Molbank

Open AccessShort Note

Methyl 1,4-Benzodioxane-2-Carboxylates Mono-Nitrated at the Aromatic Ring

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Molbank 2023, 2023(2), M1661; https://doi.org/10.3390/M1661 (registering DOI) - 06 Jun 2023

Abstract

2-Substituted 1,4-benzodioxanes bearing one or more substituents at benzene are important templates in the design and synthesis of a large variety of biologically active compounds. One of the most straightforward synthetic strategies to prepare them in racemic form and with a 2-substituent susceptible [...] Read more.

2-Substituted 1,4-benzodioxanes bearing one or more substituents at benzene are important templates in the design and synthesis of a large variety of biologically active compounds. One of the most straightforward synthetic strategies to prepare them in racemic form and with a 2-substituent susceptible to further synthetically useful conversions is the condensation of commercially available methyl 2,3-dibromopropionate with already suitably functionalized catechol. Here, we obtain methyl 8- and 5-nitro-1,4-benzodioxane-2-carboxylate by reaction of methyl 2,3-dibromopropionate with 3-nitrocatechol. After separation, the two positional isomers could be unequivocally identified by HMBC NMR analysis. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessCommunication

Unexpected C–O Bond Cleavage by a Copper–Phosphido Compound

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Steven G. Dannenberg

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Rory Waterman

Molbank 2023, 2023(2), M1659; https://doi.org/10.3390/M1659 - 05 Jun 2023

Abstract

Copper methoxide compound IPrCuOMe was unexpectedly formed in a reaction of IPrCuPPh₂ with methyl acrylate. The alkoxide product was identified from the reaction mixture spectroscopically and structurally characterized. This C–O bond cleavage reaction likely depends on nucleophilicity of the Cu–P bond of [...] Read more.

Copper methoxide compound IPrCuOMe was unexpectedly formed in a reaction of IPrCuPPh₂ with methyl acrylate. The alkoxide product was identified from the reaction mixture spectroscopically and structurally characterized. This C–O bond cleavage reaction likely depends on nucleophilicity of the Cu–P bond of IPrCuPPh₂. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

Open AccessShort Note

Bis(3-aminobenzenesulfonato-N)-diaqua-bis(N,N’-dimethylformamide-O)-copper(II)

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Susanta Hazra

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Anirban Karmakar

Molbank 2023, 2023(2), M1658; https://doi.org/10.3390/M1658 - 04 Jun 2023

Abstract

Reaction of 3-aminobenzenesulfonic acid (HL1) with Cu(NO₃)₂·2.5H₂O in H₂O/DMF leads to the formation of the new bis(3-aminobenzenesulfonato-κN)-diaqua-bis(dimethylformamide-κO)-copper(II) complex [Cu(L1)₂(DMF)₂(H₂O)₂] (1) (HL1 [...] Read more.

Reaction of 3-aminobenzenesulfonic acid (HL1) with Cu(NO₃)₂·2.5H₂O in H₂O/DMF leads to the formation of the new bis(3-aminobenzenesulfonato-κN)-diaqua-bis(dimethylformamide-κO)-copper(II) complex [Cu(L1)₂(DMF)₂(H₂O)₂] (1) (HL1 = 3-aminobenzenesulfonic acid and DMF = N,N-dimethylformamide). Single crystal X-ray analysis reveals that the hexacoordinated copper(II) center adopts a distorted octahedral geometry with trans-oriented two 3-aminobenzenesulfonate ligands (L1⁻), two water and two dimethylformamide (DMF) molecules. Comparison of its crystal structure with that of the known bis(4-aminobenzenesulfonato-κN)diaquabis(dimethylformamide-κO)-copper(II) complex [Cu(L2)₂(DMF)₂(H₂O)₂] (2) (HL2 = 4-aminobenzenesulfonic acid) discloses that 1 and 2 are the isomers with an identical empirical formula (C₁₈H₃₀CuN₄O₁₀S₂) and equal numbers of same coordinated solvents (DMF and water). H-bonded supramolecular structures and their corresponding topological analyses revealed a 2D with 6-connected hxl/Shubnikov plane net (3,6) for 1 and a 3D with 8-connected bcu; 8/4/c1; sqc3 net for 2, which are completely different. Full article

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Open AccessShort Note

(E)-N’-(1-(Benzofuran-2-yl)ethylidene)-1-(4-Methoxyphenyl)-5-Methyl-1H-1,2,3-Triazole-4-Carbohydrazide

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Molbank 2023, 2023(2), M1657; https://doi.org/10.3390/M1657 - 03 Jun 2023

Abstract

The reaction of equimolar equivalents of 1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide (1) and 2-acetylbenzofuran (2) in anhydrous ethanol containing a catalytic amount of concentrated hydrochloric acid under reflux for 2 h gave (E)-N’-(1-(benzofuran-2-yl)ethylidene)-1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide (3 [...] Read more.

The reaction of equimolar equivalents of 1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide (1) and 2-acetylbenzofuran (2) in anhydrous ethanol containing a catalytic amount of concentrated hydrochloric acid under reflux for 2 h gave (E)-N’-(1-(benzofuran-2-yl)ethylidene)-1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide (3) in 86% yield. The structure of the title heterocycle 3 was confirmed using nuclear magnetic resonance and X-ray diffraction. Full article

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Open AccessShort Note

(E)-6-Hydroxy-2-oxo-2H-chromen-7-yl 3-(4-hydroxy-3-methoxyphenyl)acrylate

by

Yang-Heon Song

Molbank 2023, 2023(2), M1656; https://doi.org/10.3390/M1656 - 02 Jun 2023

Abstract

A hybrid compound 5: (E)-6-hydroxy-2-oxo-2H-chromen-7-yl 3-(4-hydroxy-3-methoxyphenyl)acrylate composed of (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (ferulic acid) 1 and 6,7-hydroxycoumarin (esculetin) 3 was prepared in a 61% yield by the esterification reaction of protected ferulic acid 2a with esculetin 3 in [...] Read more.

A hybrid compound 5: (E)-6-hydroxy-2-oxo-2H-chromen-7-yl 3-(4-hydroxy-3-methoxyphenyl)acrylate composed of (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (ferulic acid) 1 and 6,7-hydroxycoumarin (esculetin) 3 was prepared in a 61% yield by the esterification reaction of protected ferulic acid 2a with esculetin 3 in the presence of triethylamine in dichloromethane for 3 h, followed by deprotection using 3M HCl. The structure of compound 5 was confirmed by ¹H, ¹³C NMR spectroscopy, mass-spectrometry and elemental analysis. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessCommunication

Synthesis and Spectroscopic Characterization of Furan-2-Carbaldehyde-d

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Jonas Jaster

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Elias Dressler

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Robert Geitner

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Gregor Alexander Groß

Molbank 2023, 2023(2), M1654; https://doi.org/10.3390/M1654 - 31 May 2023

Abstract

Here, we present a protocol for the one-step synthesis of the title compound in quantitative yield using adapted Vilsmeier conditions. The product was characterized by ¹H-,²H-,¹³C-NMR-, as well as IR and Raman spectroscopy. Spectral data are given in detail. Full article

(This article belongs to the Section Organic Synthesis)

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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 - 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

by

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

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