Molbank

Open AccessCommunication

Synthesis of Catena-bis(μ-bromo)-(O-methyl-N-phenylthiocarbamate)-dicopper(I) and Its Reactivity towards PAr₃ (Ar = Ph, p-Tol)

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Molbank 2023, 2023(2), M1655; https://doi.org/10.3390/M1655 (registering DOI) - 31 May 2023

Abstract

In order to investigate the coordination chemistry of O-alkyl N-aryl thiocarbamate ligands toward coinage metals, CuBr was reacted with one equivalent of MeOC(=S)N(H)Ph L in MeCN solution to afford the 1D-polymeric title compound [{Cu(μ₂-Br)₂Cu}{μ₂-MeOC(=S)N(H)Ph} [...] Read more.

In order to investigate the coordination chemistry of O-alkyl N-aryl thiocarbamate ligands toward coinage metals, CuBr was reacted with one equivalent of MeOC(=S)N(H)Ph L in MeCN solution to afford the 1D-polymeric title compound [{Cu(μ₂-Br)₂Cu}{μ₂-MeOC(=S)N(H)Ph}₂]_n CP1. Compound 1 was characterized by IR spectroscopy and an elemental analysis. The formation of a polymeric 1D ribbon built upon μ₂-bridging bromido and thione ligands via the C=S bond was ascertained by a single-crystal X-ray diffraction study performed at 100 K. In the presence of PAr₃ (Ar = Ph, p-Tol), the polymer chain was broken to yield the mononuclear complexes [(Ar₃P)₂Cu{MeOC(=S)N(H)Ph}Br] C1 and C2. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessCommunication

Phosphine–Stibine and Phosphine–Stiborane peri-Substituted Donor–Acceptor Complexes

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Jan U. Bergsch

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Alexandra M. Z. Slawin

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Petr Kilian

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Brian A. Chalmers

Molbank 2023, 2023(2), M1653; https://doi.org/10.3390/M1653 - 30 May 2023

Abstract

Two novel Sb(III) and Sb(V) peri-substituted acenaphthene phosphorus−antimony compounds were prepared. The Sb(III) compound, 1, was prepared via reacting the organolithium precursor with dichloro(p-tolyl)Stibine, and 2 was prepared by the chlorination of 1. Both 1 and 2 were [...] Read more.

Two novel Sb(III) and Sb(V) peri-substituted acenaphthene phosphorus−antimony compounds were prepared. The Sb(III) compound, 1, was prepared via reacting the organolithium precursor with dichloro(p-tolyl)Stibine, and 2 was prepared by the chlorination of 1. Both 1 and 2 were characterized by multinuclear (¹H, ¹³C and ³¹P) NMR spectroscopy, and their molecular structures resolved by single-crystal X-ray diffraction. Both compounds show a dative P−Sb interaction with the antimony being the acceptor group in both cases owing to its Lewis acidity. Full article

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Open AccessShort Note

Isoetin 2′-O-α-l-arabinopyranoside-5′-O-β-d-glucopyranoside

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Mayra Galarza Pérez

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Fabian Fell

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Dimitrina Zheleva-Dimitrova

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Christian Zidorn

Molbank 2023, 2023(2), M1652; https://doi.org/10.3390/M1652 - 26 May 2023

Abstract

Isoetin derivatives are a rare class of flavonoids with a rather erratic occurrence across the plant kingdom. The Cichorieae tribe of the Asteraceae family has proven to be a rich source and a centre of chemical diversity of this class of compounds. Here, [...] Read more.

Isoetin derivatives are a rare class of flavonoids with a rather erratic occurrence across the plant kingdom. The Cichorieae tribe of the Asteraceae family has proven to be a rich source and a centre of chemical diversity of this class of compounds. Here, we describe the chromatographic isolation and mainly NMR-based structure elucidation of a previously undescribed isoetin derivative from Leontodon hispidus L. (Asteraceae, Cichorieae). The chemophenetic relevance is discussed briefly. Full article

(This article belongs to the Section Natural Products)

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Open AccessShort Note

1-(((6-(Methoxycarbonyl)-5-oxononan-4-yl)oxy)carbonyl)cyclopropane-1-carboxylic Acid

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Evgenii S. Gorlov

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Diana V. Shuingalieva

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Alexey I. Ilovaisky

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Vera A. Vil’

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Alexander O. Terent’ev

Molbank 2023, 2023(2), M1651; https://doi.org/10.3390/M1651 - 24 May 2023

Abstract

Here, we first report the 2′-acyloxy-1,3-dicarbonyl compound construction in a three-component oxidative reaction of alkyl ketene dimer with cyclic diacyl peroxide and trimethyl orthoformate. The discovered synthesis allows us to form 2′-functionalized 1,3-dicarbonyl compounds instead of the common 2-functionalized moiety. The reaction between [...] Read more.

Here, we first report the 2′-acyloxy-1,3-dicarbonyl compound construction in a three-component oxidative reaction of alkyl ketene dimer with cyclic diacyl peroxide and trimethyl orthoformate. The discovered synthesis allows us to form 2′-functionalized 1,3-dicarbonyl compounds instead of the common 2-functionalized moiety. The reaction between 4-butylidene-3-propyloxetan-2-one and cyclopropyl malonoyl peroxide proceeds in the presence of trifluoroacetic acid and trimethyl orthoformate at 120 °C for 1 h. The synthesized compound was characterized by NMR spectroscopy, mass spectrometry, and IR spectroscopy. Full article

(This article belongs to the Section Organic Synthesis)

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Scheme 1

Open AccessShort Note

(R)-(+)-3,5-Dinitro-N-(1-phenylethyl)benzothioamide

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Matthew G. Donahue

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Emily Crull

Molbank 2023, 2023(2), M1650; https://doi.org/10.3390/M1650 - 20 May 2023

Abstract

(R)-(+)-3,5-dinitro-N-(1-phenylethyl)benzothioamide 1 is a potential chiral solvating agent (CSA) for the spectral resolution of enantiomers via ¹H NMR spectroscopy. The single enantiomer of 1 was synthesized from commercially available (R)-(+)-a-methylbenzylamine 2 in two steps with 85% yield. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

5,6-Dihydro-[1,2,5]oxadiazolo[3,4-d]pyridazine-4,7-dione

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Timofey N. Chmovzh

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Karim S. Gaisin

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Oleg A. Rakitin

Molbank 2023, 2023(2), M1649; https://doi.org/10.3390/M1649 - 18 May 2023

Abstract

1,2,5-Chalcogenadiazoles fused with electron-withdrawing heterocycles have been actively investigated for the preparation of organic photovoltaic materials. [1,2,5]Oxadiazolo[3,4-d]pyridazines are much less studied than other chalcogenadiazolopyridazines due to their low availability. In this communication, we report our study showing that 5,6-dihydro-[1,2,5]oxadiazolo[3,4-d]pyridazine-4,7-dione, a key precursor for [...] Read more.

1,2,5-Chalcogenadiazoles fused with electron-withdrawing heterocycles have been actively investigated for the preparation of organic photovoltaic materials. [1,2,5]Oxadiazolo[3,4-d]pyridazines are much less studied than other chalcogenadiazolopyridazines due to their low availability. In this communication, we report our study showing that 5,6-dihydro-[1,2,5]oxadiazolo[3,4-d]pyridazine-4,7-dione, a key precursor for the synthesis of 4,7-dihalo-[1,2,5]oxadiazolo[3,4-d]pyridazines, is formed via the cyclization of 1,2,5-oxadiazole-3,4-dicarbohydrazide in hydrochloric acid. The structure of the newly synthesized compound was established by means of elemental analysis; high-resolution mass spectrometry; ¹H and ¹³C NMR; IR spectroscopy, and mass spectrometry. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Graphical abstract

Open AccessShort Note

5-(4-Chlorophenyl)-N,1-di-o-tolyl-1H-imidazole-2-amine

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Molbank 2023, 2023(2), M1648; https://doi.org/10.3390/M1648 - 17 May 2023

Abstract

A new 2-amino imidazole derivative, 5-(4-chlorophenyl)-N,1-di-o-tolyl-1H-imidazole-2-amine (3), has been synthesized using a green approach. The reaction was conducted in a ChCl (cholinium chloride)/urea eutectic mixture, which is a nature-inspired and environmentally friendly reaction medium. The proposed reaction mechanism involves [...] Read more.

A new 2-amino imidazole derivative, 5-(4-chlorophenyl)-N,1-di-o-tolyl-1H-imidazole-2-amine (3), has been synthesized using a green approach. The reaction was conducted in a ChCl (cholinium chloride)/urea eutectic mixture, which is a nature-inspired and environmentally friendly reaction medium. The proposed reaction mechanism involves the preliminary regioselective alkylation of the N_sp2 of guanidine (2), followed by an intramolecular condensation between the carbonyl moiety and the secondary N′_sp3. Finally, a tautomerization/aromatization step furnished the final product (3). Notably, 2-amino imidazole (3) could be isolated in high yield (91%), just by filtration from the DES/water mixture and subsequent crystallization; the remaining ChCl/urea could be recycled, after water removal, for four consecutive reactions without any significant drop in the (3) yield. The product has been fully characterized by ¹H, ¹³C, 2D ¹H-¹³C HSQC, and 2D ¹H-¹³C HMBC NMR; FT-IR spectroscopy; and EI-MS spectrometry. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Open AccessCommunication

Structural Elucidation of 2-(6-(Diethylamino)benzofuran-2-yl)-3-hydroxy-4H-chromen-4-one and Labelling of Mycobacterium aurum Cells

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Molbank 2023, 2023(2), M1647; https://doi.org/10.3390/M1647 - 16 May 2023

Abstract

Trehalose conjugates of 3-hydroxychromone (3HC) dyes have previously been utilized as fluorescence labels to detect metabolically active mycobacteria with a view to facilitating point-of-care detection of mycobacterial pathogens, especially Mycobacterium tuberculosis. We subjected the 3HC dye 2-(6-(diethylamino)benzofuran-2-yl)-3-hydroxy-4H-chromen-4-one (3HC-2) [...] Read more.

Trehalose conjugates of 3-hydroxychromone (3HC) dyes have previously been utilized as fluorescence labels to detect metabolically active mycobacteria with a view to facilitating point-of-care detection of mycobacterial pathogens, especially Mycobacterium tuberculosis. We subjected the 3HC dye 2-(6-(diethylamino)benzofuran-2-yl)-3-hydroxy-4H-chromen-4-one (3HC-2) to a combined X-ray crystallography and density functional theory (DFT) study, and conducted preliminary fluorescence labelling experiments with the model organism Mycobacterium aurum. In the crystal, 3HC-2 exhibits an s-cis conformation of the chromone and the benzofuran moieties about the central C–C bond. According to DFT calculations, the s-cis conformer is about 1.8 kcal mol⁻¹ lower in energy than the s-trans conformer. The solid-state supramolecular structure features hydrogen-bonded dimers and π…π stacking. Fluorescence microscopy revealed fluorescence of M. aurum cells treated with the dye trehalose conjugate 3HC-2-Tre in the GFP channel. It was concluded that s-cis is the preferred conformation of 3HC-2 and that the generally considered non-pathogenic M. aurum can be labelled with the fluorescence probe 3HC-2-Tre for convenient in vitro drug screening of new antimycobacterial agents. Full article

(This article belongs to the Section Structure Determination)

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Open AccessShort Note

4,4′-(((Perfluoropropane-2,2-diyl)bis(4,1-phenylene))bis(oxy))-bis(2,3,5,6-tetrafluoropyridine)

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Molbank 2023, 2023(2), M1644; https://doi.org/10.3390/M1644 - 15 May 2023

Abstract

The title compound was synthesized in near-quantitative yield using nucleophilic aromatic substitution of 4,4′-(hexafluoroisopropylidene)diphenol (BPAF) with perfluoropyridine (PFP). The purity and structure were determined by NMR (¹H, ¹³C, ¹⁹F), GC–EIMS, and single-crystal X-ray crystallography. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessCommunication

Synthesis and Structure of N-(1-(Bromomethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl)benzenesulfonamide

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Molbank 2023, 2023(2), M1645; https://doi.org/10.3390/M1645 - 15 May 2023

Abstract

A new bicyclic sulfonamide derivative, N-(1-(bromomethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl)benzenesulfonamide, was synthesized in the reaction of benzenesulfonamide and camphene in the presence of N-bromosuccinimide in acetonitrile. The proposed mechanism of investigated reaction involves the Wagner–Meerwein rearrangement stage. 3-(Bromomethylene)-2,2-dimethylbicyclo[2.2.1]heptane was isolated as a minor product. The products were [...] Read more.

A new bicyclic sulfonamide derivative, N-(1-(bromomethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl)benzenesulfonamide, was synthesized in the reaction of benzenesulfonamide and camphene in the presence of N-bromosuccinimide in acetonitrile. The proposed mechanism of investigated reaction involves the Wagner–Meerwein rearrangement stage. 3-(Bromomethylene)-2,2-dimethylbicyclo[2.2.1]heptane was isolated as a minor product. The products were characterized by IR, NMR spectroscopy, X-ray diffraction analysis, HRMS and elemental analysis data. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

1-(3-Isoselenocyanatopropyl)adamantane

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Dmitry Pitushkin

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Vladimir Burmistrov

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Gennady Butov

Molbank 2023, 2023(2), M1646; https://doi.org/10.3390/M1646 - 15 May 2023

Abstract

The title compound, 1-(3-isoselenocyanatopropyl)adamantane, was synthesized for the first time from 3-(adamantan-1-yl)propan-1-amine by the two-stage reaction with 1-(3-isocyanopropyl)adamantane as intermediate. The product was characterized by NMR, GC-MS, and elemental analysis. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

N,N,N-Triethyl-4-(1H-pyrrol-1-yl)butan-1-aminium Perchlorate

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Vasiliy V. Potapenkov

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Oleg V. Levin

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Daniil A. Lukyanov

Molbank 2023, 2023(2), M1643; https://doi.org/10.3390/M1643 - 13 May 2023

Abstract

Polypyrroles attract significant attention as the promising class of conductive polymers for the organic electronics, electrochemical energy-storage, photovoltaics, sensing and light-emitting devices due to their electrochemical and electrical properties. The attachment of the charged fragments to the pyrrole monomeric unit opens the route [...] Read more.

Polypyrroles attract significant attention as the promising class of conductive polymers for the organic electronics, electrochemical energy-storage, photovoltaics, sensing and light-emitting devices due to their electrochemical and electrical properties. The attachment of the charged fragments to the pyrrole monomeric unit opens the route to a water-soluble polypyrrole for improved solution processability. Here we report a scalable multigram synthesis of the N-substituted cationic pyrrole, N,N,N-triethyl-4-(1H-pyrrol-1-yl)butan-1-aminium perchlorate, which can be used for the preparation of the water-soluble cationic polypyrrole, in two steps with 81% overall yield. The resulting product was characterized by the ¹H and ¹³C, nuclear magnetic resonance (NMR), ESI-high-resolution mass spectrometry (ESI-HRMS) and Fourier-transform infrared spectroscopy (FTIR). Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessShort Note

Methyl 3,3-Bis[4-(dimethylamino)phenyl]-2,2-dimethylpropanoate

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Lara Mollà-Guerola

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Alejandro Baeza

Molbank 2023, 2023(2), M1642; https://doi.org/10.3390/M1642 - 09 May 2023

Abstract

The synthesis of methyl 3,3-bis[4-(dimethylamino)phenyl]-2,2-dimethylpropanoate is achieved by means of the alkylation of methyl isobutyrate silyl enol ether with bis[4-(dimethylamino)phenyl]methanol, facilitated by using 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a solvent and reaction promoter. The reaction proceeds smoothly to produce the mentioned compound in a good [...] Read more.

The synthesis of methyl 3,3-bis[4-(dimethylamino)phenyl]-2,2-dimethylpropanoate is achieved by means of the alkylation of methyl isobutyrate silyl enol ether with bis[4-(dimethylamino)phenyl]methanol, facilitated by using 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a solvent and reaction promoter. The reaction proceeds smoothly to produce the mentioned compound in a good yield via a metal and additive-free procedure. The corresponding ester is fully characterized. Full article

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Scheme 1

Open AccessCommunication

New 5-Chloro-Maleonitrile-Salen Ligand and Relative Co(II) Complex

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Giuseppe Trusso Sfrazzetto

Molbank 2023, 2023(2), M1639; https://doi.org/10.3390/M1639 - 08 May 2023

Abstract

Salen ligands and relative metal complexes are widely used in many fields, such as catalysis, sensing, optical and electronic materials. The introduction of a wide range of substituents in different positions, both in the salen scaffold and in the diamine bridge, allows the [...] Read more.

Salen ligands and relative metal complexes are widely used in many fields, such as catalysis, sensing, optical and electronic materials. The introduction of a wide range of substituents in different positions, both in the salen scaffold and in the diamine bridge, allows the tuning of chemical, catalytic and spectroscopic properties. In this contribution, we report the synthesis and characterization of a new salen ligand and relative Co(II) complex bearing a maleonitrile bridge and two chlorine atoms in the salen backbone. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

(η⁵-Pentamethylcyclopentadienyl)iridium{1,3-bis(2,3,4,5,6-pentafluorobenzyl)imidazolin-2-ylidene}dichloride

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Sravan K. Bandaru

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Andrew C. Marr

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Graham C. Saunders

Molbank 2023, 2023(2), M1641; https://doi.org/10.3390/M1641 - 08 May 2023

Abstract

In this paper, we report (η⁵-pentamethylcyclopentadienyl)iridium{1,3-bis(2,3,4,5,6-pentafluorobenzyl)imidazolin-2-ylidene}dichloride, 2, synthesized using a silver transfer agent generated from 1,3-bis(2,3,4,5,6-pentafluorobenzyl)imidazolium bromide. Compound 2 was characterized using ¹H and ¹⁹F NMR spectroscopy and mass spectrometry, and its structure was determined in a single-crystal X-ray diffraction study. Full article

(This article belongs to the Section Structure Determination)

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Open AccessShort Note

5-(1-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione

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Yuliya E. Ryzhkova

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Varvara M. Kalashnikova

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Fedor V. Ryzhkov

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Michail N. Elinson

Molbank 2023, 2023(2), M1640; https://doi.org/10.3390/M1640 - 08 May 2023

Abstract

Multicomponent reactions have been demonstrated as a promising tool for the creation of diverse molecular structures with enhanced efficiency, reduced waste, and a high atom economy. Arylglyoxal monohydrates with two different carbonyl groups are well known as worthwhile synthons in organic synthesis. 2-Pyrone [...] Read more.

Multicomponent reactions have been demonstrated as a promising tool for the creation of diverse molecular structures with enhanced efficiency, reduced waste, and a high atom economy. Arylglyoxal monohydrates with two different carbonyl groups are well known as worthwhile synthons in organic synthesis. 2-Pyrone and pyrimidine-2,4,6-trione are versatile building blocks for the synthesis of key intermediates in synthetic organic chemistry as well as in medicinal chemistry. A simple and efficient tandem Knoevenagel–Michael protocol for the synthesis of the previously unknown 5-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimet-hylpyrimidine-2,4,6(1H,3H,5H)-trione was elaborated. The suggested method is based on the multicomponent reaction of phenylglyoxal hydrate, 1,3-dimethylbarbituric acid, and 4-hydroxy-6-methyl-2H-pyran-2-one. The structure of the synthesized compound was proven by ¹H, ¹³C-NMR, and IR spectroscopy, mass spectrometry, and elemental analysis. A procedure for predicting the possible types of its biological activity was carried out for the title compound. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Scheme 1

Open AccessCommunication

Crystal Structures of a Series of Hydroxamic Acids

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Molbank 2023, 2023(2), M1637; https://doi.org/10.3390/M1637 - 07 May 2023

Abstract

The structure of four hydroxamic acids (HA) that show antifungal activities in complexes with several metals is revealed by single crystal diffraction. The structures of HA with C₂, C₆, C_10, and C₁₂ hydrocarbon chains are reported. The [...] Read more.

The structure of four hydroxamic acids (HA) that show antifungal activities in complexes with several metals is revealed by single crystal diffraction. The structures of HA with C₂, C₆, C_10, and C₁₂ hydrocarbon chains are reported. The smallest member of the series, N-hydroxyacetamide (HA2), crystallizes in the centrosymmetric space group P2₁/c while those with longer chain lengths N-hydroxyhexanamide (HA6), N-hydroxydecanamide (HA10), and N-hydroxydodecanamide (HA12) crystallize in the space group P2₁, and display remarkable packing. Full article

(This article belongs to the Section Structure Determination)

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Open AccessShort Note

(4Z,4′Z)-2,2′-(Ethane-1,2-diylbis(sulfanediyl))bis(1-phenyl)-4-(pyridin-2-ylmethylene)-1H-imidazol-5(4H)-one)dicopper(II) Tetrabromide

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Ahmed S. H. Al-Khazraji

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Molbank 2023, 2023(2), M1638; https://doi.org/10.3390/M1638 - 07 May 2023

Abstract

The title compound was characterized for the first time by a full range of physical methods including UV, FTIR, mass spectrometry and X-ray structure determination. The copper atoms have a distorted tetrahedral structure close to a trigonal pyramid. Full article

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Open AccessShort Note

7-((5-Bromo-1H-indol-3-yl)(4-methoxyphenyl)methyl)-1,3,5-triaza-7-phosphaadamantan-7-ium Tetrafluoroborate

by

Siva Sankar Murthy Bandaru

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Carola Schulzke

Molbank 2023, 2023(2), M1636; https://doi.org/10.3390/M1636 - 28 Apr 2023

Abstract

The novel organic salt 7-((5-bromo-1H-indol-3-yl)(4-methoxyphenyl)methyl)1,3,5-triaza-7-phosphaadamantan-7-ium tetrafluoroborate was synthesized from a Lewis acid (LA) and Lewis-base (LB) reaction between 1,3,5-triaza-7-phosphaadmantane (LB) and 5-bromo-3-(4-methoxybenzylidene)-3-H-indol-1-ium tetrafluoroborate (LA). The obtained Lewis acid base adduct, being the title compound, was analyzed and validated by ¹H, ¹³C, [...] Read more.

The novel organic salt 7-((5-bromo-1H-indol-3-yl)(4-methoxyphenyl)methyl)1,3,5-triaza-7-phosphaadamantan-7-ium tetrafluoroborate was synthesized from a Lewis acid (LA) and Lewis-base (LB) reaction between 1,3,5-triaza-7-phosphaadmantane (LB) and 5-bromo-3-(4-methoxybenzylidene)-3-H-indol-1-ium tetrafluoroborate (LA). The obtained Lewis acid base adduct, being the title compound, was analyzed and validated by ¹H, ¹³C, ³¹P, and ¹⁹F 1D-NMR-spectroscopy, ESI mass spectrometry, CHN-elemental analysis, and a single crystal X-ray diffraction investigation. Full article

(This article belongs to the Section Organic Synthesis)

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