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Molbank, Volume 2018, Issue 4 (December 2018) – 17 articles

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Short Note
5-(4-Bromophenyl)-7-(2,4-dimethoxyphenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine
Molbank 2018, 2018(4), M1037; https://doi.org/10.3390/M1037 - 17 Dec 2018
Viewed by 968
Abstract
A derivative of dihydrotetrazolopyrimidine has been successfully synthesized through a cyclocondensation reaction between a chalcone derivative with 5-aminotetrazole. The molecular structure of the title compound was established based on Fourier transform infrared spectra (FTIR), high-resolution mass spectrometry (HRMS), 1D and 2D nuclear magnetic [...] Read more.
A derivative of dihydrotetrazolopyrimidine has been successfully synthesized through a cyclocondensation reaction between a chalcone derivative with 5-aminotetrazole. The molecular structure of the title compound was established based on Fourier transform infrared spectra (FTIR), high-resolution mass spectrometry (HRMS), 1D and 2D nuclear magnetic resonance (NMR) spectrum. Full article
(This article belongs to the Section Organic Synthesis)
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Short Note
Tetrahydro-1,4-thiazine-3,5-dione
Molbank 2018, 2018(4), M1036; https://doi.org/10.3390/M1036 - 13 Dec 2018
Cited by 1 | Viewed by 912
Abstract
The X-ray structure of the title compound contains eight molecules in the unit cell which form the basis of a herringbone arrangement of hydrogen bonded ribbons. Full article
(This article belongs to the Section Structure Determination)
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Short Note
1-(2-Hydroxyethyl)imidazolidine-2-thione
Molbank 2018, 2018(4), M1035; https://doi.org/10.3390/M1035 - 03 Dec 2018
Cited by 3 | Viewed by 1027
Abstract
1-(2-Hydroxyethyl)imidazolidine-2-thione (1) was obtained as a product from an in situ reaction between N-(2-hydroxyethyl)ethylenediamine, carbon disulfide, potassium hydroxide, and di(4-fluorobenzyl)tin dichloride. Compound 1 was characterized by IR, UV, 1H, 13C{1H}, and 2D (COSY, NOESY, HSQC, and [...] Read more.
1-(2-Hydroxyethyl)imidazolidine-2-thione (1) was obtained as a product from an in situ reaction between N-(2-hydroxyethyl)ethylenediamine, carbon disulfide, potassium hydroxide, and di(4-fluorobenzyl)tin dichloride. Compound 1 was characterized by IR, UV, 1H, 13C{1H}, and 2D (COSY, NOESY, HSQC, and HMBC) NMR spectroscopies. The cyclic molecular structure was confirmed by single crystal X-ray crystallography which showed the five-membered ring to be non-planar and the π-electron density to be localized over the CN2S chromophore. In the crystal, thioamide–N–HO(hydroxy) and hydroxy–O–HS(thione) hydrogen bonds lead to supramolecular layers in the bc-plane. Full article
(This article belongs to the Section Structure Determination)
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Short Note
Synthesis and Structure Elucidation of N′-(4-Methoxybenzylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide
Molbank 2018, 2018(4), M1034; https://doi.org/10.3390/M1034 - 02 Dec 2018
Cited by 2 | Viewed by 1012
Abstract
N′-(4-Methoxybenzylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide (3) was synthesized in a yield of 88% from an acid-catalyzed reaction of 5-methyl-1-phenyl-1H-1,2,3- triazole-4-carbohydrazide and 4-methoxybenzaldehyde in ethanol under reflux for 2.5 h. The structure of 3 was confirmed by the data obtained from [...] Read more.
N′-(4-Methoxybenzylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide (3) was synthesized in a yield of 88% from an acid-catalyzed reaction of 5-methyl-1-phenyl-1H-1,2,3- triazole-4-carbohydrazide and 4-methoxybenzaldehyde in ethanol under reflux for 2.5 h. The structure of 3 was confirmed by the data obtained from infrared, nuclear magnetic resonance, mass spectroscopy, single crystal X-ray diffraction, and microanalysis. Full article
(This article belongs to the Section Structure Determination)
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Communication
Ureido Derivatives of Neoabietic Acid
Molbank 2018, 2018(4), M1033; https://doi.org/10.3390/M1033 - 29 Nov 2018
Viewed by 1220
Abstract
A series of ureido derivatives of neoabietic acid were synthesized by application of Curtius rearrangement reaction to neoabietic acid and amines. Structure characterization of these compounds was done by 1H-NMR, 13C-NMR and HRMS spectral analysis. Full article
(This article belongs to the Section Organic Synthesis)
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Communication
4′-(5-Methylfuran-2-yl)-2,2′:6′,2″-terpyridine: A New Ligand Obtained from a Biomass-Derived Aldehyde with Potential Application in Metal-Catalyzed Reactions
Molbank 2018, 2018(4), M1032; https://doi.org/10.3390/M1032 - 24 Nov 2018
Cited by 5 | Viewed by 1056
Abstract
The new ligand 4′-(5-methylfuran-2-yl)-2,2′:6′,2″-terpyridine (1) was prepared in one step from 2-acetylpyridine and 5-methylfurfural. The latter is an aldehyde that can be readily obtained from biomass. The new terpyridine molecule was characterized by 1H and 13C-NMR spectroscopy as well [...] Read more.
The new ligand 4′-(5-methylfuran-2-yl)-2,2′:6′,2″-terpyridine (1) was prepared in one step from 2-acetylpyridine and 5-methylfurfural. The latter is an aldehyde that can be readily obtained from biomass. The new terpyridine molecule was characterized by 1H and 13C-NMR spectroscopy as well as by elemental analyses and HR-MS. Owing to its chelating properties, this new terpyridine molecule was tested as a ligand in a metal-catalyzed reaction: The Ni-catalyzed dimerization of benzyl bromide. Full article
(This article belongs to the Section Organic Synthesis)
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Short Note
N-[2-(1H-Indol-3-yl)ethyl]-2-(4-isobutylphenyl)propanamide
Molbank 2018, 2018(4), M1031; https://doi.org/10.3390/M1031 - 22 Nov 2018
Cited by 1 | Viewed by 1357
Abstract
The compound in the title was prepared by reaction between tryptamine and ibuprofen using N,N′-dicyclohexylcarbodiimide as a “dehydrating” reagent. The structure of the newly synthesized compound was determined by nuclear magnetic resonance (NMR) (1H-NMR and 13C-NMR), UV, IR, and mass spectral data. Full article
(This article belongs to the Section Organic Synthesis)
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Short Note
N-[4-(1-Methyl-1H-imidazol-2-yl)-2,4′-bipyridin-2′-yl]benzene-1,4-diamine
Molbank 2018, 2018(4), M1030; https://doi.org/10.3390/M1030 - 16 Nov 2018
Cited by 2 | Viewed by 1123
Abstract
N-[4-(1-Methyl-1H-imidazol-2-yl)-2,4′-bipyridin-2′-yl]benzene-1,4-diamine was synthesized with a good yield by the reaction of 2′-chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine with 4-phenylenediamine. The functionalization of the pyridine was accomplished by a nucleophilic aromatic substitution (SNAr) reaction that afforded the target compound. The synthesized compound was characterized [...] Read more.
N-[4-(1-Methyl-1H-imidazol-2-yl)-2,4′-bipyridin-2′-yl]benzene-1,4-diamine was synthesized with a good yield by the reaction of 2′-chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine with 4-phenylenediamine. The functionalization of the pyridine was accomplished by a nucleophilic aromatic substitution (SNAr) reaction that afforded the target compound. The synthesized compound was characterized by chemical analysis, which includes nuclear magnetic resonance (NMR) (1H-NMR and 13C-NMR), Thin Layer Chromatography-Mass Spectrometry (TLC-MS), high- performance liquid chromatography (HPLC), Gas Chromatography-Mass Spectrometry (GC-MS), and elemental analysis. Full article
(This article belongs to the Section Organic Synthesis)
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Short Note
Ethyl 4-(2-fluorophenyl)-6-methyl-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
Molbank 2018, 2018(4), M1029; https://doi.org/10.3390/M1029 - 13 Nov 2018
Cited by 1 | Viewed by 1626
Abstract
The Biginelli reaction is a highly versatile reaction that leads to dihydropyrimidinones/thiones. This scaffold is reported as being a privileged structure due to its ability to interact with biological targets. Synthesis of ethyl 4-(2-fluorophenyl)-6-methyl-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate was achieved through the Biginelli reaction using [...] Read more.
The Biginelli reaction is a highly versatile reaction that leads to dihydropyrimidinones/thiones. This scaffold is reported as being a privileged structure due to its ability to interact with biological targets. Synthesis of ethyl 4-(2-fluorophenyl)-6-methyl-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate was achieved through the Biginelli reaction using a functionalized thiourea. In silico studies demonstrated that the compound title showed good potential for interacting with ecto-5’-nucleotidase, which has been considered as a target in designs for anti-cancer drugs. Full article
(This article belongs to the Special Issue Molecules from Multicomponent Reactions)
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Short Note
[O-Isopropyl-N-(4-nitrophenyl)thiocarbamato-κS]-(tri-4-tolylphosphine-κP)gold(I)
Molbank 2018, 2018(4), M1028; https://doi.org/10.3390/M1028 - 05 Nov 2018
Viewed by 983
Abstract
The synthesis, spectroscopic characterization and X-ray crystal structure of the title compound, (4-tolyl)3PAu[SC(O-i-Pr)=NC6H4NO2-4] (1) are described. Spectroscopy exhibited the expected features confirming the formation of the compound. The molecular structure of [...] Read more.
The synthesis, spectroscopic characterization and X-ray crystal structure of the title compound, (4-tolyl)3PAu[SC(O-i-Pr)=NC6H4NO2-4] (1) are described. Spectroscopy exhibited the expected features confirming the formation of the compound. The molecular structure of 1 confirms the expected linear P–Au–S coordination geometry defined by thiolate-S and phosphane-P atoms. The nearly 7° deviation from linearity is ascribed to the close approach of the imine-bound phenyl group, indicative of a semi-localized Auπ(arene) interaction. The three-dimensional molecular packing is consolidated by methyl- and tolyl-C–HO(nitro) and tolyl-C–Hπ(tolyl) interactions. Full article
(This article belongs to the Section Structure Determination)
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Short Note
(E)-3-[3-(4-Morpholinophenyl)acryloyl]-2H-chromen-2-one
Molbank 2018, 2018(4), M1027; https://doi.org/10.3390/M1027 - 29 Oct 2018
Cited by 6 | Viewed by 1271
Abstract
A new compound (E)-3-[3-(4-morpholinophenyl)acryloyl]-2H-chromen-2-one, a coumarin based chalcone derivative, has been successfully synthesized employing a molecular hybridization method through the reaction between 3-acetylcoumarin and 4-morpholinobenzaldehyde using a Claisen–Schmidt reaction using pTSA as a catalyst. The structure of the [...] Read more.
A new compound (E)-3-[3-(4-morpholinophenyl)acryloyl]-2H-chromen-2-one, a coumarin based chalcone derivative, has been successfully synthesized employing a molecular hybridization method through the reaction between 3-acetylcoumarin and 4-morpholinobenzaldehyde using a Claisen–Schmidt reaction using pTSA as a catalyst. The structure of the title compound was established using spectroscopic data FTIR, HRESI-MS, 1H- and 13C-NMR. The anticancer activity against breast cancer cells line T47D and cervix cancer cells line HeLa was determined using an MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Full article
(This article belongs to the Collection Molecules from Catalytic Processes)
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Short Note
2,3,4-Trioxo-1-(1H-pyrrolo[2,3-b]pyridin-7-ium-7yl)-cyclobutan-1-ide
Molbank 2018, 2018(4), M1026; https://doi.org/10.3390/M1026 - 12 Oct 2018
Cited by 1 | Viewed by 1007
Abstract
2,3,4-Trioxo-1-(1H-pyrrolo[2,3-b]pyridin-7-ium-7-yl)-cyclobutan-1-ide was obtained by reaction of squaric acid with 7-azaindole in acetic anhydride. Full article
(This article belongs to the Section Organic Synthesis)
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Scheme 1

Short Note
Dichlorido(η6-p-cymene)[tris(2-cyanoethyl)phosphine]ruthenium(II)
Molbank 2018, 2018(4), M1025; https://doi.org/10.3390/M1025 - 12 Oct 2018
Cited by 1 | Viewed by 1342
Abstract
The tris(2-cyanoethyl)phosphine (tcep) complex [RuCl2{P(CH2CH2CN)3}(η6-p-cymene)] (p-cymene = p-CH3C6H4iPr) was synthesised by the bridge-splitting reaction of the chlorido-dimer [RuCl2( [...] Read more.
The tris(2-cyanoethyl)phosphine (tcep) complex [RuCl2{P(CH2CH2CN)3}(η6-p-cymene)] (p-cymene = p-CH3C6H4iPr) was synthesised by the bridge-splitting reaction of the chlorido-dimer [RuCl2(η6-p-cymene)]2 with tcep. The complex was characterised by a single-crystal X-ray structure determination as well as NMR spectroscopy, ESI mass spectrometry, and microelemental analysis. X-ray crystallography shows the ruthenium atom is coordinated by p-cymene in a η6-fashion, two chlorides and the phosphorus atom of the tcep ligand with the donor set defining a distorted octahedral geometry. The ESI mass spectrometry study reveals that the complex readily forms negative ions [M + Cl] and [2M + Cl] by association with a chloride ion. Full article
(This article belongs to the Section Structure Determination)
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Communication
Purine-Furan and Purine-Thiophene Conjugates
Molbank 2018, 2018(4), M1024; https://doi.org/10.3390/M1024 - 08 Oct 2018
Cited by 1 | Viewed by 1128
Abstract
Furyl and thienyl moieties were introduced into a purine structure to elevate its fluorescence properties, while a trityl group was used to increase the amorphous properties of the purine compounds. The title compounds were prepared by a sequence involving a Mitsunobu, a S [...] Read more.
Furyl and thienyl moieties were introduced into a purine structure to elevate its fluorescence properties, while a trityl group was used to increase the amorphous properties of the purine compounds. The title compounds were prepared by a sequence involving a Mitsunobu, a SNAr and a Suzuki–Miyaura reaction and their photophysical properties were studied. Quantum yields in the solution reached up to 88% but only up to 5% in the thin layer. Full article
(This article belongs to the Section Organic Synthesis)
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Communication
1-Methyl-3-{4-[(4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl)benzyl]}-2-phenylindole
Molbank 2018, 2018(4), M1023; https://doi.org/10.3390/M1023 - 04 Oct 2018
Cited by 3 | Viewed by 1167
Abstract
The 1-methyl-3-{4-[(4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl)benzyl]}-2-phenylindole compound has been successfully synthesized via a multistep pathway starting from 2-phenylindole. Structure characterization of this new indole derivative was done by FTIR, 1H-NMR, 13C-NMR, and HRMS spectral analysis. The title compound showed high cytotoxic potential against [...] Read more.
The 1-methyl-3-{4-[(4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl)benzyl]}-2-phenylindole compound has been successfully synthesized via a multistep pathway starting from 2-phenylindole. Structure characterization of this new indole derivative was done by FTIR, 1H-NMR, 13C-NMR, and HRMS spectral analysis. The title compound showed high cytotoxic potential against five leukemia cell lines (K562, HL60, U937, U266, and Jurkat cell lines). Full article
(This article belongs to the Section Organic Synthesis)
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Communication
Synthesis of 4-(2H-[1,2,4]-Triazol-5-ylsulfanyl)-1,2-dihydropyrazol-3-one via Ring-Switching Hydrazinolysis of 5-Ethoxymethylidenethiazolo [3,2-b][1,2,4]triazol-6-one
Molbank 2018, 2018(4), M1022; https://doi.org/10.3390/M1022 - 01 Oct 2018
Cited by 5 | Viewed by 1675
Abstract
4-(1H-[1,2,4]-Triazol-5-ylsulfanyl)-1,2-dihydropyrazol-3-one (4) was synthesized with a yield of 55% via ring-switching hydrazinolysis of 5-ethoxymethylidenethiazolo[3,2-b][1,2,4] triazol-6-one (3) in ethanol medium. The initial 1H-[1,2,4]-triazole-3-thiol (1) was modified via a two-step reaction: S-alkylation [...] Read more.
4-(1H-[1,2,4]-Triazol-5-ylsulfanyl)-1,2-dihydropyrazol-3-one (4) was synthesized with a yield of 55% via ring-switching hydrazinolysis of 5-ethoxymethylidenethiazolo[3,2-b][1,2,4] triazol-6-one (3) in ethanol medium. The initial 1H-[1,2,4]-triazole-3-thiol (1) was modified via a two-step reaction: S-alkylation with chloroacetic acid under Williamson reaction conditions, and further one-pot cyclization–condensation with triethylorthoformate in the acetic anhydride medium, yielding compound 3. The structures of compounds 3 and 4 were confirmed by LC-MS, NMR spectra and a single X-ray diffraction analysis (for compound 4). Full article
(This article belongs to the Section Structure Determination)
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Short Note
6-[1-Acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-3-yl]-2(3H)-benzoxazolone
Molbank 2018, 2018(4), M1021; https://doi.org/10.3390/M1021 - 30 Sep 2018
Viewed by 1134
Abstract
The title compound, 6-[1-acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]-2(3H)-benzoxazolone, was synthesized by condensation of 6-[3-(4-methoxyphenyl)-2-propenoyl]-2(3H)-benzoxazolone (1) and hydrazine hydrate in acetic acid in 84% yield. The structure of the target compound was confirmed using 1H-NMR, 13C-NMR, IR, MS, and elemental analysis. Full article
(This article belongs to the Section Organic Synthesis)
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Scheme 1

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