1‐Benzoyl‐3‐[(2‐benzylsulfanyl)phenyl]thiourea

In the title compound, C₂₁H₁₈N₂OS₂, a strong intramolecular N—H...O hydrogen bond [N...O = 2.642 (3) Å] between the amide N atom and the benzoyl O atom forms an almost planar six‐membered ring in the central part of the molecule. In the crystal, molecules are packed through weak N—H...S interactions. Intra‐ and intermolecular hydrogen bonds and van der Waals interactions are the stabilizing forces for the crystal structure.     

Crystal Structure and Ethylene Oligomerization Catalytic Activity of {2-Carbethoxy-6-[1-[（2,6-diethylphenyl）imino]ethyl]pyridine}CoCl2

The unsymmetric precursor ethyl 6-acetylpyridine-2-carboxylate （4） was synthesized from 2,6-dimethylpyridine （1）. On the basis of this precursor, a new mono（imino）pyridine ligand （5） and the corresponding Co（Ⅱ） complex {2-carbethoxy-6-[1-[（2,6-diethylphenyl）imino]ethyl]pyridine}CoCl2 （6） were prepared. The crystal structure of complex indicates that the 2-carbethoxy-6-iminopyridine is coordinated to the cobalt as a tridentate ligand using [N, N, O] atoms, and the coordination geometry of the central cobalt is a distorted trigonal bipyramid, with the pyridyl nitrogen atom and the two chlorine atoms forming the equatorial plane. Being applied to the ethylene oligomedzation, this cobalt complex shows catalytic activity of 1.820× 10^4 g/mol-Cooh at 101325 Pa of ethylene at 15.5℃ for 1 h, when 1000 equiv, of methylaluminoxane （MAO） is employed as the cocatalyst.     

(R)‐N‐[(R)‐1‐(2‐Hydroxy‐5‐methyl­phenyl)‐2‐phenyl­ethyl]‐2‐methyl‐1‐phenyl­propyl­ammonium chloride

In the title compound, C₂₅H₃₀NO⁺·Cl⁻, the mol­ecules are linked by a combination of inter­molecular N—H⋯Cl and O—H⋯Cl hydrogen bonds and intra­molecular N—H⋯O hydrogen bonds. The absolute configuration of the new stereogenic centre (the C atom adjacent to the N atom on the phenol side) is determined to have an R configuration.     

Novel 5‐Methyl‐2‐[(un)substituted phenyl]‐4‐{4,5‐dihydro‐ 3‐[(un)substituted phenyl]‐5‐(1,2,3,4‐tetrahydroisoquinoline‐2‐yl)pyrazol‐1‐yl}‐oxazole Derivatives: Synthesis and Anticancer Activity

Eleven novel 5‐methyl‐2‐[(un)substituted phenyl]‐4‐{4,5‐dihydro‐3‐[(un)substituted phenyl]‐5‐(1,2,3,4‐tetrahydroisoquinoline‐2‐yl)pyrazol‐1‐yl}‐oxazole derivatives were synthesized and characterized by elemental analysis, ESI‐MS, ¹H NMR and ¹³C NMR. All of the compounds have been screened for their antiproliferative activities against PC‐3 cell (human prostate cancer) and A431 cell (human epidermoid carcinoma cancer) lines in vitro. The results revealed that compounds 4g , 4j and 4k exhibited the strong inhibitory activities against the PC‐3 cell lines (with IC₅₀ values of 2.8±0.11, 3.1±0.10 and 3.0±0.06 μg/mL, respectively).     

rac‐1‐[(2‐Methoxyethyl)sulfanyl]‐2‐[(2‐methoxyethyl)sulfinyl]benzene and its PdCl2 complex

As an extension of recent findings on the recovery of palladium with dithioether extractants, single crystals of the chelating vicinal thioether sulfoxide ligand rac‐1‐[(2‐methoxyethyl)sulfanyl]‐2‐[(2‐methoxyethyl)sulfinyl]benzene, C₁₂H₁₈O₃S₂, (I), and its square‐planar dichloridopalladium complex, rac‐dichlorido{1‐[(2‐methoxyethyl)sulfanyl]‐2‐[(2‐methoxyethyl)sulfinyl]benzene‐κ²S,S′}palladium(II), [PdCl₂(C₁₂H₁₈O₃S₂)], (II), have been synthesized and their structures analysed. The molecular structure of (II) is the first ever characterized involving a dihalogenide–Pd^II complex in which the palladium is bonded to both a thioether and a sulfoxide functional group. The structural and stereochemical characteristics of the ligand are compared with those of the analogous dithioether compound [Traeger et al. (2012). Eur. J. Inorg. Chem. pp. 2341–2352]. The sulfinyl O atom suppresses the electron‐pushing and mesomeric effect of the S—C...;C—S unit in ligand (I), resulting in bond lengths significantly different than in the dithioether reference compound. In contrast, in complex (II), those bond lengths are nearly the same as in the analogous dithioether complex. As observed previously, there is an interaction between the central Pd^II atom and the O atom that is situated above the plane.     

Synthesis and characterization of some novel 2‐{2‐[1‐(3‐substituted‐phenyl)‐1H‐1,2,3‐triazol‐4‐yl‐] ethyl}‐1‐substituted‐1H‐benzo [d] imidazole derivatives

Synthesis of some novel 2‐{2‐[1‐(3‐substitutedphenyl)‐1H‐1,2, 3‐triazol‐4‐yl‐]ethyl)‐1H‐benzo[d]‐imidazole derivatives, by the condensation of o‐phenylenediamine with 3‐(1‐(3‐substituted‐phenyl)‐1H‐1,2,3‐triazol‐4‐yl) propanoic acid and then subsequent reactions with different substituted alkyl halides as electrophiles are mentioned. The synthesized compounds were characterized by ¹H NMR, EI‐MS and IR spectroscopic techniques.     

(3R,4S)‐3‐Phenyl‐1‐[(R)‐1‐phenyl­ethyl]‐4‐[(R)‐1‐phenylethyliminomethyl]azetidin‐2‐one

The configuration of the chiral ring atoms of the title compound, C₂₆H₂₆N₂O, obtained in an enantioselective synthesis, has been established relative to the known R configuration of the α‐methyl­benzyl moieties. The crystal packing involves a two‐dimensional network of C—H?π interactions between the aromatic rings.     

2‐Hydro­xy‐5‐[(E)‐(4‐methoxy­phenyl)­diazenyl]­benzoic acid

The title compound, C₁₄H₁₂N₂O₄, shows an E conformation about the diazenyl N atoms. The crystal structure features layers of mol­ecules with the primary connection between the layers afforded by carboxyl­ic acid dimer motifs; no evidence for extensive π–π stacking between the layers was found.     

Synthesis,structure and cytotoxicity of new 2‐[(3‐aminopropyl)dimethylsilyl]‐5‐furfural diethylacetals and 2‐[(3‐aminopropyl)dimethylsilyl]‐5‐phenylfurans

Novel 2‐[(3‐aminopropyl)dimethylsilyl]‐5‐furfural diethylacetals and 2‐[(3‐aminopropyl)di‐methylsilyl]‐5‐phenylfurans have been synthesized by a hydrosilylation reaction of aliphatic and heterocyclic N‐allylamines in the presence of the Speier's catalyst. The effects of the structure of the amine and nature of organic substituent at the furan ring on the cytotoxicity of the new compounds have been studied. Copyright © 2013 John Wiley & Sons, Ltd.     

Synthesis and single crystal X‐ray determination of the Schiff base 1‐[(2‐isopropyl‐5‐methylphenoxy)hydrazono] ethyl ferrocene

The reaction of acetylferrocene [Fe(η‐C₅H₅)(η‐C₅H₄COCH₃)] (1) with (2‐isopropyl‐5‐methylphenoxy) acetic acid hydrazide [CH₃C₆H₃CH(CH₃)₂OCH₂CONHNH₂] (2) in refluxing ethanol gives the stable light‐orange–brown Schiff base 1‐[(2‐isopropyl‐5‐methylphenoxy)hydrazono] ethyl ferrocene, [CH₃C₆H₃CH(CH₃)₂OCH₂CONHN?C(CH₃)Fe(η‐C₅H₅)(η‐C₅H₄)] (3). Complex 3 has been characterized by elemental analysis, IR, ¹H NMR and single crystal X‐ray diffraction study. It crystallizes in the monoclinic space group P2₁/n, with a = 9.6965(15), b = 7.4991(12), c = 29.698(7) Å, β = 99.010(13) °, V = 2132.8(7) ų, D_calc = 1.346 Mg m^?3; absorption coefficient, 0.729 mm^?1. The crystal structure clearly shows the characteristic [N? H···O] hydrogen bonding between the two adjacent molecules of 3. This acts as a bidentale ligand, which, on treatment with [Ru(CO)₂Cl₂] _n, gives a stable bimetallic yellow–orange complex (4). Copyright © 2002 John Wiley & Sons, Ltd.     

2‐[(1‐Imidazolyl)formyloxy]ethyl methacrylate as a new chemical precursor of functional polymers

A novel activated derivative of methacrylic acid, namely 2‐[(1‐imidazolyl)formyloxy]ethyl methacrylate was synthesized and homopolymerized. The resulting polymer was used in exchange reactions with alcohols and amines, thus showing a potential for the synthesis of multifunctional polymers. All reactions, expecially those carried out in the presence of amines, proceeded under mild conditions. 2‐[(1‐Imidazolyl)formyloxy]ethyl methacrylate can also be regarded as a valuable precursor for the preparation of new and easily polymerizable functional monomers.     

Synthesis of 1‐[(1R)‐1‐(6‐fluoro‐1,3‐benzothiazol‐2‐yl)ethyl]‐3‐substituted phenyl ureas and their inhibition activity to acetylcholinesterase and butyrylcholinesterase

A series of novel 1‐[(1R)‐1‐(6‐fluoro‐1,3‐benzothiazol‐2‐yl)ethyl]‐3‐substituted phenyl ureas were synthesized by the condensation of (1R)‐1‐(6‐fluoro‐1,3‐benzothiazol‐2‐yl)ethanamine with substituted phenyl isocyanates under mild conditions. Their structures were confirmed ¹H, ¹³C, and ¹⁹F NMR spectra, and elemental analyses. The optical activities were confirmed by optical rotation measurements. The inhibition activity of 1‐[(1R)‐1‐(6‐fluoro‐1,3‐benzothiazol‐2‐yl)ethyl]‐3‐substituted phenyl ureas to acetylcholinesterase (ACHE) and butyrylcholinesterase (BCHE) was also tested. Preliminary bioassay indicated that the target ureas displayed excellent acetylcholinesterase and butyrylcholinesterase inhibition activity. J. Heterocyclic Chem., 2011.     

Synthesis and spectral properties of 2‐[(o‐ and p‐substituted)aminophenyl] ‐3H‐5‐[(o‐ and p‐substituted)phenyl]‐7‐chloro‐1,4‐benzodiazepines

A series of twelve new 2‐[(o‐ and p‐substituted)aminophenyl]‐3H‐5‐[(o‐ and p‐substituted)phenyl]‐7‐chloro‐1,4‐benzodiazepines, which have possible pharmacological properties has been obtained. The synthesis was carried out following six steps. The structure of all products was corroborated by ir, ¹H nmr, ¹³C nmr and ms. In addition for the compound 2‐(o‐chloroaminophenyl)‐3H‐5‐(o‐fluorophenyl)‐7‐chloro‐1,4‐benzodiazepine 7, its structure was confirmed by X‐ray diffraction.     

Synthesis and spectral properties of 7‐chloro‐5‐[(o‐ and p‐R1)phenyl]‐1‐R2‐3H‐[1,4]benzodiazepin‐2‐ones

A series of twelve new 7‐chloro‐5‐[(o‐ and p‐R₁)phenyl]‐1‐R₂‐3H‐[1,4] benzo‐diazepin‐2‐ones, which have possible pharmacological properties were synthesized. The synthesis of all the final compounds was carried out by four steps. The structure of all final products was corroborated by ir, ¹H nmr, ¹³C nmr and ms, and have been obtained in 35‐94% yield.     

Ethyl 2‐methoxy‐6‐[(triphenylphosphoranylidene)amino]nicotinate and ethyl 2‐methylsulfanyl‐6‐[(triphenylphosphoranylidene)amino]nicotinate

The molecules of ethyl 2‐methoxy‐6‐[(triphenylphosphoranylidene)amino]nicotinate, C₂₇H₂₅N₂O₃P, (I), and ethyl 2‐methylsulfanyl‐6‐[(triphenylphosphoranylidene)amino]nicotinate, C₂₇H₂₅N₂O₂PS, (II), have almost identical bond lengths and molecular conformations, and both show evidence for polarized electronic structures. However, the crystal structures, as illustrated by the weak hydrogen bonds linking the molecules, are significantly different. The significance of this study lies in the observation that two compounds which are almost identical in constitution, configuration and conformation nonetheless adopt different crystal structures.     

(E)‐2‐[(4‐Chlorophenyl)iminomethyl]‐5‐methoxyphenol and (E)‐2‐[(2‐chlorophenyl)iminomethyl]‐5‐methoxyphenol: X‐ray and DFT‐calculated structures

The crystal structures of the title 4‐chlorophenyl, (I), and 2‐chlorophenyl, (II), compounds, both C₁₄H₁₂ClNO₂, have been determined using X‐ray diffraction techniques and the molecular structures have also been optimized at the B3LYP/6‐31 G(d,p) level using density functional theory (DFT). The X‐ray study shows that the title compounds both have strong intramolecular O—H...N hydrogen bonds and that the crystal networks are primarily determined by weak C—H...π and van der Waals interactions. The strong intramolecular O—H...N hydrogen bond is evidence of the preference for the phenol–imine tautomeric form in the solid state. The IR spectra of the compounds were recorded experimentally and also calculated for comparison. The results from both the experiment and theoretical calculations are compared in this study.     

Synthesis and spectral properties of 2‐methylthio‐3H‐7‐[(o‐; m‐ and p‐substituted)phenoxy]‐4‐(p‐substituted‐phenyl)‐[1,5]benzodiazepines

A series of eleven new 2‐methylthio‐3H‐7‐[(o‐; m‐ and p‐substituted) phenoxy]‐4‐(p‐substituted‐phenyl)‐[1,5]benzodiazepines, which have potentially useful pharmacological activities, has been synthesized by condensing the 4‐[(o‐; m‐ and p‐R₁)phenoxy]‐1,2‐phenylendiamines with 3,3‐dimercapto‐1‐(p‐R₂‐phenyl)‐2‐propen‐1‐one. Afterward the lH‐[1,5]benzodiazepine‐2‐thiones obtained were treated with sodium hydride and methyl iodide. The structure of all products was corroborated by ir, ¹H nmr, ¹³C nmr and ms.     

Synthesis and spectral determination of new derivatives of 1‐[(p‐substituted)phenyl]‐3a‐[(o‐ and p‐substituted)phenyl]‐5‐chloro‐9‐methylthio‐10,3a‐dihydro‐[1,2,4]‐oxadiazolo[2,3‐b][1,4]benzodiazepines

A new synthesis to obtain eight novel derivatives of 1‐[(p‐substituted)phenyl]‐3a‐[(o‐ and p‐substituted)‐phenyl]‐5‐chloro‐9‐methylthio‐10,3a‐dihydro‐[1,2,4]‐oxadiazolo[2,3‐b][1,4]benzodiazepines with possible biological and pharmacological activity as anxiolytics, hypnotics, anticonvulsants in the central nervous system. The final products were obtained by condensation between 2‐methylthio‐5‐[(o‐; p‐substituted)‐phenyl]‐3H‐7‐chloro‐[1,4]benzodiazepine with benzonitrile oxide generated in situ from benzohydroxamoyl chloride in triethylamine. The structure of all products was corroborated by ir, ¹H‐nmr, ¹³C‐nmr, with experiments bidimensional and ms in low and high resolution.     

2‐Meth­oxy‐4‐[(5‐oxo‐2‐phenyl‐4,5‐dihydro‐1,3‐oxazol‐4‐yl­idene)meth­yl]­phenyl 4‐methyl­benzene­sulfonate

Mol­ecules of the title compound, C₂₄H₁₉NO₆S, adopt the Z configuration and have a distorted tetra­hedral geometry around the S atom. The oxazolone, 2‐phenyl and methoxy­phenyl rings are approximately coplanar. The C atom between the methoxy­phenyl and oxazolone rings displays a distorted trigonal bonding geometry. Pairs of mol­ecules are linked into dimers through weak C—H⋯O hydrogen bonds.