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1.
Patrik Pařík Josef Jansa Sylva Holešová Aleš Marek Věra Klimešová 《Journal of heterocyclic chemistry》2013,50(4):903-910
Reactivity of 2‐(4‐hydroxyphenyl)‐1H‐imidazoline and 2‐(4‐hydroxyphenyl)‐1H‐imidazole toward substituted phenyl isocyanates was studied. When mentioned imidazoline was treated with 2.5 equiv of substituted phenyl isocyanate, three N,O‐dicarboxamides were prepared (substituents are H, 4‐NO2, and 4‐CH3). Subsequently, N,O‐diacetylated 2‐(4‐hydroxyphenyl)‐1H‐imidazoline was prepared and selective deprotection method was developed for preparation of 1‐acetyl‐2‐(4‐hydroxyphenyl)‐1H‐imidazoline using diethylamine in acetone. Six carbamates derived from this imidazoline were then prepared using 1.1 equiv of substituted phenyl isocyanates (substituents are H, 4‐CH3, 4‐OCH3, 4‐NO2, 4‐CN, and 3‐CF3). Finally, two carbamates were prepared from 2‐(4‐hydroxyphenyl)‐1H‐imidazole (substituents are 4‐NO2 and 4‐CN). No reactivity to imidazole ring was observed in this case. Eight derivatives were subjected to antimycobacterial screening. Concurrently, reactivity of 2‐(2‐aminophenyl)‐ and 2‐(2‐hydroxyphenyl)‐1H‐imidazole toward aliphatic and aromatic isocyanates was studied. Eight ureas were prepared using equivalent mixture of 2‐(2‐aminophenyl)‐1H‐imidazole and isocyanate (Et, Pr, isoPr, terc‐Bu, Cy, Ph, 4‐CH3C6H4, 4‐CNC6H4). Similar attempts to obtain related carbamates from 2‐(2‐hydroxyphenyl)‐1H‐imidazole lead only to three substituted phenyl carbamates (substituents are 4‐CH3, 4‐NO2, and 4‐CN). In both cases, no reactivity to imidazole ring was observed again. 相似文献
2.
Rosa A. Vzquez García Sylvain Berns Ren Gutirrez Prez Marcos Martínez García 《Acta Crystallographica. Section C, Structural Chemistry》2002,58(10):o619-o620
In 2‐methyl‐1,4,5‐triphenyl‐1H‐imidazole, C22H18N2, the three substituent phenyl groups are not delocalized with the imidazole moiety; the dihedral angles these phenyl groups form with the imidazole ring are in the range 25.90 (5)–63.49 (6)°. 相似文献
3.
Jan W. Bats Peter Schell Joachim W. Engels 《Acta Crystallographica. Section C, Structural Chemistry》2013,69(5):529-533
Crystal structures are reported for three substituted 1H‐imidazole‐4,5‐dicarbonitrile compounds used as catalysts for the coupling reaction of nucleoside methyl phosphonamidites, namely 2‐(3′,5′‐dimethylbiphenyl‐2‐yl)‐1H‐imidazole‐4,5‐dicarbonitrile, C19H14N4, (I), 2‐(2′,4′,6′‐trimethylbiphenyl‐2‐yl)‐1H‐imidazole‐4,5‐dicarbonitrile, C20H16N4, (II), and 2‐[8‐(3,5‐dimethylphenyl)naphthalen‐1‐yl]‐1H‐imidazole‐4,5‐dicarbonitrile, C23H16N4, (III). The asymmetric unit of (I) contains two independent molecules with similar conformations. There is steric repulsion between the imidazole group and the terminal phenyl group in all three compounds, resulting in the nonplanarity of the molecules. The naphthalene group of (III) shows significant deviation from planarity. The C—N bond lengths in the imidazole rings range from 1.325 (2) to 1.377 (2) Å. The molecules are connected into zigzag chains by intermolecular N—H...Nimidazole [for (I)] or N—H...·Ncyano [for (II) and (III)] hydrogen bonds. 相似文献
4.
Yoshinobu Inouye Yoshiko Sakaino 《Acta Crystallographica. Section C, Structural Chemistry》2000,56(7):884-887
Red non‐solvate crystals of the title compound from ethanol, C23H19N3O4, orange solvate crystals from tert‐butanol, C23H19N3O4·C4H10O, yellow solvate crystals from dioxane–water, C23H19N3O4·0.5C4H8O2, and intense yellow solvate crystals from benzene–N,N′‐dimethylformamide, C23H19N3O4·C6H6, differ from each other in their molecular conformation and hydrogen‐bonding scheme. The bathochromic shifts of the crystal color are explained by the molecular planarity and charge‐transfer effect among the imidazole molecules. 相似文献
5.
《Acta Crystallographica. Section C, Structural Chemistry》2017,73(2):91-96
Subtle modifications of N‐donor ligands can result in complexes with very different compositions and architectures. In the complex catena‐poly[[bis{1‐[(1H‐benzotriazol‐1‐yl)methyl]‐1H‐imidazole‐κN 3}copper(II)]‐μ‐benzene‐1,3‐dicarboxylato‐κ3O 1,O 1′:O 3], {[Cu(C8H4O4)(C10H9N5)2(H2O)]·2H2O}n , each CuII ion is six‐coordinated by two N atoms from two crystallographically independent 1‐[(1H‐benzotriazol‐1‐yl)methyl]‐1H‐imidazole (bmi) ligands, by three O atoms from two symmetry‐related benzene‐1,3‐dicarboxylate (bdic2−) ligands and by one water molecule, leading to a distorted CuN2O4 octahedral coordination environment. The CuII ions are connected by bridging bdic2− anions to generate a one‐dimensional chain. The bmi ligands coordinate to the CuII ions in monodentate modes and are pendant on opposite sides of the main chain. In the crystal, the chains are linked by O—H…O and O—H…N hydrogen bonds, as well as by π–π interactions, into a three‐dimensional network. A thermogravimetric analysis was carried out and the fluorescence behaviour of the complex was also investigated. 相似文献
6.
《Acta Crystallographica. Section C, Structural Chemistry》2017,73(4):314-318
The unsymmetrical N‐heterocyclic ligand 1‐[(benzotriazol‐1‐yl)methyl]‐1H‐1,3‐imidazole (bmi) has three potential N‐atom donors and can act in monodentate or bridging coordination modes in the construction of complexes. In addition, the bmi ligand can adopt different coordination conformations, resulting in complexes with different structures due to the presence of the flexible methylene spacer. Two new complexes, namely bis{1‐[(benzotriazol‐1‐yl)methyl]‐1H‐1,3‐imidazole‐κN 3}dibromidomercury(II), [HgBr2(C10H9N5)2], and bis{1‐[(benzotriazol‐1‐yl)methyl]‐1H‐1,3‐imidazole‐κN 3}diiodidomercury(II), [HgI2(C10H9N5)2], have been synthesized through the self‐assembly of bmi with HgBr2 or HgI2. Single‐crystal X‐ray diffraction shows that both complexes are mononuclear structures, in which the bmi ligands coordinate to the HgII ions in monodentate modes. In the solid state, both complexes display three‐dimensional networks formed by a combination of hydrogen bonds and π–π interactions. The IR spectra and PXRD patterns of both complexes have also been recorded. 相似文献
7.
M. D. Crozet P. Vanelle M. Giorgi A. Gellis 《Acta Crystallographica. Section C, Structural Chemistry》2002,58(8):o496-o498
The title compounds, C13H15N3O5S and C11H10N2O4S2, respectively, both contain a phenylsulfonyl group connected, through a methylene bridge, to either a substituted nitroimidazole or nitro‐1,3‐thiazole ring. In the imidazole‐containing molecule, the nitro and sulfonyl groups are trans relative to the sulfonyl–methyl bond, while in the thiazole‐containing molecule, these substituents are cis. The stabilizing interactions within the crystals are also different between the two compounds. 相似文献
8.
Viktor Kettmann Jan Svtlík Jií Kubita 《Acta Crystallographica. Section C, Structural Chemistry》2004,60(6):o431-o433
In the title compound, C16H18N6O, an N‐carbonylimidazole derivative of pyrazoline‐1‐carboximidamide, the π‐electron density of the N atom in the 1‐position on the pyrazoline ring is delocalized through the amidine moiety and the adjacent carbonyl group. The imidazole ring, though coplanar with the rest of the molecule, is deconjugated. The pyrazoline ring adopts a flat‐envelope conformation, having the substituted phenyl ring oriented perpendicular to the mean plane of the heterocycle. Both of the two potential hydrogen‐bond donors are involved in intramolecular hydrogen‐bonding interactions. 相似文献
9.
Lei Guo Jia‐Qun Li Yu‐Ting Xie Chu‐Qin Lu Jian‐Zhong Wu 《Acta Crystallographica. Section C, Structural Chemistry》2014,70(5):428-431
In the coordination polymer catena‐poly[[[diaqua[5‐carboxy‐2‐(pyridin‐3‐yl)‐1H‐imidazole‐4‐carboxylato‐κ2N3,O4]lead(II)]‐μ‐5‐carboxy‐2‐(pyridin‐3‐yl)‐1H‐imidazole‐4‐carboxylato‐κ3N3,O4:N2] dihydrate], {[Pb(C10H6N3O4)(H2O)2]·2H2O}n, the two 5‐carboxy‐2‐(pyridin‐3‐yl)‐1H‐imidazole‐4‐carboxylate ligands have different coordination modes, one being terminal and the other bridging. The bridging ligand links PbII cations into one‐dimensional coordination polymer chains. The structure is also stabilized by intra‐ and interchain π–π stacking interactions between the pyridine rings, resulting in the formation of a two‐dimensional network. Extensive hydrogen‐bonding interactions lead to the formation of a three‐dimensional supramolecular network. 相似文献
10.
Christopher P. Walczak Matthew M. Yonkey Philip J. Squattrito Dillip K. Mohanty Kristin Kirschbaum 《Acta Crystallographica. Section C, Structural Chemistry》2008,64(5):o248-o251
1,3‐Bis(ethylamino)‐2‐nitrobenzene, C10H15N3O2, (I), and 1,3‐bis(n‐octylamino)‐2‐nitrobenzene, C22H39N3O2, (II), are the first structurally characterized 1,3‐bis(n‐alkylamino)‐2‐nitrobenzenes. Both molecules are bisected though the nitro N atom and the 2‐C and 5‐C atoms of the ring by twofold rotation axes. Both display intramolecular N—H...O hydrogen bonds between the amine and nitro groups, but no intermolecular hydrogen bonding. The nearly planar molecules pack into flat layers ca 3.4 Å apart that interact by hydrophobic interactions involving the n‐alkyl groups rather than by π–π interactions between the rings. The intra‐ and intermolecular interactions in these molecules are of interest in understanding the physical properties of polymers made from them. Upon heating in the presence of anhydrous potassium carbonate in dimethylacetamide, (I) and (II) cyclize with formal loss of hydrogen peroxide to form substituted benzimidazoles. Thus, 4‐ethylamino‐2‐methyl‐1H‐benzimidazole, C10H13N3, (III), was obtained from (I) under these reaction conditions. Compound (III) contains two independent molecules with no imposed internal symmetry. The molecules are linked into chains via N—H...N hydrogen bonds involving the imidazole rings, while the ethylamino groups do not participate in any hydrogen bonding. This is the first reported structure of a benzimidazole derivative with 4‐amino and 2‐alkyl substituents. 相似文献
11.
Wayland E. Noland Kevin P. Cole Doyle Britton 《Acta Crystallographica. Section C, Structural Chemistry》2003,59(5):o263-o267
The title (1H‐pyrrol‐2‐yl)pyridines, C9H8N2, substituted at the ortho, meta, and para positions of the pyridine ring all have hydrogen‐bonded arrangements with geometrically similar, nearly linear, N(pyrrole)—H⋯N(pyridine) hydrogen bonds of average length. The graph sets for the ortho, meta, and three para polymorphs are R(10), C(6), C(7), C(7), and R(28), respectively. 相似文献
12.
Pawe Wagner Krzysztof
wierczek Maciej Kubicki 《Acta Crystallographica. Section C, Structural Chemistry》2007,63(8):o445-o447
Infinite chains connected by N—H...N hydrogen bonding form the primary packing motif in two closely related 4‐nitroimidazole derivatives, viz. 5‐bromo‐2‐methyl‐4‐nitro‐1H‐imidazole, C4H4BrN3O2, (I), and 2‐methyl‐4‐nitro‐1H‐imidazole‐5‐carbonitrile, C5H4N4O2, (II). These chains are almost identical, even though in (II) there are two symmetry‐independent molecules in the asymmetric unit. The differences appear in the interactions between the chains; in (I), there are strong C—Br...O halogen bonds, which connect the chains into a two‐dimensional grid, while in (II), the cyano group does not participate in specific interactions and the chains are only loosely connected into a three‐dimensional structure. 相似文献
13.
Grzegorz Mlostoń Katarzyna Urbaniak Anthony Linden Heinz Heimgartner 《Helvetica chimica acta》2012,95(4):577-585
The attempted ethenylation at C(2) of 2‐unsubstituted 1H‐imidazole N‐oxides with ethyl acrylate (=prop‐2‐enoate) in the presence of Pd(OAc)2 does not occur. In contrast to the other aromatic N‐oxides, the [2+3] cycloaddition of imidazole N‐oxides predominates, and 3‐hydroxyacrylates, isomeric with the cycloadducts, are key products for the subsequent reaction. The final products were identified as dehydrated 2+1 adducts of 1H‐imidazole N‐oxide and ethyl acrylate. The role of the catalyst is limited to the dehydration of the intermediate 3‐hydroxypropanoates to give 1H‐imidazol‐2‐yl‐substituted acrylates. 相似文献
14.
Daniel E. Vicentes Ricaurte Rodríguez Justo Cobo Christopher Glidewell 《Acta Crystallographica. Section C, Structural Chemistry》2013,69(7):770-773
The molecules of 3‐amino‐4‐anilino‐1H‐isochromen‐1‐one, C15H12N2O2, (I), and 3‐amino‐4‐[methyl(phenyl)amino]‐1H‐isochromen‐1‐one, C16H14N2O2, (II), adopt very similar conformations, with the substituted amino group PhNR, where R = H in (I) and R = Me in (II), almost orthogonal to the adjacent heterocyclic ring. The molecules of (I) are linked into cyclic centrosymmetric dimers by pairs of N—H...O hydrogen bonds, while those of (II) are linked into complex sheets by a combination of one three‐centre N—H...(O)2 hydrogen bond, one two‐centre C—H...O hydrogen bond and two C—H...π(arene) hydrogen bonds. 相似文献
15.
《Acta Crystallographica. Section C, Structural Chemistry》2018,74(8):967-973
Crystals of poly[[aqua[μ3‐4‐carboxy‐1‐(4‐carboxylatobenzyl)‐2‐propyl‐1H‐imidazole‐5‐carboxylato‐κ5O1O1′:N3,O4:O5][μ4‐1‐(4‐carboxylatobenzyl)‐2‐propyl‐1H‐imidazole‐4‐carboxylato‐κ7N3,O4:O4,O4′:O1,O1′:O1]cadmium(II)] monohydrate], {[Cd2(C15H14N2O4)(C16H14N2O6)(H2O)]·H2O}n or {[Cd2(Hcpimda)(cpima)(H2O)]·H2O}n, (I), were obtained from 1‐(4‐carboxybenzyl)‐2‐propyl‐1H‐imidazole‐4,5‐dicarboxylic acid (H3cpimda) and cadmium(II) chloride under hydrothermal conditions. The structure indicates that in‐situ decarboxylation of H3cpimda occurred during the synthesis process. The asymmetric unit consists of two Cd2+ centres, one 4‐carboxy‐1‐(4‐carboxylatobenzyl)‐2‐propyl‐1H‐imidazole‐5‐carboxylate (Hcpimda2−) anion, one 1‐(4‐carboxylatobenzyl)‐2‐propyl‐1H‐imidazole‐4‐carboxylate (cpima2−) anion, one coordinated water molecule and one lattice water molecule. One Cd2+ centre, i.e. Cd1, is hexacoordinated and displays a slightly distorted octahedral CdN2O4 geometry. The other Cd centre, i.e. Cd2, is coordinated by seven O atoms originating from one Hcpimda2− ligand and three cpima2− ligands. This Cd2+ centre can be described as having a distorted capped octahedral coordination geometry. Two carboxylate groups of the benzoate moieties of two cpima2− ligands bridge between Cd2 centres to generate [Cd2O2] units, which are further linked by two cpima2− ligands to produce one‐dimensional (1D) infinite chains based around large 26‐membered rings. Meanwhile, adjacent Cd1 centres are linked by Hcpimda2− ligands to generate 1D zigzag chains. The two types of chains are linked through a μ2‐η2 bidentate bridging mode from an O atom of an imidazole carboxylate unit of cpima2− to give a two‐dimensional (2D) coordination polymer. The simplified 2D net structure can be described as a 3,6‐coordinated net which has a (43)2(46.66.83) topology. Furthermore, the FT–IR spectroscopic properties, photoluminescence properties, powder X‐ray diffraction (PXRD) pattern and thermogravimetric behaviour of the polymer have been investigated. 相似文献
16.
Viktor Kettmann Jan Lokaj Viktor Milata Jozef Salo Mohamed Mahmoud Mohamed Hasan 《Acta Crystallographica. Section C, Structural Chemistry》2002,58(6):o365-o366
The title compound, C11H10N3+·Cl?·H2O, belongs to the N1‐methyl‐substituted imidazo[4,5‐f]quinoline family, in which the heterocyclic ring is protonated at the pyridine rather than at the imidazole N atom. The molecule as a whole is almost exactly planar. The molecular structure has been compared with that of the 2‐amino analogue described in the literature, and it was found that the extra amino group of the latter is involved in conjugation with the adjacent double bond, i.e. the conjugation does not extend over the entire heterocyclic system. The cation of the title compound forms a strong hydrogen bond with the Cl? anion and the anions are interconnected by the water solvent molecule. 相似文献
17.
The reaction of 1H‐imidazole‐4‐carbohydrazides 1 , which are conveniently accessible by treatment of the corresponding esters with NH2NH2?H2O, with isothiocyanates in refluxing EtOH led to thiosemicarbazides (=hydrazinecarbothioamides) 4 in high yields (Scheme 2). Whereas 4 in boiling aqueous NaOH yielded 2,4‐dihydro‐3H‐1,2,4‐triazole‐3‐thiones 5 , the reaction in concentrated H2SO4 at room temperature gave 1,3,4‐thiadiazol‐2‐amines 6 . Similarly, the reaction of 1 with butyl isocyanate led to semicarbazides 7 , which, under basic conditions, undergo cyclization to give 2,4‐dihydro‐3H‐1,2,4‐triazol‐3‐ones 8 (Scheme 3). Treatment of 1 with Ac2O yielded the diacylhydrazine derivatives 9 exclusively, and the alternative isomerization of 1 to imidazol‐2‐ones was not observed (Scheme 4). It is important to note that, in all these transformations, the imidazole N‐oxide residue is retained. Furthermore, it was shown that imidazole N‐oxides bearing a 1,2,4‐triazole‐3‐thione or 1,3,4‐thiadiazol‐2‐amine moiety undergo the S‐transfer reaction to give bis‐heterocyclic 1H‐imidazole‐2‐thiones 11 by treatment with 2,2,4,4‐tetramethylcyclobutane‐1,3‐dithione (Scheme 5). 相似文献
18.
Eberhardt Herdtweck Alexander Zeller Thomas Strassner 《Acta Crystallographica. Section C, Structural Chemistry》2012,68(6):m166-m168
In the crystal structure of the title compound, [CoCl2(C7H12N2)2], molecular units are formed by coordination of the unsubstituted N atoms of two tert‐butyl‐substituted imidazole molecules and two chloride ligands, which distinguishes the complex from structures of imidazolium‐based dications with tetrachloridocobaltate dianions. There are two crystallographically independent molecules in the asymmetric unit, related by a noncrystallographic inversion centre. 相似文献
19.
Yun‐Bo Jiang Hui‐Zhong Kou Fei Gao Ru‐Ji Wang 《Acta Crystallographica. Section C, Structural Chemistry》2004,60(6):m261-m262
Using 2‐aminomethyl‐1H‐benzimidazole as the ligand, a new thiocyanate‐bridged copper(II) complex, namely bis(2‐aminomethyl‐1H‐benzimidazole‐κ2N2,N3)dithiocyanatocopper(II),[Cu(NCS)2(C8H9N3)], has been synthesized and structurally characterized. The Cu atom is five‐coordinated and exhibits a distorted square‐pyramidal geometry. The thiocyanate ions (NCS−) act as either bridging or terminal ligands. The bridging NCS− ligands connect neighboring Cu atoms, constructing chains, while the terminal NCS− ligands form hydrogen bonds with amine H atoms, leading to a complicated network. 相似文献
20.
Heng Zhang Liangliang Chang Na Wang Xiaopeng Xuan 《Acta Crystallographica. Section C, Structural Chemistry》2013,69(10):1173-1176
The title compound, C6H9N2O2+·Cl−·C6H8N2O2·H2O, contains one 2‐(3‐methyl‐1H‐imidazol‐3‐ium‐1‐yl)acetate inner salt molecule, one 1‐carboxymethyl‐3‐methyl‐1H‐imidazol‐3‐ium cation, one chloride ion and one water molecule. In the extended structure, chloride anions and water molecules are linked via O—H...Cl hydrogen bonds, forming an infinite one‐dimensional chain. The chloride anions are also linked by two weak C—H...Cl interactions to neighbouring methylene groups and imidazole rings. Two imidazolium moieties form a homoconjugated cation through a strong and asymmetric O—H...O hydrogen bond of 2.472 (2) Å. The IR spectrum shows a continuous D‐type absorption in the region below 1300 cm−1 and is different to that of 1‐carboxymethyl‐3‐methylimidazolium chloride [Xuan, Wang & Xue (2012). Spectrochim. Acta Part A, 96 , 436–443]. 相似文献