共查询到20条相似文献,搜索用时 31 毫秒
1.
《Journal of organometallic chemistry》2006,691(12):2623-2630
New chiral N,N-bidentate ligands derived from substituted 2-(4-isopropyl-4-methyl-4,5-dihydro-1H-imidazol-5-one-2-yl)pyridines have been prepared and characterised by means of 1H, 13C NMR spectroscopy and optical rotation. Their Cu(II) complexes were characterized by means of elemental analysis, 1H NMR spectroscopy and MS. By means of X-ray diffraction, molecular geometry of the complex of 2-(1-methyl-4-isopropyl-4-methyl-4,5-dihydro-1H-imidazol-5-one-2-yl)pyridine with copper(II) chloride was determined. The complex exhibits heterochiral dimeric arrangement of two square pyramids with one terminal and one bridge-forming chlorine atoms and two nitrogen atoms in the bases of the pyramids. The tops of these pyramids are formed by the remaining chlorine atoms. The complexes prepared catalyse the Henry reaction with the overall yields of 41-97% and with the maximum enantioselective excess of 19%. 相似文献
2.
A. G. Majouga E. K. Beloglazkina O. V. Shilova A. A. Moiseeva N. V. Zyk 《Russian Chemical Bulletin》2009,58(7):1392-1399
Tetradentate N4-type organic ligands containing two 5-(2-pyridylmethylidene)-2-thio-3,5-dihydro-4H-imidazol-4-one fragments linked by two-, four-, or six-carbon polymethylene bridges between the sulfur atoms were synthesized.
Mono- and dinuclear complexes of these ligands with copper(II) chloride, as well as with copper(I) and copper(II) perchlorates,
were prepared. The structure of the coordination compound (5Z,5′Z)-2,2′-(butane-1,2-diyl-disulfanyldiyl)bis-5-(2-pyridylmethylidene)-3-phenyl-3,5-dihydro-4H-imidazol-4-one with copper(I) perchlorate was established by X-ray diffraction. The copper atom in this complex is in a distorted
tetrahedral coordination formed by four nitrogen atoms of two imidazole and two pyridine rings. The perchlorate anion is located
in the outer sphere of the complex and is not involved in the coordination with the copper ion. The electrochemical study
of the ligands and the complexes was carried out by cyclic voltammetry and rotating disk electrode voltammetry. The initial
reduction of the complexes under study occurs at the metal atom. The length of the polymethylene bridge in the ligand has
only a slight effect on the redox properties of the ligands and the complexes. 相似文献
3.
《Tetrahedron letters》2004,45(41):7723-7726
New ligands and their complexes with iron(III) chloride have been suggested and prepared: (R,S)-, (R,R)- and (S,S)-2,6-bis(1-benzyl-4-isopropyl-4-methyl-4,5-dihydro-1H-imidazol-5-on-2-yl) pyridines. Both the ligands and their complexes were characterised by 1H and 13C NMR spectroscopy, optical rotation and X-ray diffraction. 相似文献
4.
Michael M. Bishop Leonard F. Lindoy Mary McPartlin Andrew Parkin Oliver T. Thorn-Seshold Peter Turner 《Polyhedron》2007
The synthesis and X-ray structures of four neutral copper(II) complexes and one cationic complex incorporating bidentate alkyl N-(4-oxo-5,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)imidocarbamate ligands are reported. The neutral complexes, which possess potential doublet (DA) hydrogen bonding motifs, form supramolecular structures based on synthons involving hydrogen bonding or phenyl embraces. The formation of sheets within the crystal through combination of these synthons, and the occurrence of guest molecules trapped in cavities between the sheets, are described. The cationic complex forms an extended hydrogen-bonded structure that incorporates nitrate ions. The structures of the five complexes are compared with others reported previously for complexes of related ligands. 相似文献
5.
A. V. Yudina A. G. Mazhuga E. K. Beloglazkina I. V. Yudin I. A. Rodin N. V. Zyk 《Russian Chemical Bulletin》2011,60(10):2120-2123
A reaction of potassium ({(4Z)-4-[(1-methyl-1H-imidazol-2-yl)methylene]-5-oxo-1-phenyl-4,5-dihydro-1H-imidazol-2-yl}thio)acetate with copper(II) chloride in methanol leads to bis(5-anilino-7-methoxycarbonyl-1-methyl-1H-imidazo[1,2-c]pyrimidin-4-ium) tetrachloro-cuprate(II), whose structure was confirmed by the X-ray diffraction studies. 相似文献
6.
The acylation of substituted 2-aminopropanamides with (2S)-Boc-proline, (2S)-Cbz-proline and (2S)-Bn-proline was used to prepare substituted 1-protected N-(1-carbamoyl-1,1-dialkyl-methyl)-(S)-prolinamides (74-89%), whose subsequent deprotection gave N-(1-carbamoyl-1,1-dialkyl-methyl)-(S)-prolinamides (94-95%). The enantiomerically pure N-(1-carbamoyl-1,1-dialkyl-methyl)-(S)-prolinamides obtained were tested as organocatalysts for the aldol reaction of cyclohexanone with 4-nitrobenzaldehyde, with yields ranging from 38% to 79% ee. The highest enantioselectivity (89% ee) was achieved by catalysis with N-(1-carbamoyl-cyclopentyl)-(S)-prolinamide (methanol, l0% HCl). By the action of sodium methoxide, Boc-N-(1-carbamoyl-cyclopentyl)-(S)-prolinamide was quantitatively cyclised to 2-(1-Boc-pyrrolidin-2-yl)-1,3-diazaspiro[4.4]non-1-en-4-one, which was accompanied by racemisation at the stereogenic centre of the proline skeleton. Alternatively, the substituted 4,4-dialkyl-2-pyrrolidin-2-yl-4,5-dihydro-1H-imidazol-5-ones were prepared by oxidation of 4,4-dialkyl-2-((2S)-1-Boc-pyrrolidin-2-yl)-4,5-dihydro-1H-imidazolidin-5-ones (54-69%). In an acid medium, 2-pyrrolidin-2-yl-1,3-diazaspiro[4.4]non-1-en-4-one and (4S)-4-isopropyl-4-methyl-2-pyrrolidin-2-yl-4,5-dihydro-1H-imidazol-5-one underwent racemisation. Conversely, the free base of (2S)-2-pyrrolidin-2-yl-1,3-diazaspiro[4.4]non-1-en-4-one very easily underwent oxidation to give the achiral 2-(4,5-dihydro-3H-pyrrol-2-yl)-1,3-diazaspiro[4.4]non-1-en-4-one. 相似文献
7.
Chandan Adhikary Rajesh Bera Buddhadeb Dutta Sreyashi Jana Gabriele Bocelli Andrea Cantoni Siddhartha Chaudhuri Subratanath Koner 《Polyhedron》2008
Three copper(II) Schiff-base complexes, [Cu(L1)(H2O)](ClO4) (1), [Cu(L2)] (2) and [Cu(L3)] (3) have been synthesized and characterized [where HL1 = 1-(N-ortho-hydroxy-acetophenimine)-2-methyl-pyridine], H2L2 = N,N′-(2-hydroxy-propane-1,3-diyl)-bis-salicylideneimine and H2L3 = N,N′-(2,2-dimethyl-propane-1,3-diyl)-bis-salicylideneimine]. The structure of complex 1 has been determined by single crystal X-ray diffraction analysis. In complex 1, the copper(II) ion is coordinated to one oxygen atom and two nitrogen atoms of the tridentate Schiff-base ligand, HL1. The fourth coordination site of the central metal ion is occupied by the oxygen atom from a water molecule. All the complexes exhibit high catalytic activity in the oxidation reactions of a variety of olefins with tert-butyl-hydroperoxide in acetonitrile. The catalytic efficacy of the copper(II) complexes towards olefin oxidation reactions has been studied in different solvent media. 相似文献
8.
Elena K. Beloglazkina Alexander G. MajougaRenata B. Romashkina Anna A. MoiseevaNikolai V. Zyk 《Polyhedron》2007
A series of S-alkylated derivatives of 2-thiohydantoins, containing two 5-(3-pyridylmethylene)-3,5-dihydro-4H-imiazole-4-one fragments joined by polymethylene bridges with different numbers of carbon atoms, was synthesized. The title (5Z,5′Z)-2,2′-(alkane-α,ω-diylsulfanyldiyl)bis(5-(3-pyridylmethylene)-3,5-dihydro-4H-imidazol-4-ones) (L) were obtained by alkylation of 5-(3-pyridylmethylene)-3-phenyl-2-thiohydantoine by 1,2-dibromoethane, 1,6-dibromohexane or 1,10-dibromodecane in DMF in the presence of potassium carbonate. The complexes of ligands L with CoCl2 · 6H2O have been synthesized. It is shown that, regardless of the L:CoCl2 ratio, complexes with LCoCl2 composition are obtained in all cases. The structure of the cobalt(II) chloride complex with (5Z,5′Z)-2,2′-(ethane-1,2-diyldisulfanyldiyl)bis(5-(3-pyridylmethylene)-3-phenyl-3,5-dihydro-4H-imidazol-4-one) was determined by means of the RSA method. The cobalt atom in this complex has a tetrahedral ligand environment and it is coordinated by two chloride anions and two nitrogen atoms of pyridine fragments, forming a 19-membered metallocycle. Electrochemical investigations of the synthesized ligands and complexes have been made by CVA and RDE methods. It is established that the first stage of reduction for the complexes takes place on the metal, whereas the first stage of oxidation takes place on the coordinated chloride-anions. 相似文献
9.
The paper describes preparation of a chiral bidentate ligand - 2-(2-bromophenyl)-4,5-dihydro-1H-imidazol-5-one, and a tridentate ligand - 2-bromo-1,3-bis(4,5-dihydro-1H-imidazol-5-on-2-yl)benzene, whose oxidative addition reaction with Pd(0) giving neutral organopalladium(II) complexes has been studied. The structure of these complexes was studied by means of NMR spectroscopy and X-ray diffraction. After transformation of the neutral organopalladium(II) complexes into the corresponding ionic species the latter were studied as enantioselctive catalysts for asymmetric Friedel-Crafts alkylation and Michael addition. 相似文献
10.
E. K. Beloglazkina A. V. Shimorsky A. G. Mazhuga O. V. Shilova V. A. Tafeenko N. V. Zyk 《Russian Journal of General Chemistry》2009,79(7):1504-1508
Cu(ClO4)2·6H2O was shown to react with 2,2′-[propane-1,3-diylbis(thio-2-phenylnemethylidene]-bis(3-pyridylamine) (I) or (5Z)-2-ethoxycarbonylmethyl-(2-pyridylmethylidene)-3,5-dihydro-4H-imidazol-4-one (II) in the presence of CH3CN with the reduction of copper(II) to copper(I) and the formation of the tetrahedral complex CuI(CH3CN)4ClO4 (III). In the course of the reaction the organic ligands I and II were oxidized to the corresponding sulfoxides. 相似文献
11.
V. O. Topuzyan L. G. Arutyunyan A. A. Oganesyan 《Russian Journal of Organic Chemistry》2007,43(6):868-871
4-Arylmethylidene-4,5-dihydro-1,3-oxazol-5-ones reacted with hexamethyldisilazane in ethyl acetate, acetonitrile, or DMF at room temperature to give mainly 2-acylamino-3-arylmethylideneprop-2-enamides, whereas in boiling DMF the corresponding 4-arylmethylidene-4,5-dihydro-1H-imidazol-5-ones were formed. The reaction of 2-benzoylamino-3-phenylprop-2-enamide with hexamethyldisilazane also led to the formation of 4-benzylidene-2-phenyl-4,5-dihydro-1H-imidazol-5-one, while its reaction with chlorotrimethylsilane afforded either a 1:1 mixture of 4-benzylidene-2-phenyl-4,5-dihydro-1,3-oxazol-5-one and 4-benzylidene-2-phenyl-4,5-dihydro-1H-imidazol-5-one or only the latter, depending on the solvent. 相似文献
12.
Pavel Drabina Jiří Hanusek Robert Jirásko Miloš Sedlák 《Transition Metal Chemistry》2006,31(8):1052-1056
New 2,6-bis(5-alkyl-1,5-dimethyl-4,5-dihydro-1H-imidazol-4-on-2-yl)pyridines have been prepared and characterized by 1H-, 13C-NMR and elemental analysis. These ligands form complexes with FeCl2, which were isolated and characterized by elemental analysis and MS. Both in the solid phase and in aqueous and methanolic
solutions the complexes have two ligand molecules per one ferrous ion. By means of the kinetic stopped-flow method, the rate
constants of acid catalyzed decomposition, which proceeds as a system of two consecutive reactions, were determined. It was
found that increasing steric demands of 5-alkyl substituent in the 4,5-dihydro-1H-imidazol-4-one cycle significantly retards the acid catalyzed solvolysis. The methyl derivative is solvolyzed cca two orders faster than the corresponding t-Bu derivative. 相似文献
13.
ukasz Balewski Franciszek Sczewski Patrick J. Bednarski Lisa Wolff Anna Nadworska Maria Gdaniec Anita Kornicka 《Molecules (Basel, Switzerland)》2020,25(24)
The appropriate 1-arylhydrazinecarbonitriles 1a–c are subjected to the reaction with 2-chloro-4,5-dihydro-1H-imidazole (2), yielding 7-(4,5-dihydro-1H-imidazol-2-yl)-2-aryl-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-imines 3a–c, which are subsequently converted into the corresponding amides 4a–e, 8a–c, sulfonamides 5a–n, 9, ureas 6a–I, and thioureas 7a–d. The structures of the newly prepared derivatives 3a–c, 4a–e, 5a–n, 6a–i, 7a–d, 8a–c, and 9 are confirmed by IR, NMR spectroscopic data, as well as single-crystal X-ray analyses of 5e and 8c. The in vitro cytotoxic potency of these compounds is determined on a panel of human cancer cell lines, and the relationships between structure and antitumor activity are discussed. The most active 4-chloro-N-(2-(4-chlorophenyl)-7-(4,5-dihydro-1H-imidazol-2-yl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)benzamide (4e) and N-(7-(4,5-dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)-[1,1′-biphenyl]-4-sulfonamide (5l) inhibits the growth of the cervical cancer SISO and bladder cancer RT-112 cell lines with IC50 values in the range of 2.38–3.77 μM. Moreover, N-(7-(4,5-dihydro-1H-imidazol-2-yl)-2-phenyl-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)-4-phenoxybenzenesulfonamide (5m) has the best selectivity towards the SISO cell line and induces apoptosis in this cell line. 相似文献
14.
Hassan Keypour Maryam Shayesteh Sadegh Salehzadeh Laura Valencia 《Journal of organometallic chemistry》2008,693(19):3179-3187
Two new potentially hexadentate N2O4 Schiff base ligands 2-((z)-(2-(2-(2-((z)-3,5-di-tert-butyl-2-hydroxybenzylideneamino) phenoxy) phenoxy) phenylimino) methyl)-4,6-di-tert-butylphenol [H2L1] and 2-((z)-(2-(2-(2-((z)-3,5-di-tert-butyl-2-hydroxybenzylideneamino) phenoxy)-5-tert-butylphenoxy) phenylimino) methyl)-4,6-di-tert-butylphenol [H2L2] were prepared from the reaction of 3,5-di-tert-butyl-2-hydroxy benzaldehyde with 1,2-bis(2′-aminophenoxy)benzene or 1,2-bis(2′-aminophenoxy)-4-t-butylbenzene, respectively. From the direct reaction of ligands [H2L1] and [H2L2] with copper(II) and cobalt(II) salts in methanolic solution and in the presence of N(Et)3 the neutral [CuL1], [CuL2], [CoL1] and [CoL2] complexes were prepared. All complexes were characterized by IR spectra, elemental analysis, magnetic susceptibility, mass spectra, molar conductance (Λm), UV-Vis spectra and in the case of [CuL2] with X-ray diffraction. X-ray crystal structure of [CuL2] showed that the complex contains copper(II) in a distorted square planar environment of N2O2 donors. Three CH/π interactions were observed in the molecular structure of latter complex. 相似文献
15.
V. O. Topuzyan V. M. Kazoyan R. A. Tamazyan A. G. Aivazyan L. Kh. Galstyan 《Russian Journal of Organic Chemistry》2018,54(9):1369-1377
ω-[(4Z)-2-Aryl-4-arylmethylidene-5-oxo-4,5-dihydro-1H-imidazol-1-yl]alkanoic acids were synthesized by reaction of N-substituted α,β-dehydropeptides with chloro(trimethyl)silane or 1,1,1,3,3,3-hexamethyldisilazane. Both initial peptides and (4H)-imidazol-5-one derivatives based thereon were tested for anticholinesterase activity. 相似文献
16.
E. S. Barskaia A. A. Beloglazkina B. Wobith N. A. Zefirov A. G. Majouga E. K. Beloglazkina N. V. Zyk S. A. Kuznetsov O. N. Zefirova 《Russian Chemical Bulletin》2015,64(7):1560-1563
A series of 2-aryl-5-arylmethylidene-1,3-oxazol-5(4H)-ones and 2-aryl-5-arylmethylidene-N-methyl-3,5-dihydro-4H-imidazol-4-ones was synthesized as structural analogs of combret- astatin A-4 (a compound possessing antitumor activity). (5Z)-5-[(4-Methoxyphenyl)methyl-idene]-3-methyl-2-(4-methylphenyl)-3,5-dihydro-4H-imidazol-4-one was found to exhibit the highest cytotoxicity against cells of human A549 lung carcinoma line (EC50 = 6±0.8 μmol L?1). 相似文献
17.
R. I. Vas’kevich A. I. Vas’kevich E. B. Rusanov V. I. Staninets M. V. Vovk 《Russian Journal of Organic Chemistry》2013,49(1):123-129
Intramolecular electrophilic cyclization of 6-allylsulfanylpurine by the action of iodine and arenesulfenyl chlorides gave 7-iodomethyl-7,8-dihydro[1,3]thiazolo[2,3-i]purin-6-ium pentaiodide and 7-arylsulfanylmethyl-7,8-dihydro[1,3]thiazolo[2,3-i]purin-6-ium perchlorates, respectively. 7-Iodomethyl-7,8-dihydro-[1,3]thiazolo[2,3-i]purin-6-ium iodide reacted with sodium and potassium alkoxides to produce alkyl N-[5-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-4-yl]formimidates, and its reaction with secondary cyclic amines afforded 5-(4-methyl-1,3-thiazol-2-yl)-N-[morpholin-4-yl(or piperidin-1-yl)methylidene]-1H-imidazol-4-amines. Successive treatment of 7-arylsulfanylmethyl-7,8-dihydro[1,3]thiazolo[2,3-i]purin-6-ium perchlorates with sodium acetate and morpholine led to the formation of 5-(4-arylsulfanylmethyl-4,5-dihydro-1,3-thiazol-2-yl)-N-(morpholin-4-ylmethylidene)-1H-imidazol-4-amines. 相似文献
18.
Michail N. Elinson Anatolii N. Vereshchagin Nikita O. Stepanov Pavel A. Belyakov Gennady I. Nikishin 《Tetrahedron letters》2010,51(50):6598-6601
Cascade assembly of N,N′-dialkylbarbituric acids and aldehydes in the presence of bromine leads to the selective and efficient formation of substituted 1,5-dihydro-2H,2′H-spiro(furo[2,3-d]pyrimidine-6,5′-pyrimidine)-2,2′,4,4′,6′-(1′H,3H,3′H)-pentones in 70-88% yields via a complex cascade process. Spirobarbiturates containing the furo[2,3-d]pyrimidine framework are a class of compounds with interesting pharmacological and physiological activity. 相似文献
19.
1,1,2,2-tetraaminoethane derivatives: III. Condensation of 2-(Dinitromethylene)imidazolidine-4,5-diol with nitrogen-containing nucleophiles 总被引:1,自引:0,他引:1
E. V. Sizova V. V. Sizov I. V. Tselinskii 《Russian Journal of Organic Chemistry》2007,43(8):1232-1237
Condensation of 1,1-diamino-2,2-dinitroethylene with glyoxal and formaldehyde in water solutions at pH 7–8 gave rise to 2-(dinitromethylene)imidazolidine-4,5-diol and 1,1-diamino-N,N′-bis(hydroxymethyl)-2,2-dinitroethylene respectively. Condensation products of 2-(dinitromethylene)imidazolidine-4,5-diol with acetonitrile, benzonitrile, urethane, 3,4-diaminofurazan were isolated. The reaction of 4,5-diacetamido-2-(dinitromethylene) imidazolidine sulfate with water in acetonitrile led to the formation of 2-(dinitromethylene)-5-methyl-1,2,3,3a,4,6a-hexahydroimidazo[4,5-d]imidazole. The dehydration of 2-(dinitromethylene)imidazolidine-4,5-diol in a system H2SO4-AcOH provided 2-(dinitromethylene)-2,3-dihydro-1H-imidazol-4-ol. 1,1-Diamino-N,N′-bis(hydroxymethyl)-2,2-dinitroethylene in sulfuric acid was converted into 4-(dinitromethylene)-1,3,5-oxadiazinane. 相似文献
20.
A reaction of 3-allyl- and 3-phenylthiohydantoins with 1,5-diphenyl- and 1-phenyl-substituted 3-formyl-2-pyrazolines was used to obtain a series of 5-(pyrazolin-3-ylmethylidene)-2-thioxotetrahydro-4H-imidazol-4-ones, the subsequent alkylation of which with methyl iodide or ethyl chloroacetate gave the corresponding 2-alkylthio-5-(pyrazolin-3-ylmethylidene)-3,5-dihydro-4H-imidazol-4-ones in the yields from 30 to 77%. The oxidation of (5Z)-3-phenyl-5-[(1,5-diphenylpyrazolin-3-yl)methylidene]-2-methylsulfanyl-4,5-dihydroimidazol-4-one with lead tetraacetate led to the corresponding pyrazole in 48% yield. 相似文献