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Volume 2020, December

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Molbank, Volume 2020, Issue 1 (March 2020) – 13 articles

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Open AccessCommunication
Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block
Molbank 2020, 2020(1), M1111; https://doi.org/10.3390/M1111 - 18 Jan 2020
Abstract
Methyl [S-phenyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-α-d-mannopyranoside (R/S)S-oxide] uronate was synthesised from a thioglycoside mannosyl uronate donor in a 98% yield. By using one equivalent of meta-chloroperbenzoic acid (m-CPBA) as the sulphur oxidant, a smooth conversion to the diastereomeric [...] Read more.
Methyl [S-phenyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-α-d-mannopyranoside (R/S)S-oxide] uronate was synthesised from a thioglycoside mannosyl uronate donor in a 98% yield. By using one equivalent of meta-chloroperbenzoic acid (m-CPBA) as the sulphur oxidant, a smooth conversion to the diastereomeric sulfoxide products was achieved. The product was fully characterized by 1H, 13C and 2D NMR alongside MS analysis. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
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Open AccessCommunication
Half-Sandwich Arene-Osmium(II) Complexes with Phosphinite Ligands
Molbank 2020, 2020(1), M1110; https://doi.org/10.3390/M1110 - 17 Jan 2020
Abstract
The synthesis of a series of arene-osmium(II) complexes containing phosphinite-type ligands, namely, [OsCl2(η6-p-cymene){R2PO(CH2)nPh}] (R = Ph, n = 1 (4a), 2 (4b), 3 (4c); [...] Read more.
The synthesis of a series of arene-osmium(II) complexes containing phosphinite-type ligands, namely, [OsCl2(η6-p-cymene){R2PO(CH2)nPh}] (R = Ph, n = 1 (4a), 2 (4b), 3 (4c); R = iPr, n = 1 (5a), 2 (5b), 3 (5c)) and [OsCl2(η6-benzene){iPr2PO(CH2)2Ph}] (7), is presented. All these compounds were characterized by elemental analysis and multinuclear NMR spectroscopy (31P{1H}, 1H and 13C{1H}), and the structure of [OsCl2(η6-p-cymene){Ph2PO(CH2)3Ph}] (4c) unequivocally confirmed through a single-crystal X-ray diffraction study. Attempts to generate the tethered species [OsCl2{η6:κ1(P)-C6H5(CH2)nOPR2}] by intramolecular exchange of the coordinated arene in 4-5a-c or 7, upon thermal or MW heating, failed. Full article
(This article belongs to the Section Structure Determination)
Open AccessShort Note
2,9-Dimethyl-11-(3-pentadecylphenoxy)dibenzo[c,f][1,2,5]dithiaphosphepine 11-oxide
Molbank 2020, 2020(1), M1109; https://doi.org/10.3390/M1109 - 14 Jan 2020
Abstract
2,9-Dimethyl-11-(3-pentadecylphenoxy)dibenzo[c,f][1,2,5]dithiaphosphepine 11-oxide was synthesized (yield 50%) by a two-step procedure. The first step starts with a benzothiadiphosphole and bis-Grignard reagent, and the second step consists of adding the sodium salt of a derivative of cardanol. The structure of newly [...] Read more.
2,9-Dimethyl-11-(3-pentadecylphenoxy)dibenzo[c,f][1,2,5]dithiaphosphepine 11-oxide was synthesized (yield 50%) by a two-step procedure. The first step starts with a benzothiadiphosphole and bis-Grignard reagent, and the second step consists of adding the sodium salt of a derivative of cardanol. The structure of newly synthesized compound was elucidated based on 1H-NMR, 13C-NMR, 31P-NMR, IR, Electron Spray Ionization (ESI)–MS, Gas Chromatography-Mass Spectroscopy (GC–MS), and Electron Spray Ionization-High Resolution Mass Spectroscopy (ESI–HRMS). Full article
Open AccessCommunication
Unexpected Formation of Oxetanes during the Synthesis of Dodeco-6,7-diuloses
Molbank 2020, 2020(1), M1108; https://doi.org/10.3390/M1108 - 14 Jan 2020
Abstract
During the synthesis of symmetrical dodeco-6,7-diuloses that are potential candidates for inhibition of glycosidases, an unanticipated epoxide-oxetane rearrangement was observed. A bicyclic sugar consisting of a glycal moiety and an anomeric esterified furanose was oxidized under epoxidation conditions (mCPBA/KF). The isolation [...] Read more.
During the synthesis of symmetrical dodeco-6,7-diuloses that are potential candidates for inhibition of glycosidases, an unanticipated epoxide-oxetane rearrangement was observed. A bicyclic sugar consisting of a glycal moiety and an anomeric esterified furanose was oxidized under epoxidation conditions (mCPBA/KF). The isolation of the pure epoxide was not possible since a rapid reversible conversion accompanied by the migration of the ester group took place and resulted in the formation of an unusual oxetane-bridged disaccharide scaffold. X-ray diffractometric structure elucidation and the suggested mechanism of the rearrangement are provided. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
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Open AccessCommunication
Dimethyl 2-{[2-(2-Methoxy-1-methoxycarbonyl-2-oxoethyl)-4,5,7-trimethoxy-3-(2,4,5-trimethoxyphenyl)-2,3-dihydro-1H-inden-1-yl]methyl}malonate
Molbank 2020, 2020(1), M1107; https://doi.org/10.3390/M1107 - 14 Jan 2020
Abstract
A simple synthetic approach to dimethyl 2-{[2-(2-methoxy-1-methoxycarbonyl-2-oxoethyl)-4,5,7-trimethoxy-3-(2,4,5-trimethoxyphenyl)-2,3-dihydro-1H-inden-1-yl]methyl}malonate has been developed, based on a B(C6F5)3-induced domino dimerization of 2-(2,4,5-trimethoxyphenyl)cyclopropane-1,1-diester. Full article
(This article belongs to the Section Organic Synthesis)
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2-(Bicyclo[4.2.0]octa-1,3,5-trien-3-yl)-adamantan-2-ol
Molbank 2020, 2020(1), M1106; https://doi.org/10.3390/M1106 - 10 Jan 2020
Abstract
A new adamantan-2-ol with a 2-bicyclo[4.2.0]octa-1,3,5-trien-3-yl substituent in the position 2 was synthesized via two stage synthesis starting from benzocyclobutene and adamatan-2-one. The structure of the title compound was determined using 1H-and 13C-NMR, HRMS and XRD. Full article
Open AccessCommunication
(2Sp,4R,8Sp)-4-Methyl-1-phenyl-diferroceno-5-Z-ethylene-1-phosphinoxide
Molbank 2020, 2020(1), M1105; https://doi.org/10.3390/M1105 - 08 Jan 2020
Abstract
We present a synthesis of the title compound, a homochiral diferroceno cycle intended for use in asymmetric catalysis. We present a hydrovinylation protocol, which allows the production of the title compound in two steps from a known diferrocenyl precursor. We obtained one of [...] Read more.
We present a synthesis of the title compound, a homochiral diferroceno cycle intended for use in asymmetric catalysis. We present a hydrovinylation protocol, which allows the production of the title compound in two steps from a known diferrocenyl precursor. We obtained one of two possible diastereomers selectively and propose a plausible regio- and stereoselective reaction mechanism. Full article
(This article belongs to the Section Organic Synthesis)
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N′-Acetyl-3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine-4-carbohydrazide
Molbank 2020, 2020(1), M1104; https://doi.org/10.3390/M1104 - 07 Jan 2020
Abstract
Synthesis of N′-acetyl-3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine-4-carbohydrazide from the phenyl acetates of 3-acetyl-5-(3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine-4-yl)-2,3-dihydro-1,3,4-oxadiazol-2-yl in alkaline medium and its characterization by spectroscopic methods. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
Open AccessShort Note
2-Hydroxy-N′-(4-Fluorobenzoyl)Benzohydrazide
Molbank 2020, 2020(1), M1103; https://doi.org/10.3390/M1103 - 24 Dec 2019
Abstract
2-Hydroxy-N′-(4-fluorobenzoyl)benzohydrazide was synthesized in two steps using methyl salicylate as the starting material. The reaction took place via microwave-aided hydrazinolysis, followed by acylation using 4-fluorobenzoyl chloride at low temperature to yield the target compound. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessShort Note
Bicyclo[4.2.0]octa-1,3,5-trien-3-yl-dimethyl((E)-styryl)-silane
Molbank 2020, 2020(1), M1102; https://doi.org/10.3390/M1102 - 23 Dec 2019
Abstract
Bicyclo[4.2.0]octa-1,3,5-trien-3-yl-dimethyl-((E)-styryl)-silane was synthesized via three stage synthesis starting from benzocyclobutene and (2-bromo-vinyl)-benzene. The structure of the product was determined using 1H- and 13C-NMR and HRMS. Full article
Open AccessShort Note
Bis(N′-(3-chlorobenzoyl)isonicotinohydrazide)Iron(III) Complex
Molbank 2020, 2020(1), M1101; https://doi.org/10.3390/M1101 - 20 Dec 2019
Abstract
The bis(N′-(3-chlorobenzoyl)isonicotinohydrazide)iron(III) complex was synthesised from N′-(3-chlorobenzoyl)isonicotinohydrazide and iron(III) metal by reflux in an ethanol solution. The title compound was characterised by Fourier-transform infrared spectroscopy (FTIR) spectroscopy, differential thermal analysis/thermogravimetric analysis (DTA/TGA) and UV-visible spectroscopy. The results indicate that coordination [...] Read more.
The bis(N′-(3-chlorobenzoyl)isonicotinohydrazide)iron(III) complex was synthesised from N′-(3-chlorobenzoyl)isonicotinohydrazide and iron(III) metal by reflux in an ethanol solution. The title compound was characterised by Fourier-transform infrared spectroscopy (FTIR) spectroscopy, differential thermal analysis/thermogravimetric analysis (DTA/TGA) and UV-visible spectroscopy. The results indicate that coordination of the iron(III) ion to the ligand increased its thermal stability. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessCommunication
Synthesis of N-Heterocyclic Analogues of 28-O-Methyl Betulinate, and Their Antibacterial and Antifungal Properties
Molbank 2020, 2020(1), M1100; https://doi.org/10.3390/M1100 - 19 Dec 2019
Abstract
The paper presents the results on the one-pot pyridine quaternization using betulinic 28-O-methyl ester (1) and Tempo+Br3 cation followed by reduction of the resulting salt (2) to 1,2,5,6-tetrahydropyridine derivative (3). The [...] Read more.
The paper presents the results on the one-pot pyridine quaternization using betulinic 28-O-methyl ester (1) and Tempo+Br3 cation followed by reduction of the resulting salt (2) to 1,2,5,6-tetrahydropyridine derivative (3). The structures of new compounds are confirmed by means of 1D and 2D-NMR spectroscopy, as well as MALDI TOF/TOF spectrometry. The derivatives 2 and 3 are active against S. aureus at the minimum inhibitory concentration (MIC) of 4 μg/mL and 16 μg/mL, correspondingly. Full article
(This article belongs to the Section Natural Products)
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N-(2-Hydroxy-1,1-dimethylethyl)-3-methylbenzamide
Molbank 2020, 2020(1), M1099; https://doi.org/10.3390/M1099 - 19 Dec 2019
Cited by 1
Abstract
The title compound, N-(2-hydroxy-1,1-dimethylethyl)-3-methylbenzamide was synthesized by reacting 3-methylbenzoyl chloride or 3-methylbenzoic acid with 2-amino-2-methyl-1-propanol. In the present report, the synthesized target compound was fully characterized by various spectroscopic methods (1H NMR, 13C NMR, IR, GC-MS), its composition confirmed [...] Read more.
The title compound, N-(2-hydroxy-1,1-dimethylethyl)-3-methylbenzamide was synthesized by reacting 3-methylbenzoyl chloride or 3-methylbenzoic acid with 2-amino-2-methyl-1-propanol. In the present report, the synthesized target compound was fully characterized by various spectroscopic methods (1H NMR, 13C NMR, IR, GC-MS), its composition confirmed by elemental analysis, and its structure determined and confirmed by X-ray analysis. The importance of this compound lies in its possession of an N,O-bidentate directing group. Such a structural motif is potentially suitable for metal-catalyzed C–H bond functionalization reactions. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
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