Open AccessShort Note
4-Phenethylthio-2-phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H)-one
Molbank 2017, 2017(4), M970; doi:10.3390/M970 (registering DOI) -
Abstract
Exploring the pharmacologically important pyrazolo[1,5-a][1,3,5]triazin-7(6H)-one scaffold for the construction of new bioactive compounds, we developed a synthesis of 4-phenethylthio-2-phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H)-one (4) via S-alkylation of 2-phenyl-4-thioxopyrazolo[1,5-a][1,3,5]triazine-7(6H)-one (3), prepared
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Exploring the pharmacologically important pyrazolo[1,5-a][1,3,5]triazin-7(6H)-one scaffold for the construction of new bioactive compounds, we developed a synthesis of 4-phenethylthio-2-phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H)-one (4) via S-alkylation of 2-phenyl-4-thioxopyrazolo[1,5-a][1,3,5]triazine-7(6H)-one (3), prepared by the double ring closure of pyrazole and triazine rings upon the treatment of 1-cyanoacetyl-4-benzoylthiosemicarbazide (2) with alkali. The antiproliferative activity of 4 against human lung cancer (A549) and human breast cancer (MDA-MB231) cell lines was investigated. Compound 4 was found to be more active against lung cancer cells than breast cancer cells. Full article
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Open AccessCommunication
A Novel PCC-Catalyzed Process Involving the Oxidative Cleavage of an α-Bromomethyl-tetrahydrofuran Bond. Synthesis of (2S,3R)-2-{(R)-Bromo[(2R,3R,5S,6R)-3,5-dibromo-6-ethyltetrahydro-2H-pyran-2-yl]methyl}-5-oxotetrahydrofuran-3-yl Benzoate
Molbank 2017, 2017(4), M969; doi:10.3390/M969 -
Abstract
In this note, we report the discovery of a novel pyridinium chlorochroamte-catalyzed process in which an α-bromomethyl-tetrahydrofuran bond was oxidatively cleaved to give a γ-lactone functionality. The title compound was synthesized from a C15 polybrominated acetogenin compound, isolated from the marine sponge Mycale
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In this note, we report the discovery of a novel pyridinium chlorochroamte-catalyzed process in which an α-bromomethyl-tetrahydrofuran bond was oxidatively cleaved to give a γ-lactone functionality. The title compound was synthesized from a C15 polybrominated acetogenin compound, isolated from the marine sponge Mycale rotalis, by benzoylation followed by pyridinium chlorochromate-catalyzed oxidation. This new degraded derivative was fully characterized by 1H-NMR, 13C-NMR, FTIR (Fourier transform infrared), EIMS (Electron impact mass spectrometry) and HRESIMS (High-resolution electrospray ionisation mass spectrometry). Full article
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Open AccessShort Note
1,3-Bis(1,2,4-triazol-1-yl)adamantane
Molbank 2017, 2017(4), M968; doi:10.3390/M968 -
Abstract
Functional adamantane derivatives are interesting as active pharmaceutical ingredients, building blocks for supramolecular ensembles, and ligands in light of the coordination chemistry of functional materials. In this communication, synthesis of two isomeric 1,3-bis(1,2,4-triazolyl)adamantanes by the reaction of 1,3-dibromoadamantane with 1,2,4-triazole in the absence
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Functional adamantane derivatives are interesting as active pharmaceutical ingredients, building blocks for supramolecular ensembles, and ligands in light of the coordination chemistry of functional materials. In this communication, synthesis of two isomeric 1,3-bis(1,2,4-triazolyl)adamantanes by the reaction of 1,3-dibromoadamantane with 1,2,4-triazole in the absence of solvent is reported. The products, namely 1,3-bis(1,2,4-triazol-1-yl)adamantane and 1-(1,2,4-triazol-1-yl)-3-(1,2,4-triazol-4-yl)adamantane were separated by column chromatography and identified by NMR and mass-spectrometry. Full article
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Open AccessFeature PaperShort Note
N1-(5-Fluoro-2,4-dinitrophenyl)-N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine
Molbank 2017, 2017(4), M967; doi:10.3390/M967 -
Abstract
Treating 1,5-difluoro-2,4-dinitrobenzene (1) with N1-phenyl-5-(trifluoromethyl)benzene-1,2-diamine (4) and N,N-diisopropylethylamine in EtOH at ca. 0 °C for 4 h affords a mixture of N1-(5-ethoxy-2,4-dinitrophenyl)-N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine (5) (38%) and N
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Treating 1,5-difluoro-2,4-dinitrobenzene (1) with N1-phenyl-5-(trifluoromethyl)benzene-1,2-diamine (4) and N,N-diisopropylethylamine in EtOH at ca. 0 °C for 4 h affords a mixture of N1-(5-ethoxy-2,4-dinitrophenyl)-N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine (5) (38%) and N1-(5-fluoro-2,4-dinitrophenyl)-N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine (6) (51%) that can be separated by chromatography. Repeating the reaction in dichloromethane led to the sole formation of N1-(5-fluoro-2,4-dinitrophenyl)-N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine (6) in 96% yield. Full article
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Open AccessShort Note
(±)-Methyl 1,1a,2,7b-Tetrahydro-2-oxocyclopropa[c] Chromene-1a-carboxylate
Molbank 2017, 2017(4), M966; doi:10.3390/M966 -
Abstract
A novel method for the preparation of (±)-methyl 1,1a,2,7b-tetrahydro-2-oxocyclopropa[c]chromene-1a-carboxylate has been developed. The cyclopropanation of methyl coumarin-3-carboxylate provided title compound in moderate yield by dropwise treatment with 1.5 equiv. of dimethylsulfoxonium methylide over 6 h. The structure of the newly synthesized
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A novel method for the preparation of (±)-methyl 1,1a,2,7b-tetrahydro-2-oxocyclopropa[c]chromene-1a-carboxylate has been developed. The cyclopropanation of methyl coumarin-3-carboxylate provided title compound in moderate yield by dropwise treatment with 1.5 equiv. of dimethylsulfoxonium methylide over 6 h. The structure of the newly synthesized compound was determined using 1H-, 13C-NMR, IR and mass spectral data. Full article
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Open AccessCommunication
Heterobimetallic 3d-4f (Zn/La) {6,6′-Dimethoxy-2,2′-[naphthalene-2,3-diylbis(nitrilomethylidyne)]diphenolato}-pyridylzinc(II)-tris(nitrato-O,O′)lanthanum(III) Monohydrate
Molbank 2017, 2017(4), M965; doi:10.3390/M965 -
Abstract
Herein, we report the synthesis and structural characterization of a complex with extended aromaticity based on a naphthalene-bridged Schiff base complex with two metal binding pockets. In a first step, the Zn(II) complex (ZnL), {6,6′-dimethoxy-2,2′-[naphthalene-2,3-diylbis(nitrilomethylidyne)]diphenolato}a-pyridylzinc(II) was isolated followed by refluxing with lanthanum(III) nitrate
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Herein, we report the synthesis and structural characterization of a complex with extended aromaticity based on a naphthalene-bridged Schiff base complex with two metal binding pockets. In a first step, the Zn(II) complex (ZnL), {6,6′-dimethoxy-2,2′-[naphthalene-2,3-diylbis(nitrilomethylidyne)]diphenolato}a-pyridylzinc(II) was isolated followed by refluxing with lanthanum(III) nitrate to produce the heterobimetallic complex {ZnL[La(NO3)3·H2O]}. Crystals suitable for X-ray diffraction were grown by vapor diffusion of THF into a pyridine solution of the complex. The monoclinic unit cell (P21/n) is commensurately modulated along the c-axis direction and contains four crystallographically independent molecules with pseudo-translational symmetry being broken by slightly differing orientations of included pyridine and THF solvate molecules. The zinc atom adopts a distorted square pyramidal geometry and sits slightly above the ligand plane, whereas the lanthanum atom adopts an all-face capped trigonal prismatic geometry and sits below the ligand plane. Structural characterization of this diamagnetic complex lays the groundwork for applying these synthetic techniques to the near-infrared emitting lanthanides for practical application. Full article
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Open AccessCommunication
(S)-2-(4-Chlorobenzoyl)-1,2,3,4-tetrahydrobenzo[e]pyrazino[1,2-a][1,4]diazepine-6,12(11H,12aH)-dione—Synthesis and Crystallographic Studies
Molbank 2017, 2017(4), M964; doi:10.3390/M964 -
Abstract
(S)-2-(4-Chlorobenzoyl)-1,2,3,4-tetrahydrobenzo[e]pyrazino[1,2-a][1,4]diazepine-6,12(11H,12aH)-dione was obtained in a three-step, one-pot synthesis, starting from optically pure (S)-2-piperazine carboxylic acid dihydrochloride. Selective acylation of the β-nitrogen atom followed by condensation with isatoic anhydride and cyclization
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(S)-2-(4-Chlorobenzoyl)-1,2,3,4-tetrahydrobenzo[e]pyrazino[1,2-a][1,4]diazepine-6,12(11H,12aH)-dione was obtained in a three-step, one-pot synthesis, starting from optically pure (S)-2-piperazine carboxylic acid dihydrochloride. Selective acylation of the β-nitrogen atom followed by condensation with isatoic anhydride and cyclization with HATU/DIPEA to a seven-member benzodiazepine ring, led to the tricyclic benzodiazepine derivative. Crystallographic studies and initial biological screening were performed for the title compound. Full article
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Open AccessShort Note
N-{4-[(2E)-3-(2H-1,3-Benzodioxol-5-yl)prop-2-enoyl]phenyl}quinoline-3-carboxamide
Molbank 2017, 2017(4), M960; doi:10.3390/M960 -
Abstract
An amide chalconehas been synthesized in a two-step reaction. First, N-(4-acetylphenyl)quinoline-3-carboxamide 2 was synthesized by the reaction of quinoline-3-carboxylic acid 1 and thionyl chloride (SOCl2), following the addition of 4-aminoacetophenone. Then, a typical Claisen–Schmidtreactionwas made between 2 and piperonal using
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An amide chalconehas been synthesized in a two-step reaction. First, N-(4-acetylphenyl)quinoline-3-carboxamide 2 was synthesized by the reaction of quinoline-3-carboxylic acid 1 and thionyl chloride (SOCl2), following the addition of 4-aminoacetophenone. Then, a typical Claisen–Schmidtreactionwas made between 2 and piperonal using KOH solution as a catalystin ethanol, under ultrasonic irradiation. The structure of the target compound was established by FTIR (Fourier-transform infrared spectroscopy), HRMS, 1H and 13C-NMR. Full article
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Scheme 1

Open AccessShort Note
1,8-bis(2-hydroxy-3,5-di-tert-butylbenzyl)-4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane
Molbank 2017, 2017(4), M963; doi:10.3390/M963 -
Abstract
A cyclam (1,4,8,11-tetraazacyclotetradecane)-based macrocycle bearing two benzyl and two 2-hydroxy-3,5-di-tert-butylbenzyl pendent arms was synthesized and characterized using spectroscopic techniques and single crystal X-ray diffraction. The macrocycle crystallizes in the triclinic space group P-1, with the asymmetric unit containing one-half of
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A cyclam (1,4,8,11-tetraazacyclotetradecane)-based macrocycle bearing two benzyl and two 2-hydroxy-3,5-di-tert-butylbenzyl pendent arms was synthesized and characterized using spectroscopic techniques and single crystal X-ray diffraction. The macrocycle crystallizes in the triclinic space group P-1, with the asymmetric unit containing one-half of the molecule. The structure is stabilized by hydrogen-bonding which exists between the phenolic protons and the nitrogen atoms of the macrocyclic ring. The presence of this hydrogen bonding is observed in the 1H-NMR due to the deshielded nature of the phenolic OH peak (δ 9.99). Cyclic voltammetry of the ligand revealed a single quasi-reversible peak at −0.58 V (Epc = −0.48 V and Epa = −0.68 V), which is due to the electrochemical oxidation of the phenol to the phenoxyl radical. Full article
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Open AccessFeature PaperShort Note
1,3-Bis(2,6-diisopropylphenyl)-2-trichloromethylimidazolidine
Molbank 2017, 2017(4), M962; doi:10.3390/M962 -
Abstract
A new chloroform adduct of the N-heterocyclic carbene (NHC) 1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene (SIPr) has been prepared via C–H bond activation of the chloroform at the carbene carbon. This redox product was crystallized and was characterized by 1H and 13C-NMR spectroscopy, elemental analysis
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A new chloroform adduct of the N-heterocyclic carbene (NHC) 1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene (SIPr) has been prepared via C–H bond activation of the chloroform at the carbene carbon. This redox product was crystallized and was characterized by 1H and 13C-NMR spectroscopy, elemental analysis (EA), and single-crystal X-ray diffraction. The 1H and 13C-NMR spectroscopic data are in agreement with the crystal structure. Density functional theory (DFT) calculations were performed as a means for comparison to experimental data and the computational results are in agreement with those obtained experimentally. Full article
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Open AccessShort Note
5,9,11-Trihydroxy-10-(2″-hydroxy-3″-methylbut-3″-en-1-yl)-2,2-dimethyl-3-(2′-methylbut-3′-en-2′-yl)-2H,12H-pyrano[2,3-a]xanthen-12-one from Calophyllum pseudomole
Molbank 2017, 2017(4), M961; doi:10.3390/M961 -
Abstract
A new pyranocoumarin, namely 5,9,11-trihydroxy-10-(2″-hydroxy-3″-methylbut- 3″en-1-yl)-2,2-dimethyl-3-(2′-methylbut-3′-en-2′-yl)-2H,12H-pyrano[2,3-a]xanthen-12-one 1, was isolated from the stem barkof Calophyllum pesudomole. The structure of compound 1was elucidated based on its ultaraviolet (UV); infrared (IR); high resolution electro spray ionization mass spectrometry (HRESIMS);
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A new pyranocoumarin, namely 5,9,11-trihydroxy-10-(2″-hydroxy-3″-methylbut- 3″en-1-yl)-2,2-dimethyl-3-(2′-methylbut-3′-en-2′-yl)-2H,12H-pyrano[2,3-a]xanthen-12-one 1, was isolated from the stem barkof Calophyllum pesudomole. The structure of compound 1was elucidated based on its ultaraviolet (UV); infrared (IR); high resolution electro spray ionization mass spectrometry (HRESIMS); 1D and 2D nuclear magnetic resonance (NMR) spectral data. Full article
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Open AccessShort Note
(2-Deoxy-2-{[2-(2-pyridinyl-κN)-4-thiazolecarbonyl-κN3]amino}-α-d-glucopyranose)dichloropalladium(II) Methanol Solvate
Molbank 2017, 2017(4), M959; doi:10.3390/M959 -
Abstract
A novel palladium(II) complex with a glycoconjugated 2-(2-pyridyl)thiazole ligand was synthesized. Single-crystal X-ray analysis revealed a packing structure that may be stabilized by hydrogen bonding between sugar moieties and between methanol (crystal solvent) and a sugar moiety. Full article
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Open AccessShort Note
Methyl N-[1-(Benzoylamino)-2-methoxy-2-oxoethyl]-tryptophanate
Molbank 2017, 2017(4), M958; doi:10.3390/M958 -
Abstract
The title compound, methyl N-[1-(benzoylamino)-2-methoxy-2-oxoethyl]tryptophanate 2, was synthesized in high yield, via N-alkylation reaction of methyl 2-azido-2-benzamidoacetate with methyl 2-amino-3-(1H-indol-3-yl)propanoate in acetone, with the presence of diisopropylethylamine as a base. The structure of the prepared compound was characterized
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The title compound, methyl N-[1-(benzoylamino)-2-methoxy-2-oxoethyl]tryptophanate 2, was synthesized in high yield, via N-alkylation reaction of methyl 2-azido-2-benzamidoacetate with methyl 2-amino-3-(1H-indol-3-yl)propanoate in acetone, with the presence of diisopropylethylamine as a base. The structure of the prepared compound was characterized by 1H, 13C NMR in addition to MS, X-Ray diffraction data, and elemental analysis. This compound was tested in vitro for its antibacterial activity against Gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus, and Gram-negative bacteria, Escherichia coli,Pseudomonas aeruginosa, and Salmonella enteric. The MIC values showed that the synthesized compound had a bactericidal effect against the strains tested. Full article
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Open AccessShort Note
Crystal Structure of Bis(2,4,6-trimethylphenyl)-phosphine Oxide
Molbank 2017, 2017(3), M957; doi:10.3390/M957 -
Abstract
The single crystal structure of bis(2,4,6-trimethylphenyl)phosphine oxide has been determined. All interatomic distances and angles can be considered normal. The aryl substituents adopt an intermediate configuration when compared to both sterically unhindered (e.g., diphenylphosphine oxide) and congested (e.g., bis(2,4,6-tri-tert-butylphenyl)phosphine oxide) secondary
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The single crystal structure of bis(2,4,6-trimethylphenyl)phosphine oxide has been determined. All interatomic distances and angles can be considered normal. The aryl substituents adopt an intermediate configuration when compared to both sterically unhindered (e.g., diphenylphosphine oxide) and congested (e.g., bis(2,4,6-tri-tert-butylphenyl)phosphine oxide) secondary phosphine oxides, illustrating the influence of steric congestion on the molecular structure. Full article
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Figure 1

Open AccessShort Note
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 4-Aminobutyrate Hydrochloride
Molbank 2017, 2017(3), M956; doi:10.3390/M956 -
Abstract
The title ester (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-aminobutyrate hydrochloride was obtained in 96% yield via Steglich esterification. The structure of the target compound was established by FTIR, HR-MS, 1H-NMR, 13C-NMR spectral analysis, and single crystal X-ray diffraction study.
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The title ester (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-aminobutyrate hydrochloride was obtained in 96% yield via Steglich esterification. The structure of the target compound was established by FTIR, HR-MS, 1H-NMR, 13C-NMR spectral analysis, and single crystal X-ray diffraction study. Single crystals of the title ester suitable for X-ray investigation were obtained by slow evaporation of the methanolic solution at room temperature. The purity of compound was assessed using HPLC coupled to mass spectrometry. Full article
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Open AccessShort Note
(E)-3′,6′-bis(Diethylamine)-2-[(2-methoxynaphthalen-1-yl)methyleneamino]spiro[isoindoline-1,9′-xanthen]-3-one
Molbank 2017, 2017(3), M955; doi:10.3390/M955 -
Abstract
The title compound, (E)-3′,6′-bis(diethylamine)-2-[(2-methoxynaphthalen-1-yl)methyleneamino]spiro[isoindoline-1,9′-xanthen]-3-one, was synthesized in 92% isolated yield using microwave-assisted organic synthesis. This new rhodamine derivative was fully characterized by 1H-NMR, 13C-NMR, FTIR and high resolution MS. Full article
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Scheme 1

Open AccessShort Note
(E)-2-(1-Cyano-2-methoxy-2-oxoethylidene)-3,4-dioxo-1-(pyridin-1-ium-1-yl)cyclobutan-1-ide
Molbank 2017, 2017(3), M953; doi:10.3390/M953 -
Abstract
(E)-2-(1-Cyano-2-methoxy-2-oxoethylidene)-3,4-dioxo-1-(pyridin-1-ium-1-yl)cyclobutan-1-ide was obtained by a three-component reaction of squaric acid dichloride with pyridine and methyl cyanoacetate. Full article
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Open AccessShort Note
Ethyl 4-[5-(methoxymethyl)furan-2-yl]-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
Molbank 2017, 2017(3), M954; doi:10.3390/M954 -
Abstract
A one-pot multicomponent reaction has been used to synthesize the title compound, ethyl 4-[5-(methoxymethyl)furan-2-yl]-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate by PTSA catalyzed Biginelli reaction. The chemical structure of the product was confirmed by spectroscopic evidence, FTIR, HRESI-MS, 1D-, and 2D NMR. Full article
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Figure 1

Open AccessShort Note
Solvent-Mediated Synthesis of M(II)-Coordination Polymer Part 1: Crystal Structure of Poly(1,2-di(4-pyridyl)ethylene-k2N,N')-bis(1,4-benzenediacetato-k4O,O′,O′′,O′′')zinc(II)], C22H18ZnN2O4
Molbank 2017, 2017(3), M952; doi:10.3390/M952 -
Abstract
An interaction of water-methanol solution of sodium1,4-benzenediacetate (bda) and 4,4′-bipyridylethelene (bpee) with aqueous solution of Zn(NO3)2·6H2O at room temperature yielded colourless crystals of 1 after three weeks in a sealed glass tube. The compound with composition C
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An interaction of water-methanol solution of sodium1,4-benzenediacetate (bda) and 4,4′-bipyridylethelene (bpee) with aqueous solution of Zn(NO3)2·6H2O at room temperature yielded colourless crystals of 1 after three weeks in a sealed glass tube. The compound with composition C22H18ZnN2O4 crystallizes in monoclinic space group P21/c, with the following cell dimensions: a = 10.4566(2), b = 13.3085(2), c = 13.7189(2) Å, β = 101.491(1)°. In the structure of 1, two Zn(II) neighbours are connected by two bda ligands adopting chelating and bidentate-bridging coordination modes to form a dimeric unit (Zn2O8N4) with the Zn–Zn distance of 4.0432(6) Å. The carboxyl-bridged dimeric units are extended along the [001] direction by bpee co-ligands and further linked by bda ligand to form a three-dimensional network structure. The IR shows the characteristic bands of the carboxylates at 1611/1507 cm−1 and 1424/1373 cm−1, respectively, for asymmetric and symmetric stretching −CO2 vibrations. The separation ∆[νasym(CO2) − νsym(CO2)] values of 187 and 134 cm−1 are indicative of chelating and bidentate bridging coordination modes of the carboxylate to the metal centre. Full article
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Open AccessShort Note
Ethyl 5-(4-Bromophenyl)-4-methyl-1H-pyrrole-2-carboxylate
Molbank 2017, 2017(3), M951; doi:10.3390/M951 -
Abstract
This note describes a sequence converting an oxime-substituted pyrrolidine into a trisubstituted pyrrole structure. The synthetic route is based on a double chlorination of the pyrrolidine substrate followed by the base induced formation of both an imine and a nitrile oxide functionality. The
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This note describes a sequence converting an oxime-substituted pyrrolidine into a trisubstituted pyrrole structure. The synthetic route is based on a double chlorination of the pyrrolidine substrate followed by the base induced formation of both an imine and a nitrile oxide functionality. The latter reacts with an immobilized thiourea to yield an isothiocyanate which upon elimination generates the final pyrrole in an unprecedented cascade of events. Full article
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