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Molbank, Volume 2018, Issue 2 (June 2018) – 12 articles

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6 pages, 1998 KiB  
Short Note
1-[5-(4-Ethoxyphenyl)-3-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one
by Sangeetha Karanth, Badiadka Narayana, Jayashree Avvadukkam and Balladka Kunhanna Sarojini
Molbank 2018, 2018(2), M1000; https://doi.org/10.3390/M1000 - 19 Jun 2018
Viewed by 2181
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 [...] Read more.
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)
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5 pages, 750 KiB  
Short Note
[(η5-pentamethylcyclopentadienyl)(3-fluoro-N-methylbenzylamine-к1,N)dichlorido]iridium(III)
by Deliang Kong, Lihua Guo, Shumiao Zhang, Xicheng Liu and Zhe Liu
Molbank 2018, 2018(2), M999; https://doi.org/10.3390/M999 - 05 Jun 2018
Cited by 1 | Viewed by 2501
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 [...] Read more.
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)
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5 pages, 814 KiB  
Short Note
Ethyl 5-methyl-7-(4-morpholinophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
by Hery Suwito, Noorma Kurnyawaty, Kautsar Ul Haq, Abdulloh Abdulloh and Indriani Indriani
Molbank 2018, 2018(2), M998; https://doi.org/10.3390/M998 - 28 May 2018
Cited by 3 | Viewed by 2635
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 [...] Read more.
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 Collection Molecules from Catalytic Processes)
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8 pages, 1191 KiB  
Communication
5,6,7,8-Tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine
by Georgia A. Zissimou, Andreas Kourtellaris and Panayiotis A. Koutentis
Molbank 2018, 2018(2), M997; https://doi.org/10.3390/M997 - 16 May 2018
Viewed by 2532
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 [...] Read more.
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)
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5 pages, 1280 KiB  
Short Note
(E)-3-[4-(Pent-4-en-1-yloxy)phenyl]acrylicc Acid
by Hiromichi Egami, Taira Sawairi, Souma Tamaoki, Noriyuki Ohneda, Tadashi Okamoto, Hiromichi Odajima and Yoshitaka Hamashima
Molbank 2018, 2018(2), M996; https://doi.org/10.3390/M996 - 12 May 2018
Cited by 8 | Viewed by 3161
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 [...] Read more.
(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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5 pages, 1125 KiB  
Short Note
2,4-Bis[(2,6-diisopropylphenyl)imino]-3-methylpentan-3-ol
by Wenting Sun, Wenyu Kong, Qing Du, Shumiao Zhang, Lihua Guo and Zhe Liu
Molbank 2018, 2018(2), M995; https://doi.org/10.3390/M995 - 12 May 2018
Viewed by 2160
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 [...] Read more.
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)
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9 pages, 5006 KiB  
Short Note
N-(1-Deoxy-α-d-tagatopyranos-1-yl)-N-methylaniline (“d-Tagatose-N-methylaniline”)
by Valeri V. Mossine, Charles L. Barnes and Thomas P. Mawhinney
Molbank 2018, 2018(2), M994; https://doi.org/10.3390/M994 - 09 May 2018
Viewed by 2382
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, [...] Read more.
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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5 pages, 745 KiB  
Short Note
Octahydro-1H,5H,7H-dipyrrolo[1,2-c:1′,2′-f][1,3,6]oxadiazocine-5-thione
by R. Alan Aitken and Karamat Ali
Molbank 2018, 2018(2), M993; https://doi.org/10.3390/M993 - 27 Apr 2018
Cited by 1 | Viewed by 2636
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 [...] Read more.
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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6 pages, 1153 KiB  
Short Note
1-Adamantylamidoxime
by Benjamín Diethelm, Carlos F. Lagos and Gonzalo Recabarren-Gajardo
Molbank 2018, 2018(2), M992; https://doi.org/10.3390/M992 - 19 Apr 2018
Viewed by 3074
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 [...] Read more.
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 Collection Molecules from Catalytic Processes)
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7 pages, 2198 KiB  
Communication
1-[1-(4-Chlorobenzenesulfonyl)-1H-indole-3-yl]-3-[4-(pyridin-2-yl)piperazin-1-yl]propan-1-one
by Benjamín Diethelm, Sebastián Almendras and Gonzalo Recabarren-Gajardo
Molbank 2018, 2018(2), M991; https://doi.org/10.3390/M991 - 18 Apr 2018
Cited by 1 | Viewed by 10215
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 [...] Read more.
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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4 pages, 369 KiB  
Communication
Synthesis of 10-Methoxydiamantan-3-One
by Ngo Trung Hoc, A. A. Fokin and V. N. Rodionov
Molbank 2018, 2018(2), M990; https://doi.org/10.3390/M990 - 09 Apr 2018
Cited by 1 | Viewed by 2262
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 [...] Read more.
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)
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9 pages, 2260 KiB  
Short Note
(Z)-4-[2-(3,4-Difluorophenyl)hydrazono]-3-methyl-1H-pyrazol-5(4H)-one
by Billava Jayappa Mohan, Balladka Kunhanna Sarojini, Badiadka Narayana and Enumadishetty Srinivasulu Sindhu Priya
Molbank 2018, 2018(2), M989; https://doi.org/10.3390/M989 - 31 Mar 2018
Cited by 1 | Viewed by 3626
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 [...] Read more.
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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