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Molbank, Volume 2018, Issue 2 (June 2018)

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Open AccessShort Note 1-[5-(4-Ethoxyphenyl)-3-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one
Molbank 2018, 2018(2), M1000; https://doi.org/10.3390/M1000
Received: 23 May 2018 / Revised: 14 June 2018 / Accepted: 17 June 2018 / Published: 19 June 2018
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Abstract
The cyclization reaction of 3-(4-ethoxyphenyl)-1-(naphthalen-1-yl)prop-2-en-1-one (1) using hydrazine hydrate in acetic acid medium culminates, resulting in the title compound 1-[5-(4-ethoxyphenyl)-3-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one (2). The structure of the newly synthesized compound is determined by IR, 1H-NMR, 13C-NMR and
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The cyclization reaction of 3-(4-ethoxyphenyl)-1-(naphthalen-1-yl)prop-2-en-1-one (1) using hydrazine hydrate in acetic acid medium culminates, resulting in the title compound 1-[5-(4-ethoxyphenyl)-3-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one (2). The structure of the newly synthesized compound is determined by IR, 1H-NMR, 13C-NMR and mass spectral data. In order to evaluate the putative molecular interactions, the title compound (2) is docked against the active site of Cytochrome P450 14α-sterol demethylase (CYP51) from Mycobacterium tuberculosis. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessShort Note [(η5-pentamethylcyclopentadienyl)(3-fluoro-N-methylbenzylamine-к1,N)dichlorido]iridium(III)
Molbank 2018, 2018(2), M999; https://doi.org/10.3390/M999
Received: 17 May 2018 / Revised: 31 May 2018 / Accepted: 1 June 2018 / Published: 5 June 2018
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Abstract
A half-sandwich iridium(III) complex containing 3-fluoro-N-methylbenzylamine ligands has been obtained by reaction of one equivalent of [(η5-Cp*)IrCl2]2 (Cp* = pentamethylcyclopentadienyl) with two equivalent of 3-fluoro-N-methylbenzylamine in very good yield. The structure of this
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A half-sandwich iridium(III) complex containing 3-fluoro-N-methylbenzylamine ligands has been obtained by reaction of one equivalent of [(η5-Cp*)IrCl2]2 (Cp* = pentamethylcyclopentadienyl) with two equivalent of 3-fluoro-N-methylbenzylamine in very good yield. The structure of this complex was confirmed by X-ray crystallography, 1H-NMR, 13C-NMR spectroscopy, and elemental analysis. Full article
(This article belongs to the Section Structure Determination)
Open AccessShort Note Ethyl 5-methyl-7-(4-morpholinophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
Molbank 2018, 2018(2), M998; https://doi.org/10.3390/M998
Received: 8 May 2018 / Revised: 24 May 2018 / Accepted: 24 May 2018 / Published: 28 May 2018
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Abstract
A new compound belonging to a dihydrotetrazolopyrimidine derivative, that is, ethyl 5-methyl-7-(4-morpholinophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, was successfully synthesized using a Biginelli reaction between 4-morpholinobenzaldehyde, ethyl acetoacetate, and 5-aminotetrazole with p-toluenesulfonic acid (pTSA) as a catalyst in ethanol under reflux. The molecular
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A new compound belonging to a dihydrotetrazolopyrimidine derivative, that is, ethyl 5-methyl-7-(4-morpholinophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, was successfully synthesized using a Biginelli reaction between 4-morpholinobenzaldehyde, ethyl acetoacetate, and 5-aminotetrazole with p-toluenesulfonic acid (pTSA) as a catalyst in ethanol under reflux. The molecular structure of the title compound was characterized on the basis of spectroscopic evidence, using FTIR, HRESI-MS, 1H- and 13C-NMR, and 2D NMR. Full article
(This article belongs to the Special Issue Molecules from Catalytic Processes)
Open AccessFeature PaperCommunication 5,6,7,8-Tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine
Molbank 2018, 2018(2), M997; https://doi.org/10.3390/M997
Received: 13 May 2018 / Revised: 15 May 2018 / Accepted: 16 May 2018 / Published: 16 May 2018
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Abstract
Treating 1-fluoro-2-nitrobenzene (6) with N′-pentafluorophenylbenzohydrazide (7) and K2CO3 (1.1 equiv) in EtOH at ca. 110 °C (sealed tube) for 24 h affords 5,6,7,8-tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine (5) (36%) and N′-(2-nitrophenyl)-N
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Treating 1-fluoro-2-nitrobenzene (6) with N′-pentafluorophenylbenzohydrazide (7) and K2CO3 (1.1 equiv) in EtOH at ca. 110 °C (sealed tube) for 24 h affords 5,6,7,8-tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine (5) (36%) and N′-(2-nitrophenyl)-N′-(perfluorophenyl)benzohydrazide (3) (37%). The X-ray crystallography of 5,6,7,8-tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine (5) is provided. Microwave irradiation (100 W) of perfluorophenylbenzohydrazide 3 with K2CO3 (1.1 equiv) in THF at ca. 120 °C (sealed tube, 80 PSI) for 3 h gives oxadiazine 5 (85%), while reduction of the nitro group using Sn (4 equiv) in glacial acetic acid at ca. 20 °C for 30 min, followed by cyclodehydration at ca. 118 °C for 20 min and treatment with 2 M NaOH for 24 h resulted in 1-(perfluorophenyl)-3-phenyl-1,2,4-benzotriazin-4-yl (4) with 93% yield. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
Open AccessShort Note (E)-3-[4-(Pent-4-en-1-yloxy)phenyl]acrylicc Acid
Molbank 2018, 2018(2), M996; https://doi.org/10.3390/M996
Received: 1 May 2018 / Revised: 8 May 2018 / Accepted: 9 May 2018 / Published: 12 May 2018
Cited by 1 | PDF Full-text (1280 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
(E)-3-[4-(Pent-4-en-1-yloxy)phenyl]acetic acid is one of the useful components of liquid crystal materials which can be produced through Williamson ether synthesis by synthesizing 4-hydroxy-cinnamic acid and 5-bromo-1-pentene. Although Williamson ether synthesis is generally slow under conventional external heating conditions, microwave irradiation was
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(E)-3-[4-(Pent-4-en-1-yloxy)phenyl]acetic acid is one of the useful components of liquid crystal materials which can be produced through Williamson ether synthesis by synthesizing 4-hydroxy-cinnamic acid and 5-bromo-1-pentene. Although Williamson ether synthesis is generally slow under conventional external heating conditions, microwave irradiation was effective for significant acceleration of the etherification. Furthermore, we demonstrated the rapid and continuous synthesis of (E)-3-[4-(pent-4-en-1-yloxy)phenyl]acetic acid, using a microwave-assisted flow reactor developed by us, in which the blockage by salt precipitation was suppressed by the continuous addition of an aqueous methanol solution after the reaction cavity. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessShort Note 2,4-Bis[(2,6-diisopropylphenyl)imino]-3-methylpentan-3-ol
Molbank 2018, 2018(2), M995; https://doi.org/10.3390/M995
Received: 16 April 2018 / Revised: 8 May 2018 / Accepted: 11 May 2018 / Published: 12 May 2018
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Abstract
The compound 2,4-bis[(2,6-diisopropylphenyl)imino]-3-methylpentan-3-ol was synthesized with a yield of approximately 80% by the reaction of 2,4-bis(2,6-diisopropylphenylimino)pentan-3-one with trimethylaluminum, which was followed by hydrolysis with an aqueous NaOH solution. A chemoselective addition to the C=O bond occurred in this reaction. The structure was confirmed
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The compound 2,4-bis[(2,6-diisopropylphenyl)imino]-3-methylpentan-3-ol was synthesized with a yield of approximately 80% by the reaction of 2,4-bis(2,6-diisopropylphenylimino)pentan-3-one with trimethylaluminum, which was followed by hydrolysis with an aqueous NaOH solution. A chemoselective addition to the C=O bond occurred in this reaction. The structure was confirmed by X-ray crystallography. This new compound was also fully characterized by 1H, 13C-NMR spectroscopy and 1H-13C HSQC spectroscopy, mass spectrometry and elemental analysis. Full article
(This article belongs to the Section Structure Determination)
Open AccessShort Note N-(1-Deoxy-α-d-tagatopyranos-1-yl)-N-methylaniline (“d-Tagatose-N-methylaniline”)
Molbank 2018, 2018(2), M994; https://doi.org/10.3390/M994
Received: 17 April 2018 / Revised: 6 May 2018 / Accepted: 7 May 2018 / Published: 9 May 2018
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Abstract
Tagatosamines form in thermally-processed dairy products and contribute to the foods’ organoleptic and nutritional value. d-Tagatose-N-methylaniline (N-(1-deoxy-d-tagatos-1-yl)-N-methylaniline, 1-deoxy-1-(N-methylphenylamino)-d-tagatose) was synthesized from d-galactose via the Amadori rearrangement. In aqueous solution,
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Tagatosamines form in thermally-processed dairy products and contribute to the foods’ organoleptic and nutritional value. d-Tagatose-N-methylaniline (N-(1-deoxy-d-tagatos-1-yl)-N-methylaniline, 1-deoxy-1-(N-methylphenylamino)-d-tagatose) was synthesized from d-galactose via the Amadori rearrangement. In aqueous solution, it established an anomeric equilibrium consisting of 62.8% α-pyranose, 21.3% β-pyranose, 1.5% α-furanose, 8.1% β-furanose, and 6.2% acyclic keto tautomer. The crystalline α-pyranose anomer of d-tagatose-N-methylaniline adopted the 5C2 chair conformation. All hydroxyl and ring oxygen atoms and the amino nitrogen are involved in an extensive H-bonding network dominated by infinite homodromic chains. The Hirshfeld surface analysis suggests a significant contribution of non-polar intermolecular contacts to the crystal structure. Full article
(This article belongs to the Section Structure Determination)
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Open AccessFeature PaperShort Note Octahydro-1H,5H,7H-dipyrrolo[1,2-c:1′,2′-f][1,3,6]oxadiazocine-5-thione
Molbank 2018, 2018(2), M993; https://doi.org/10.3390/M993
Received: 28 March 2018 / Revised: 25 April 2018 / Accepted: 26 April 2018 / Published: 27 April 2018
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Abstract
A minor byproduct in the reaction of (S)-prolinol with thiophosgene in the presence of triethylamine is identified as a novel tricyclic dipyrrolidino-1,3,6-oxadiazocane-2-thione, the first example of such a ring system, and a representative of the uncommon, but useful 1,3,6-oxadiazocanes. A mechanism
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A minor byproduct in the reaction of (S)-prolinol with thiophosgene in the presence of triethylamine is identified as a novel tricyclic dipyrrolidino-1,3,6-oxadiazocane-2-thione, the first example of such a ring system, and a representative of the uncommon, but useful 1,3,6-oxadiazocanes. A mechanism is proposed for its formation. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Open AccessShort Note 1-Adamantylamidoxime
Molbank 2018, 2018(2), M992; https://doi.org/10.3390/M992
Received: 6 April 2018 / Revised: 13 April 2018 / Accepted: 17 April 2018 / Published: 19 April 2018
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Abstract
The title compound was prepared by the nucleophilic addition of hydroxylamine over 1-cyanoadamantane. The poor reactivity of the nitrile substrate, due to its scarcely electrophilic nature, prompted the need to employ several activating conditions. Energy supply via conventional heating, ultrasound, and microwave irradiation
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The title compound was prepared by the nucleophilic addition of hydroxylamine over 1-cyanoadamantane. The poor reactivity of the nitrile substrate, due to its scarcely electrophilic nature, prompted the need to employ several activating conditions. Energy supply via conventional heating, ultrasound, and microwave irradiation did not lead to product formation. Therefore, Lewis acid catalysis was attempted. Initial tests with ZnCl2 led to product formation in poor yields. Conversely, the use of AlCl3 led to the formation of the desired amidoxime in the moderate yield, which was further increased to an excellent yield by performing the reaction in a more concentrated medium. The structural identity of the title compound was proven by spectroscopic methods (IR, NMR). This compound was later employed as a starting material for the synthesis of 3,5-disubstituted 1,2,4-oxadiazole derivatives as potential 11β-HSD1 inhibitors. Full article
(This article belongs to the Special Issue Molecules from Catalytic Processes)
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Open AccessCommunication 1-[1-(4-Chlorobenzenesulfonyl)-1H-indole-3-yl]-3-[4-(pyridin-2-yl)piperazin-1-yl]propan-1-one
Molbank 2018, 2018(2), M991; https://doi.org/10.3390/M991
Received: 17 March 2018 / Revised: 13 April 2018 / Accepted: 16 April 2018 / Published: 18 April 2018
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Abstract
The title compound was prepared by an aza-Michael addition reaction between 1-[1-(4-chlorobenzenesulfonyl)-1H-indole-3-yl]prop-2-en-1-one and 2-piridylpiperazine catalyzed by SiO2. The structural identity of the title compound was proven by elemental analysis and spectroscopic methods (IR, NMR). The compound was assayed in
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The title compound was prepared by an aza-Michael addition reaction between 1-[1-(4-chlorobenzenesulfonyl)-1H-indole-3-yl]prop-2-en-1-one and 2-piridylpiperazine catalyzed by SiO2. The structural identity of the title compound was proven by elemental analysis and spectroscopic methods (IR, NMR). The compound was assayed in a binding assay at the 5-HT6 receptor, showing poor affinity. Full article
(This article belongs to the Special Issue Heterocycles)
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Open AccessCommunication Synthesis of 10-Methoxydiamantan-3-One
Molbank 2018, 2018(2), M990; https://doi.org/10.3390/M990
Received: 21 March 2018 / Revised: 1 April 2018 / Accepted: 4 April 2018 / Published: 9 April 2018
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Abstract
The synthesis of diamondoids particles up to 1–5 nm, in order to detect the nanostructure in the construction of nanoelectronic devices, for which the present of quantum limitation effects are theoretically presaged, is at the present time problematic. Diamondoids have many important physical
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The synthesis of diamondoids particles up to 1–5 nm, in order to detect the nanostructure in the construction of nanoelectronic devices, for which the present of quantum limitation effects are theoretically presaged, is at the present time problematic. Diamondoids have many important physical characteristics, including rigidity, lipophilicity, low strain energy, etc. Diamantane and their derivatives are also interesting for the study of nanoparticles. The present study deals with the development of the new synthetic route and diamantine-containing precursor for McMurry coupling reactions. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessShort Note (Z)-4-[2-(3,4-Difluorophenyl)hydrazono]-3-methyl-1H-pyrazol-5(4H)-one
Molbank 2018, 2018(2), M989; https://doi.org/10.3390/M989
Received: 24 February 2018 / Revised: 20 March 2018 / Accepted: 29 March 2018 / Published: 31 March 2018
PDF Full-text (2260 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The title compound (Z)-4-[2-(3,4-difluorophenyl)hydrazono]-3-methyl-1H-pyrazol-5(4H)-one 4 was synthesized by the reaction of ethyl 2-[2-(3,4-difluorophenyl)hydrazono]-3-oxobutanoate 3 with hydrazine hydrate. The diazotization of 3,4-difluoroaniline, followed by the treatment with ethyl acetoacetate, afforded intermediate 3. The synthesized compound 4 was
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The title compound (Z)-4-[2-(3,4-difluorophenyl)hydrazono]-3-methyl-1H-pyrazol-5(4H)-one 4 was synthesized by the reaction of ethyl 2-[2-(3,4-difluorophenyl)hydrazono]-3-oxobutanoate 3 with hydrazine hydrate. The diazotization of 3,4-difluoroaniline, followed by the treatment with ethyl acetoacetate, afforded intermediate 3. The synthesized compound 4 was characterized by FTIR, 1H-NMR, 13C-NMR and LCMS, and it showed synergistic anti-inflammatory, antiproliferative and antibacterial activities. Full article
(This article belongs to the Special Issue Heterocycles)
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