell dimensions a = 10.1778(10) A, b = 28.228(3) A, c = 5.1206(5) A, and Z = 4. Compound III crystallized in monoclinic space group P21/n with unit cell dimensions a = 7.8439(9) A, b = 7.8544(9) A, c = 23.534(3) A, β = 99.464(2)° and Z = 4. For all three compounds, the five-membered imidazolidine ring adopts an envelope conformation. The crystal structures are stabilized by both the intramolecular N–H···O and intermolecular N–H···N hydrogen bonding.

Atmospheric CO 2 fixation leads to a unique [formula omitted] bridged [formula omitted] complex and coordination induced ligand hydrolysis to a [Cu II] complex

Atmospheric CO 2 fixation in basic medium (initial pH 8.5) leads to a novel hydrogencarbonate single-oxygen bridged dicopper(II) complex [ Cu 2 II ( L ) ( HCO 3 ) ] · 4 H 2 O ( 1 · 4 H 2 O ) from the dinucleating ligand H 3L (2-methyl-2-(2′-hydroxyphenyl)-1,3-bis[4-methyl-4-(2-hydroxyphenyl)-3-azabut-3-enyl]-1,3-imidazolidine). The same reaction in neutral medium (initial pH 6) gives the monocopper(II) complex [Cu II(HL 1)] · 2ClO 4 ( 2) of the zwitterionic ligand (HL 1), following 2-(2′-hydroxyphenyl) imidazolidine ring and terminal (2-hydroxyphenyl)methylimine hydrolysis. Both 1 · 4H 2O and 2 have been characterized by IR and UV–Vis spectroscopy, conductivity measurements and X-ray crystallography. Variable temperature (2–300 K) magnetic measurements show that complex 1 · 4H 2O exhibits weak intramolecular antiferromagnetic coupling.

Thermal properties of polyurethanes and polyacrylates with trioxoimidazolidine rings

New polyurethanes and polyacrylates containing imidazolidine rings were obtained from N,N'-bis(2-hydroxyalkyl)parabanates and Izocyn T-80 or acrylic and methacrylic acid, respectively. The polymers show usually higher thermal stability or heat resistance in comparison with their analogues obtained from aliphatic diols or classic polyacrylates.

IDENTIFICATION OF A NOVEL IN VITRO METABONATE FROM LIVER MICROSOMAL INCUBATIONS

In vitro drug metabolism studies during the early drug discovery stage are becoming increasingly important. With the increasing demand for high throughput and quick turnaround time for in vitro metabolism studies, however, careful examination of the results and proper design of the experiments are still crucial. In this communication, we report the identification and mechanism of formation of a novel metabonate from incubations of a diamine-containing compound with liver microsomes. The metabonate appeared to be the major product, and its formation was NADPH- and microsomal protein-dependent. Liquid chromatography/mass spectrometry and NMR analysis of the metabonate indicated an extra carbon and unusual formation of an imidazolidine ring. Further studies revealed that this metabonate was not a true biotransformation product from the diamine compound itself in the microsomal incubation, but rather a product resulting from a condensation reaction between the compound and a metabolite of the solvent (alcohol) used in the incubation. When the microsomal incubations contained a small amount of methanol or ethanol as solvent, the alcohols were metabolized to formaldehyde or acetaldehyde, which then condensed with the diamine compound through an imine intermediate to form the metabonate. The compound itself was metabolically stable in vitro when acetonitrile or dimethyl sulfoxide was used as solvent. During the study of in vitro microsomal stability and metabolite identification of amine-containing compounds, the use of alcohol as solvent should be avoided.

The first synthesis of assemblies of imidazolidine rings by α-ureidoalkylation of imidazolidin-2-one with 4,5-dihydroxyimidazolidin-2-ones

The synthesis of assemblies of imidazolidine rings has been developed based on the α-ureidoalkylation of imidazolidin-2-one with 4,5-dihydroxyimidazolidin-2-ones.

Microbial hydroxylation of imidacloprid for the synthesis of highly insecticidal olefin imidacloprid

Microorganisms that bring about the aerobic transformation of imidacloprid (IMI) were isolated and screened, and the microbial regio- and stereoselective hydroxylation of IMI was studied. Some bacteria and fungi transformed IMI to 5-hydroxyl IMI. Bacterium Stenotrophomonas maltophilia CGMCC 1.1788 resting cells transformed IMI into R-5-hydroxyl IMI at the highest conversion rate. The enzyme catalyzed the stereoselective hydroxylation at position C12 of IMI in the imidazolidine ring. Under acidic conditions, 5-hydroxyl IMI was converted into olefin IMI in high molar conversion yield. The olefin IMI exhibited about 19 and 2.2 times more insecticidal efficacy than IMI against horsebean aphid imago and nymph, respectively, and about 1.4 times more active than IMI against brown planthopper imago. The transformation rate of IMI by resting cells of S. maltophilia CGMCC 1.1788 was promoted significantly by some carbohydrates and organic acids. The reaction medium with 5% sucrose resulted in 8.3 times greater biotransformation yield as compared with that without sucrose.