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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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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Open AccessShort Note
2-[(2,6-Dimethylmorpholin-4-yl)methyl]-4-[(E)-2-{3-[(E)-2-{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4-hydroxy-5-methoxyphenyl}ethenyl]-1H-pyrazol-5-yl}ethenyl]-6-methoxyphenol
Molbank 2017, 2017(3), M949; doi:10.3390/M949 -
Abstract
A novel di-Mannich derivative of curcumin pyrazole, 2-[(2,6-dimethyl morpholin-4-yl)methyl]-4-[(E)-2-{3-[(E)-2-{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4-hydroxy-5-methoxyphenyl}ethenyl]-1H-pyrazol-5-yl}ethenyl]-6-methoxyphenol (2), has been synthesized through a Mannich reaction of curcumin pyrazole (1), formaldehyde, and 2,6-dimethylmorpholine. The structure of the synthesized compound was confirmed on
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A novel di-Mannich derivative of curcumin pyrazole, 2-[(2,6-dimethyl morpholin-4-yl)methyl]-4-[(E)-2-{3-[(E)-2-{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4-hydroxy-5-methoxyphenyl}ethenyl]-1H-pyrazol-5-yl}ethenyl]-6-methoxyphenol (2), has been synthesized through a Mannich reaction of curcumin pyrazole (1), formaldehyde, and 2,6-dimethylmorpholine. The structure of the synthesized compound was confirmed on the basis of FTIR, 1H-NMR, 13C-NMR, 2D Heteronuclear Single-Quantum Correlation (HSQC) and 2D Heteronuclear Multiple Bond Correlation (HMBC), and mass spectral data. The water solubility was evaluated and the result showed that compound 2 was three times more soluble than that of curcumin pyrazole (1) and curcumin. Full article
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Open AccessShort Note
(OC-6-35-A)-Aquadicarbonylchlorido[2-(2-pyridyl)-1,8-naphthyridine-κ;2N1,N2]ruthenium(II) hexafluoridophosphate 2,2-Bipyridine
Molbank 2017, 2017(3), M950; doi:10.3390/M950 -
Abstract
A dicarbonylruthenium(II) complex containing bidentate 2-(2-pyridyl)-1,8-naphthyridine, as well as monodentate aqua and chlorido ligands, were isolated and characterized using spectroscopic techniques and single crystal X-ray diffraction. These data indicate that geometrical isomerization occurs during the substitution reaction involving a superacid. Density functional theory
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A dicarbonylruthenium(II) complex containing bidentate 2-(2-pyridyl)-1,8-naphthyridine, as well as monodentate aqua and chlorido ligands, were isolated and characterized using spectroscopic techniques and single crystal X-ray diffraction. These data indicate that geometrical isomerization occurs during the substitution reaction involving a superacid. Density functional theory (DFT) calculations were performed on the plausible geometrical isomers. The DFT-optimized structures and calculated infrared spectra suggest that the experimentally obtained structure is stable. Full article
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Open AccessCommunication
Rac-2′,3a,6,6,6′,6′-Hexamethyl-3a,3b,6,7-tetra-hydrospiro-[benzo[2,3]cyclopropa[1,2-c]pyrazole-1,1′-cyclo-hepta[2,4]diene]
Molbank 2017, 2017(3), M948; doi:10.3390/M948 -
Abstract
This note describes a novel reaction cascade in which a tosylhydrazone derivative of eucarvone undergoes a non-classical dimerization process under basic conditions. The key step in this sequence is a dipolar cycloaddition between a diazo species and a transient cyclopropene. A proposed mechanism
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This note describes a novel reaction cascade in which a tosylhydrazone derivative of eucarvone undergoes a non-classical dimerization process under basic conditions. The key step in this sequence is a dipolar cycloaddition between a diazo species and a transient cyclopropene. A proposed mechanism for this sequence is presented that is supported by single crystal X-ray analysis of the resulting dimer. We believe this unique transformation is of note as it highlights a neat and efficient entry to complex polycyclic architectures containing an embedded pyrazoline moiety. Full article
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Open AccessCommunication
1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid
Molbank 2017, 2017(3), M947; doi:10.3390/M947 -
Abstract
1,2,3,4-Tetra-O-acetyl-β-d-mannuronic acid was synthesized in three steps from commercial d-mannose in 21% yield. Regioselective 6-O-tritylation followed by per-acetylation and 6-OTr removal using HBr/AcOH gave the required primary alcohol substrate, which was then oxidised to the target
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1,2,3,4-Tetra-O-acetyl-β-d-mannuronic acid was synthesized in three steps from commercial d-mannose in 21% yield. Regioselective 6-O-tritylation followed by per-acetylation and 6-OTr removal using HBr/AcOH gave the required primary alcohol substrate, which was then oxidised to the target compound using TEMPO/BAIB. None of the synthetic steps required column chromatography and the product was fully characterized by 1H-NMR, 13C-NMR, 2D NMR, MS and IR. Full article
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Open AccessShort Note
Ethyl 2-[2-(4-Nitrobenzoyl)-1H-indol-3-yl]acetate
Molbank 2017, 2017(3), M945; doi:10.3390/M945 -
Abstract
Ethyl 2-[2-(4-nitrobenzoyl)-1H-indol-3-yl]acetate was prepared in good yield and characterized by the aza-alkylation/intramolecular Michael cascade reaction of (E)-ethyl 3-[2-(tosylamino)phenyl]acrylate with 2-bromo-4′′-nitroacetophenone, followed by desulfonative dehydrogenation with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) The structure of the newly synthesized compound was determined using 1H-,
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Ethyl 2-[2-(4-nitrobenzoyl)-1H-indol-3-yl]acetate was prepared in good yield and characterized by the aza-alkylation/intramolecular Michael cascade reaction of (E)-ethyl 3-[2-(tosylamino)phenyl]acrylate with 2-bromo-4′′-nitroacetophenone, followed by desulfonative dehydrogenation with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) 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 AccessShort Note
Ethyl (E)-4-(2,4-Dimethoxyphenyl)-6-(2,4-dimethoxystyryl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
Molbank 2017, 2017(3), M946; doi:10.3390/M946 -
Abstract
A new compound belonging to the “heterostilbene” derivative, namely ethyl (E)-4-(2,4-dimethoxyphenyl)-6-(2,4-dimethoxystyryl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (2), has been successfully synthesized as an unprecedented side product of the Biginelli reaction between 2,4-dimethoxybenzaldehyde, ethyl acetoacetate and urea, employing PTSA as catalyst in reflux conditions and
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A new compound belonging to the “heterostilbene” derivative, namely ethyl (E)-4-(2,4-dimethoxyphenyl)-6-(2,4-dimethoxystyryl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (2), has been successfully synthesized as an unprecedented side product of the Biginelli reaction between 2,4-dimethoxybenzaldehyde, ethyl acetoacetate and urea, employing PTSA as catalyst in reflux conditions and using ethanol as solvent. The molecular structure of compound (2) was established by FTIR, HRESIMS, 1D and 2D NMR. Full article
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Figure 1

Open AccessShort Note
10a,11,11-Trimethyl-10a,11-dihydro-8H-benzo[e]imidazo[1,2-a]indol-9(10H)-one
Molbank 2017, 2017(2), M944; doi:10.3390/M944 -
Abstract
The alkylation of 1,1,2-trimethyl-1H-benzo[e]indole with 2-chloroacetamide, followed by work-up of the reaction mixture with a base and the subsequent treatment of a crude product with acetic acid gives 10a,11,11-trimethyl-10a,11-dihydro-8H-benzo[e]imidazo[1,2-a]indol-9(10H)-one. The structure
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The alkylation of 1,1,2-trimethyl-1H-benzo[e]indole with 2-chloroacetamide, followed by work-up of the reaction mixture with a base and the subsequent treatment of a crude product with acetic acid gives 10a,11,11-trimethyl-10a,11-dihydro-8H-benzo[e]imidazo[1,2-a]indol-9(10H)-one. The structure assignments were based on data from 1H, 13C, and 15N-NMR spectroscopy. The optical properties of the obtained compound were studied by UV–Vis and fluorescence spectroscopy. Full article
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Figure 1

Open AccessShort Note
N-(4-Nitrophenyl)-2-{2-[3-(4-chlorophenyl)-5-[4-(propan-2-yl)phenyl]-4,5-dihydro-1H-pyrazol-1-yl]-4-oxo-4,5-dihydro-1,3-thiazol-5-yl}acetamide
Molbank 2017, 2017(2), M943; doi:10.3390/M943 -
Abstract
In the present investigation, the synthesis and spectroscopic characterization of N-(4-nitrophenyl)-2-{2-[3-(4-chlorophenyl)-5-[4-(propan-2-yl)phenyl]-4,5-dihydro-1H-pyrazol-1-yl]-4-oxo-4,5-dihydro-1,3-thiazol-5-yl}acetamide (2) is performed. The title compound (2) is synthesized by the reaction of 3-(4-chlorophenyl)-5-[4-(propan-2-yl)phenyl]-4,5- dihydro-1H-pyrazole-1-carbothioamide (1) with N-(4-nitrophenyl)maleimide. The cyclization of title compound is evidenced by FT-IR, NMR, and LCMS data. Full article
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Open AccessShort Note
Ethyl 7-Methyl-1-(4-nitrophenyl)-5-phenyl-3-(thiophen-2-yl)-1,5-dihydro-[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate
Molbank 2017, 2017(2), M942; doi:10.3390/M942 -
Abstract
A novel compound, ethyl 7-methyl-1-(4-nitrophenyl)-5-phenyl-3-(thiophen-2-yl)-1,5-dihydro[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate (7) was synthesized by reaction of N-(4-nitrophenyl)thiophene-2-carbohydrazonoyl chloride (1) with ethyl 6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (2). The mechanism of the studied reaction is discussed and the assigned structure was confirmed by elemental
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A novel compound, ethyl 7-methyl-1-(4-nitrophenyl)-5-phenyl-3-(thiophen-2-yl)-1,5-dihydro[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate (7) was synthesized by reaction of N-(4-nitrophenyl)thiophene-2-carbohydrazonoyl chloride (1) with ethyl 6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (2). The mechanism of the studied reaction is discussed and the assigned structure was confirmed by elemental analysis and spectral data. Moreover, the in vitro antitumor activities against human lung (A-549) and human hepatocellular carcinoma (HepG-2) cell lines were determined by the MTT method, and the results indicated a high potency compared with the employed standard antitumor drug (Cisplatin). Full article
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Open AccessShort Note
7-Bromo-1-methyl-2-phenyl-1H-indole-3-carbonitrile
Molbank 2017, 2017(2), M941; doi:10.3390/M941 -
Abstract
The title compound was prepared by electrophilic aromatic substitution of 7-bromo-1-methyl-2-phenyl-1H-indole with NCTS (N-cyano-N-phenyl-p-toluenesulfonamide). The structural identity of the title compound was proven by elemental analysis and spectroscopic methods (IR, NMR, APCI-MS). Purity was assessed by two independent HPLC methods. Full article
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Scheme 1

Open AccessShort Note
4-Methoxy-3-(3-methylbut-2-en-1-yl)-7-[(3-methylbut-2-en-1-yl)oxy]quinolin-2(1H)-one from Melicope Moluccana T.G. Hartley
Molbank 2017, 2017(2), M939; doi:10.3390/M939 -
Abstract
4-Methoxy-3-(3-methylbut-2-en-1-yl)-7-[(3-methylbut-2-en-1-yl)oxy]quinolin-2(1H)-one (1) was isolated from the leaves of Melicope moluccana T.G. Hartley. The chemical structure of 1 was elucidated using mainly UV, IR, HRESIMS, 1D and 2D-NMR spectroscopy. Full article
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Figure 1

Open AccessShort Note
1-{4-[(Hexyloxy)methyl]pyridin-2-yl}ethanone
Molbank 2017, 2017(2), M940; doi:10.3390/M940 -
Abstract
A new member of the 2-acetylpyridine family has been prepared and characterized. Its synthesis is a two-step process starting from a pyridyl-alcohol in which the ketone moiety is protected as a cyclic acetal. Alkylation of the alcohol followed by hydrolysis of the acetal
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A new member of the 2-acetylpyridine family has been prepared and characterized. Its synthesis is a two-step process starting from a pyridyl-alcohol in which the ketone moiety is protected as a cyclic acetal. Alkylation of the alcohol followed by hydrolysis of the acetal afforded the title compound in 52% overall yield. Full article
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Open AccessShort Note
4-({4-[(2E)-3-(2,5-Dimethoxyphenyl)prop-2-enoyl]phenyl}amino)-4-oxobutanoic Acid
Molbank 2017, 2017(2), M938; doi:10.3390/M938 -
Abstract
A dimethoxy amide chalcone has been synthesized in a two-step reaction. First, an amine chalcone was synthesized by the reaction of 4′-aminoacetophenone and 2,5-dimethoxybenzaldehyde using 40% NaOH solution as a catalyst in ethanol, and then followed by amidation through the reaction of the
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A dimethoxy amide chalcone has been synthesized in a two-step reaction. First, an amine chalcone was synthesized by the reaction of 4′-aminoacetophenone and 2,5-dimethoxybenzaldehyde using 40% NaOH solution as a catalyst in ethanol, and then followed by amidation through the reaction of the formed chalcone and succinic anhydride. The structure of the target compound was established by FTIR, HR-MS, 1H- and 13C-NMR, and 2D-NMR spectral analysis. Full article
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Figure 1

Open AccessShort Note
Triphenylphosphine-(N,N-dimethyldithiocarbamato)-gold(I) Methanol Solvate
Molbank 2017, 2017(2), M937; doi:10.3390/M937 -
Abstract
Abstract: A gold(I) complex with a triphenylphosphine and a monodentate N,N-dimethyldithiocarbamate ligand was synthesized and characterized by Raman spectroscopy and single crystal X-ray diffraction. DFT calculations (Gaussian 09, PBE1PBE/Lanl2dz) were undertaken for a single complex in the gas phase. The DFT-optimized structure and
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Abstract: A gold(I) complex with a triphenylphosphine and a monodentate N,N-dimethyldithiocarbamate ligand was synthesized and characterized by Raman spectroscopy and single crystal X-ray diffraction. DFT calculations (Gaussian 09, PBE1PBE/Lanl2dz) were undertaken for a single complex in the gas phase. The DFT-optimized structure and calculated Raman spectrum are in good agreement with the crystal structure and the experimental spectrum. Assignments of the Raman peaks are based on these DFT calculations. Frontier molecular orbitals were calculated and their nature is discussed. Full article
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Figure 1

Open AccessShort Note
5,9,11-Trihydroxy-2,2-dimethyl-3-(2-methylbut-3-en-2-yl)pyrano[2,3-a]xanthen-12(2H)-one from the Stem Bark of Calophyllum tetrapterum Miq.
Molbank 2017, 2017(1), M936; doi:10.3390/M936 -
Abstract
A new pyranoxanthone namely 5,9,11-trihydroxy-2,2-dimethyl-3-(2-methylbut-3-en-2-yl)pyrano[2,3-a]xanthen-12(2H)-one (1) was isolated from the stem bark of Calophyllum tetrapterum Miq. The structure of compound 1 was determined by means of spectroscopic methods including UV, IR, HRESIMS, 1D and 2D NMR. Full article
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Figure 1

Open AccessShort Note
Methyl 2,3,6-tri-O-Benzoyl-4-O-(tert-butyldimethylsilyl)-β-d-galactopyranoside
Molbank 2017, 2017(1), M935; doi:10.3390/M935 -
Abstract
Methyl 2,3,6-tri-O-benzoyl-4-O-(tert-butyldimethylsilyl)-β-d-galactopyranoside was synthesized in 47% yield by the silylation of a partially benzoylated galactose derivative, prepared from methyl β-d-galactopyranoside. The product was characterized by 1H-NMR, 13C-NMR, IR and mass spectrometry. Full article
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Scheme 1