Molbank

11 pages, 3378 KiB

Open AccessCommunication

[Palladium-decabismuth(4+)]-tetrakis(tetrachloridoaluminate) Cluster Compound, [Pd@Bi₁₀][AlCl₄]₄: Synthesis, Crystal Structure, and Electronic Structure

by S. M. Gayomi K. Samarakoon and Sviatoslav Baranets

Molbank 2025, 2025(2), M2020; https://doi.org/10.3390/M2020 (registering DOI) - 9 Jun 2025

Abstract

Black, needle-like single crystals of [Pd@Bi₁₀][AlCl₄]₄ were synthesized in a one-pot reaction between PdCl₂, Bi, and BiCl₃ at 180 °C in the Lewis acidic ionic liquid (LAIL) medium [BMIm]Cl∙4.2AlCl₄ (BMIm = 1-n-butyl-3-methylimidazolium). [...] Read more.

Black, needle-like single crystals of [Pd@Bi₁₀][AlCl₄]₄ were synthesized in a one-pot reaction between PdCl₂, Bi, and BiCl₃ at 180 °C in the Lewis acidic ionic liquid (LAIL) medium [BMIm]Cl∙4.2AlCl₄ (BMIm = 1-n-butyl-3-methylimidazolium). Single-crystal X-ray diffraction revealed that the compound crystallizes in the triclinic space group P

\bar{1}

with the unit cell parameters a = 11.0233(5) Å, b = 26.1892(14) Å, c = 26.2687(14) Å, α = 90.842(2)°, β = 92.1940(10)°, γ = 91.164(2)°, closely matching its platinum-containing analog. The structure features pentagonal antiprismatic [Pd@Bi₁₀]⁴⁺ cluster cations charge-balanced by tetrahedral [AlCl₄]⁻ anions. Bonding and charge analysis reveal unoptimized Pd–Bi and strong Bi–Bi covalent interactions consistent with electronegativity trends and the previously reported host–guest model. Electronic structure calculations performed with the TB-LMTO-ASA program show that [Pd@Bi₁₀][AlCl₄]₄ exhibits semiconducting behavior, suggesting a bandgap opening of 0.71 eV. Full article

(This article belongs to the Section Structure Determination)

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6 pages, 686 KiB

Open AccessCommunication

A Neutral Heteroleptic Cu(I) Complex with Diimine and Diphosphine Ligands

by Xiaojuan Sun, Ruilong Sheng, Marijana Petkovic, Jolanta Jaśkowska and Zhiqiang Wang

Molbank 2025, 2025(2), M2019; https://doi.org/10.3390/M2019 - 6 Jun 2025

Viewed by 97

Abstract

Developing organic luminescent materials with the advantages of low cost, high thermal stability, and strong emission performance is incredibly desirable. In this work, we synthesized a new neutral heteroleptic Cu(I) complex characterized by single-crystal X-ray diffraction, FT-IR, NMR, and MALDI-TOF-MS. The neutral heteroleptic [...] Read more.

Developing organic luminescent materials with the advantages of low cost, high thermal stability, and strong emission performance is incredibly desirable. In this work, we synthesized a new neutral heteroleptic Cu(I) complex characterized by single-crystal X-ray diffraction, FT-IR, NMR, and MALDI-TOF-MS. The neutral heteroleptic Cu(I) complex has a typical distorted tetrahedral configuration, and the complex molecules are connected into 1D chains via C-H···π interactions in crystal. Full article

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Graphical abstract

9 pages, 2019 KiB

Open AccessShort Note

5,5′-Di((E)-buta-1,3-dien-1-yl)-2,2′,3,3′-tetramethoxy-1,1′-biphenyl

by Maria Antonietta Dettori, Davide Fabbri, Roberto Dallocchio and Paola Carta

Molbank 2025, 2025(2), M2018; https://doi.org/10.3390/M2018 - 6 Jun 2025

Viewed by 129

Abstract

Phenylbutanoids, commonly found in various medicinal plants, have attracted significant attention due to their remarkable biological activities, including antioxidant, anti-inflammatory, and neuroprotective effects, as well as for their versatility as starting materials in organic synthesis. Among phenylbutanoids, phenyl-1,3-butadienes represent a unique class of [...] Read more.

Phenylbutanoids, commonly found in various medicinal plants, have attracted significant attention due to their remarkable biological activities, including antioxidant, anti-inflammatory, and neuroprotective effects, as well as for their versatility as starting materials in organic synthesis. Among phenylbutanoids, phenyl-1,3-butadienes represent a unique class of conjugated dienes, characterized by a phenyl (C₆H₅) group attached to a 1,3-butadiene (-CH=CH-CH=CH₂) backbone. In this study, we synthesized the hydroxylated biphenyl 5,5′-di((E)-buta-1,3-dien-1-yl)-2,2′,3,3′-tetramethoxy-1,1′-biphenyl 1, closely related to its corresponding monomer 2, which is known for its broad range of pharmacological activities. The synthesis was carried out using microwave-assisted technologies. The structure of the synthesized compound was confirmed through elemental analysis, ¹³C-NMR, ¹H-NMR, and ESI-MS spectrometry. Furthermore, we computed this novel compound’s conformational energy profile (CEP), evaluating how its energy varies with changes in the dihedral bond angle. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Graphical abstract

9 pages, 700 KiB

Open AccessCommunication

Novel Acid-Catalyzed Transformation of 1-Benzyl-3-Chloro-5-Hydroxy-4-[(4-Methylphenyl)Sulfanyl]-1,5-Dihydro-2H-Pyrrol-2-One

by Liliya S. Kosolapova, Elena Sh. Saigitbatalova, Liliya Z. Latypova, Marat F. Valiev, Darya P. Gerasimova and Almira R. Kurbangalieva

Molbank 2025, 2025(2), M2017; https://doi.org/10.3390/M2017 - 4 Jun 2025

Viewed by 47

Abstract

Nitrogen-containing heterocycles of 3-pyrrolin-2-one series are widely represented in natural and synthetic compounds, with a broad spectrum of pharmacological activity and considerable potential in medicinal and synthetic organic chemistry. In this communication, we report the previously unknown acid-catalyzed transformation of a N-substituted [...] Read more.

Nitrogen-containing heterocycles of 3-pyrrolin-2-one series are widely represented in natural and synthetic compounds, with a broad spectrum of pharmacological activity and considerable potential in medicinal and synthetic organic chemistry. In this communication, we report the previously unknown acid-catalyzed transformation of a N-substituted derivative of 3-pyrrolin-2-one that generates two types of heterocyclic moieties. The reflux of 1-benzyl-3-chloro-5-hydroxy-4-[(4-methylphenyl)sulfanyl]-1,5-dihydro-2H-pyrrol-2-one in toluene in the presence of catalytic amounts of H₂SO₄ resulted in the formation of a mixture of 1-benzyl-3-[(4-methylphenyl)sulfanyl]-1H-pyrrole-2,5-dione and 1-benzyl-7-methyl-1H-benzo[4,5]thieno[3,2-b]pyrrole-2,3-dione. The structures of four novel nitrogen-containing heterocycles were elucidated through IR, NMR spectroscopy and HRMS spectrometry. A new derivative of the fused tricyclic compounds, possessing benzo[b]thiophene and pyrrole-1,2-dione fragments, was also characterized by single-crystal X-ray diffraction. Full article

(This article belongs to the Collection Heterocycle Reactions)

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8 pages, 1150 KiB

Open AccessCommunication

Structural Characterization of 7-Chloro-4-(4-methyl-1-piperazinyl)quinoline Monohydrate

by Silvia Rizzato and Francesco Marinoni

Molbank 2025, 2025(2), M2016; https://doi.org/10.3390/M2016 - 2 Jun 2025

Viewed by 171

Abstract

The crystal structure of the hydrated form of 7-chloro-4-(4-methyl-1-piperazinyl)quinoline (BPIP) was determined by single-crystal X-ray diffraction analysis. This study revealed a one-dimensional supramolecular network stabilized by hydrogen bonding interactions between BPIP and water molecules. This compound represents one-half of a piperaquine [...] Read more.

The crystal structure of the hydrated form of 7-chloro-4-(4-methyl-1-piperazinyl)quinoline (BPIP) was determined by single-crystal X-ray diffraction analysis. This study revealed a one-dimensional supramolecular network stabilized by hydrogen bonding interactions between BPIP and water molecules. This compound represents one-half of a piperaquine molecule, a member of the 4-aminoquinoline class of antimalarial treatments, currently employed as a partner agent in modern combination therapies. As a simplified structural analog, BPIP can serve as a critical model system for probing the intermolecular interactions, physicochemical properties, and structural behavior of the parent compound. As a result, conducting a thorough solid-state characterization of BPIP is critical for gaining insight into its physical properties and verifying the material’s identity and purity. Full article

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Graphical abstract

9 pages, 1297 KiB

Open AccessCommunication

Near-Infrared Emitting Chiral Tetranuclear Erbium Cluster Containing Soft-Base Bisthiazolate Linkers

by Vasily A. Ilichev, Anton F. Rogozhin, Roman V. Rumyantcev, Georgy K. Fukin and Mikhail N. Bochkarev

Molbank 2025, 2025(2), M2015; https://doi.org/10.3390/M2015 - 29 May 2025

Viewed by 232

Abstract

A tetraerbium cluster containing soft-base dianionic 4,8-difluorobenzo [1,2-d:5,4-d′]bisthiazole-2,6-dithiol (H₂L) ligands, μ-OH, and coordinated 1,2-dimethoxyethane (DME) of the general formula {Er₄(μ-L)₄(μ-OH)₄(DME)₄} (1) was synthesized using [...] Read more.

A tetraerbium cluster containing soft-base dianionic 4,8-difluorobenzo [1,2-d:5,4-d′]bisthiazole-2,6-dithiol (H₂L) ligands, μ-OH, and coordinated 1,2-dimethoxyethane (DME) of the general formula {Er₄(μ-L)₄(μ-OH)₄(DME)₄} (1) was synthesized using a one-pot method. X-ray analysis revealed that 1 is an asymmetrical tetramer in which there are four μ₂-bridging bisthiazole ligands and four μ₂-bridging hydroxide anions per four erbium ions. The molecule of 1 has inherent chirality, and the geometry of intramolecular F…F short contacts implies the formation of a classical halogen bond. Upon excitation by a 375 nm diode laser, compound 1 shows the moderate metal-centered emission of Er³⁺ ions that peaked at 1530 nm. Full article

(This article belongs to the Section Structure Determination)

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8 pages, 1277 KiB

Open AccessShort Note

trans-Dihydroxo[5,10,15,20-tetrakis(3-pyridinium)porphyrinato]tin(IV) Nitrate

by Nirmal Kumar Shee and Hee-Joon Kim

Molbank 2025, 2025(2), M2014; https://doi.org/10.3390/M2014 - 27 May 2025

Viewed by 185

Abstract

The treatment of trans-dihydroxo[5,10,15,20-tetrakis(3-pyridyl)porphyrinato]Sn(IV) or [Sn(OH)₂(TPyP)] with 1% nitric acid in a mixture of water and acetone resulted in the formation of an ionic complex 1 [Sn(OH)₂(TPy^HP)](NO₃)₄. Complex 1 was fully characterized [...] Read more.

The treatment of trans-dihydroxo[5,10,15,20-tetrakis(3-pyridyl)porphyrinato]Sn(IV) or [Sn(OH)₂(TPyP)] with 1% nitric acid in a mixture of water and acetone resulted in the formation of an ionic complex 1 [Sn(OH)₂(TPy^HP)](NO₃)₄. Complex 1 was fully characterized by ¹H NMR spectroscopy, elemental analysis, UV-vis spectroscopy, powder X-ray diffraction, fluorescence spectroscopy, FT-IR spectroscopy, and single-crystal X-ray crystallography. X-ray crystallographic analysis confirmed that each peripheral pyridyl N atom is protonated to form tetra-cationic species {Sn(OH)₂(TPy^HP)}⁴⁺ stabilized by four NO₃⁻ counter anions. Intermolecular hydrogen bonding interaction between axial hydroxo ligands leads to the formation of a 1D porphyrin array. Nitrate anions also involve hydrogen bonding interactions with axial hydroxo ligands and the peripheral pyridinium groups. Full article

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7 pages, 717 KiB

Open AccessShort Note

Diisopropyl (E)-(1-Hydroxy-3-phenylallyl)phosphonate

by Andy I. Coker, Aidan P. McKay, David B. Cordes and Brian A. Chalmers

Molbank 2025, 2025(2), M2013; https://doi.org/10.3390/M2013 - 27 May 2025

Viewed by 202

Abstract

We report the synthesis and the molecular structure as determined by single-crystal X-ray diffraction of diisopropyl (E)-(1-hydroxy-3-phenylallyl)phosphonate. The compound was fully characterised by ¹H, ¹³C, and ³¹P NMR spectroscopy, IR spectroscopy, and Mass Spectrometry. Full article

(This article belongs to the Section Structure Determination)

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8 pages, 479 KiB

Open AccessCommunication

Synthesis of a New Bichalcone via Suzuki–Miyaura Coupling Reaction

by François-Xavier Toublet, Yves Champavier, Aurélie Lévêque, Catherine Fagnère and Christelle Pouget

Molbank 2025, 2025(2), M2012; https://doi.org/10.3390/M2012 - 26 May 2025

Viewed by 225

Abstract

Unlike the wide number of natural biflavonoids, natural bichalcones are a rare and even less studied class. Nevertheless, some of them have proved their interest in the fight against cancer through their cytotoxic activity against human tumor cell lines. The aim of this [...] Read more.

Unlike the wide number of natural biflavonoids, natural bichalcones are a rare and even less studied class. Nevertheless, some of them have proved their interest in the fight against cancer through their cytotoxic activity against human tumor cell lines. The aim of this study was to synthesize a novel bichalcone: 3′,3‴,4,4′,4″,4‴,5′,5‴-octamethoxy-2,3″-bichalcone 1. The most efficient synthetic pathway was the Suzuki–Miyaura reaction between a boronated chalcone and a brominated one. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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8 pages, 374 KiB

Open AccessShort Note

4-(8-Propyl-2,4-dithioxo-1,3-diazaspiro[4.5]decan-3-yl)spiro[1,5-dihydro-1,5-benzodiazepine-2,3′-indoline]-2′-one)

by Dimitar Stoitsov, Marin Marinov, Plamen Penchev and Neyko Stoyanov

Molbank 2025, 2025(2), M2011; https://doi.org/10.3390/M2011 - 23 May 2025

Viewed by 224

Abstract

A number of 1D and 2D NMR techniques, such as ¹H, ¹³C, DEPT 135, ¹H-¹H COSY, HSQC, and HMBC, were utilized for the structure verification of 4-(8-propyl-2,4-dithioxo-1,3-diazaspiro[4.5]decan-3-yl)spiro[1,5-dihydro-1,5-benzodiazepine-2,3′-indoline]-2′-one). The NMR spectra provided evidence for the tautomeric conversion of the [...] Read more.

A number of 1D and 2D NMR techniques, such as ¹H, ¹³C, DEPT 135, ¹H-¹H COSY, HSQC, and HMBC, were utilized for the structure verification of 4-(8-propyl-2,4-dithioxo-1,3-diazaspiro[4.5]decan-3-yl)spiro[1,5-dihydro-1,5-benzodiazepine-2,3′-indoline]-2′-one). The NMR spectra provided evidence for the tautomeric conversion of the compound. The completely assigned NMR data was supported additionally by ATR. Full article

(This article belongs to the Section Structure Determination)

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12 pages, 1408 KiB

Open AccessCommunication

Synthesis of Mesoionic 1,3,4-Thiadiazole-2-Thiolates

by Sean Ray Kahnert and Andreas Schmidt

Molbank 2025, 2025(2), M2010; https://doi.org/10.3390/M2010 - 22 May 2025

Viewed by 226

Abstract

A reliable synthesis of C5-unsubstituted 1,3,4-thiadiazole-2-thiolates is described that avoids potentially explosive or laborious steps. This work presents a reliable method for preparing the starting material dithioformate from carbon disulfide and potassium or sodium tri-sec-butylhydroborates for the preparation of the mesoionic [...] Read more.

A reliable synthesis of C5-unsubstituted 1,3,4-thiadiazole-2-thiolates is described that avoids potentially explosive or laborious steps. This work presents a reliable method for preparing the starting material dithioformate from carbon disulfide and potassium or sodium tri-sec-butylhydroborates for the preparation of the mesoionic title compounds with potassium hydrazinecarbodithioates. New 1,3,4-thiadiazole-2-thiolates are presented, and missing structural analysis data of known derivatives are added (1D- and 2D-NMR, HR-ESI-MS, IR). Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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7 pages, 549 KiB

Open AccessCommunication

An Alternative Method for Preparing Methyl 2-Ferrocenyl-2-oxo-acetate

by Pascal Pigeon and Hugo Hapel

Molbank 2025, 2025(2), M2009; https://doi.org/10.3390/M2009 - 21 May 2025

Viewed by 118

Abstract

Because of the continuous interest in ferrocene chemistry, there is a sustained demand for various ferrocenic building blocks, especially small molecules with useful chemical functional groups, sometimes containing multiple groups. Our interest in ferrocene ketoesters (ω-ferrocenyl-ω-ketoesters) was motivated by the synthesis of esters [...] Read more.

Because of the continuous interest in ferrocene chemistry, there is a sustained demand for various ferrocenic building blocks, especially small molecules with useful chemical functional groups, sometimes containing multiple groups. Our interest in ferrocene ketoesters (ω-ferrocenyl-ω-ketoesters) was motivated by the synthesis of esters and subsequently alcohols of ferrociphenols. However, from a bibliographic survey, only one publication dated from 1964 reports the two-step synthesis (six-step synthesis from ferrocene) of methyl 2-ferrocenyl-2-oxoacetate, the simplest member of this family of compounds, with no further developments since. We hypothesized that a simpler method might exist, such as the Friedel–Crafts method. By focusing on our experiments to use aluminum trichloride as the catalyst, we managed to achieve the synthesis of FcCOCOOMe in a single step, albeit with a very low yield, regardless of reaction time, temperature, amount of aluminum chloride and reagents concentration. Nevertheless, considering the time saved, simplicity, and the use of less hazardous and less expensive reagents, this method offers certain advantages for synthesizing this building block. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Graphical abstract

8 pages, 4572 KiB

Open AccessCommunication

Crystal Structure and Hirshfeld Surface Analysis of Hexakis(acetoxymethyl)benzene

by Manuel Stapf, Wilhelm Seichter and Monika Mazik

Molbank 2025, 2025(2), M2008; https://doi.org/10.3390/M2008 - 16 May 2025

Viewed by 181

Abstract

Representatives of the hexasubstituted benzene derivatives, also known as hexa-hosts, have been the subject of extensive studies in solution and in the solid state, including the investigation of their ability to act as artificial receptors for various substrates, as well as detailed conformational [...] Read more.

Representatives of the hexasubstituted benzene derivatives, also known as hexa-hosts, have been the subject of extensive studies in solution and in the solid state, including the investigation of their ability to act as artificial receptors for various substrates, as well as detailed conformational analyses. In this paper, we describe the X-ray crystal structure of hexakis(acetoxymethyl)benzene (1), a member of the above class of compounds. The molecules of 1 adopt an aaabbb conformation, in which three side-arms point to the same face of the central benzene ring, while the other three point in the opposite direction. As the compound lacks strong hydrogen bond donors, C–H···O hydrogen bonds connect the molecules to a three-dimensional supramolecular network. According to the Hirshfeld surface analysis, the H∙∙∙O/O∙∙∙H interactions represent the major contribution of the molecular Hirshfeld surface. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

7 pages, 2295 KiB

Open AccessShort Note

2′,7′-Dimethyl-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one

by Brian A. Chalmers, Aidan P. McKay, David B. Cordes, Iain L. J. Patterson, Nadiia Vladymyrova and Iain A. Smellie

Molbank 2025, 2025(2), M2007; https://doi.org/10.3390/M2007 - 14 May 2025

Viewed by 179

Abstract

A synthetic route to 2′,7′-dimethyl-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one has been described using methanesulfonic acid in place of reagents described in protocols from the early 20th century. A full NMR assignment has been made and X-ray crystallography has been used to characterise the title compound [...] Read more.

A synthetic route to 2′,7′-dimethyl-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one has been described using methanesulfonic acid in place of reagents described in protocols from the early 20th century. A full NMR assignment has been made and X-ray crystallography has been used to characterise the title compound for the first time. Full article

(This article belongs to the Section Structure Determination)

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8 pages, 17118 KiB

Open AccessShort Note

(Z)-4-(Azulen-1-ylmethylene)-2-phenyloxazol-5(4H)-one

by Mihaela Cristea, Alexandru C. Razus, Sergiu Shova, Marcel-Mirel Popa, Mihai Răducă and Florea Dumitrascu

Molbank 2025, 2025(2), M2006; https://doi.org/10.3390/M2006 - 8 May 2025

Viewed by 280

Abstract

The title compound, i.e., (Z)-4-(azulen-1-ylmethylene)-2-phenyloxazol-5(4H)-one (3), has previously been synthesized in a good yield (56%) using the Erlenmeyer–Plöchl procedure. The crystal structure of 3 is described herein along with the results of a Hirshfeld surface analysis. Crystals of [...] Read more.

The title compound, i.e., (Z)-4-(azulen-1-ylmethylene)-2-phenyloxazol-5(4H)-one (3), has previously been synthesized in a good yield (56%) using the Erlenmeyer–Plöchl procedure. The crystal structure of 3 is described herein along with the results of a Hirshfeld surface analysis. Crystals of compound 3 were obtained through the slow evaporation of a mixture of petroleum ether/dichloromethane = 1:1 (vol.) at room temperature. This compound has a monoclinic system: a P2₁/n space group at room temperature. Its crystal packing is driven by π-π interactions between neighboring molecules in the range of 3.60–3.71 Å and by hydrogen bonds (D-H···A = 2.58 Å). Full article

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Graphical abstract

9 pages, 2127 KiB

Open AccessCommunication

Synthesis of Vanillic Acid—Meldrum’s Acid Conjugate

by Laima Bērziņa and Inese Mieriņa

Molbank 2025, 2025(2), M2005; https://doi.org/10.3390/M2005 - 7 May 2025

Viewed by 205

Abstract

A vanillic acid—Meldrum’s acid conjugate with a 1,2,3-triazole linker is synthesized. The reaction sequence foresees the Huisgen reaction and the Knoevenagel condensation as the key-steps. Full article

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Graphical abstract

5 pages, 486 KiB

Open AccessCommunication

Synthesis and Characterization of New Monosubstituted Pillar[5]arene with Terminal Carboxyl Group

by Luidmila Yakimova, Darya Filimonova, Anastasia Nazarova and Ivan Stoikov

Molbank 2025, 2025(2), M2004; https://doi.org/10.3390/M2004 - 6 May 2025

Viewed by 212

Abstract

The subject of this article is a new monosubstituted pillar[5]arene with a terminal carboxylic group. Previously, it was shown that monosubstituted pillar[5]arene forms solid lipid nanoparticles with various morphologies depending on the nature of the terminal group. The present work is devoted to [...] Read more.

The subject of this article is a new monosubstituted pillar[5]arene with a terminal carboxylic group. Previously, it was shown that monosubstituted pillar[5]arene forms solid lipid nanoparticles with various morphologies depending on the nature of the terminal group. The present work is devoted to the synthesis of monosubstituted pillar[5]arene with an anionic carboxylic group for the further creation of drug–carrier systems based on them. The chemical structure of the product obtained was established based on ¹H and ¹³C NMR, IR spectroscopy, MALDI TOF mass spectrometry, and elemental analysis. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Scheme 1

6 pages, 1653 KiB

Open AccessCommunication

Stereoselective Preparation of (4S)-1-Methyl-4-propyl-L-proline Commencing from (cis)-4-Hydroxy-L-proline

by Gour Hari Mandal, Shifali Choudhary, Steven P. Kelley and Shyam Sathyamoorthi

Molbank 2025, 2025(2), M2003; https://doi.org/10.3390/M2003 - 5 May 2025

Viewed by 390

Abstract

We present a recipe for the stereoselective conversion of commercial (cis)-4-hydroxy-L-proline into (4S)-1-methyl-4-propyl-L-proline, an analog of the amino acid fragment found in the clinically used antibacterial antibiotic lincomycin. The single-crystal X-ray diffraction analysis of the final target’s hydrochloride salt [...] Read more.

We present a recipe for the stereoselective conversion of commercial (cis)-4-hydroxy-L-proline into (4S)-1-methyl-4-propyl-L-proline, an analog of the amino acid fragment found in the clinically used antibacterial antibiotic lincomycin. The single-crystal X-ray diffraction analysis of the final target’s hydrochloride salt confirms its identity and absolute stereochemistry. Full article

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Graphical abstract

9 pages, 1682 KiB

Open AccessCommunication

Synthesis of Dimethyl (Z)-((3-oxoindolin-2-ylidene) (aryl)methyl)phosphonates Through Tandem Cadogan and Arbuzov Reactions

by Nicolai A. Aksenov, Dmitrii A. Aksenov, Daniil D. Ganusenko, Alexander E. Kurlikov, Alexander P. Barbolin, Polina S. Karaseva and Alexander V. Aksenov

Molbank 2025, 2025(2), M2002; https://doi.org/10.3390/M2002 - 5 May 2025

Viewed by 324

Abstract

A novel method employing a tandem Cadogan and Arbuzov reaction sequence has been developed, providing access to a series of previously unreported dimethyl (Z)-((3-oxoindolin-2-ylidene)(aryl)methyl)phosphonates. Restricted rotation of the aryl substituent, particularly in the presence of ortho substituents, gives axial chirality to these compounds. [...] Read more.

A novel method employing a tandem Cadogan and Arbuzov reaction sequence has been developed, providing access to a series of previously unreported dimethyl (Z)-((3-oxoindolin-2-ylidene)(aryl)methyl)phosphonates. Restricted rotation of the aryl substituent, particularly in the presence of ortho substituents, gives axial chirality to these compounds. Full article

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5 pages, 1105 KiB

Open AccessShort Note

6,7,8,9-Tetrafluoro-11H-indeno[1,2-b]quinoxalin-11-one

by Anastasia R. Kovrizhina, Irina Yu. Bagryanskaya, Andrey V. Zibarev and Andrei I. Khlebnikov

Molbank 2025, 2025(2), M2001; https://doi.org/10.3390/M2001 - 28 Apr 2025

Viewed by 293

Abstract

Fluorinated aza-heterocycles are important in organic and medicinal chemistry. Currently, a quarter of the drugs on the global market contain fluorine. We report the synthesis of the title compound and its single-crystal XRD structure. Full article

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5 pages, 350 KiB

Open AccessShort Note

5,7-Diiodoquinolin-8-yl (E)-3-(3,4-dihydroxyphenyl)acrylate

by Marcin Cybulski, Michał Zieliński, Marek Kubiszewski and Olga Michalak

Molbank 2025, 2025(2), M2000; https://doi.org/10.3390/M2000 - 28 Apr 2025

Viewed by 230

Abstract

We report the synthesis of 5,7-diiodoquinolin-8-yl ester of caffeic acid and its O,O-diallyl-protected analogue. The compounds from the hybrid class were fully characterised using NMR spectroscopy and high-resolution mass spectrometry. Full article

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Scheme 1

11 pages, 1782 KiB

Open AccessCommunication

1-(Pyrrolidin-1-yl)naphtho[1,2-d]isoxazole

by Ioannis E. Gerontitis, Abdul kadar Shaikh, Dimitrios Alivertis, Panteleimon G. Takis, Anastassios N. Troganis, Petros G. Tsoungas and George Varvounis

Molbank 2025, 2025(2), M1999; https://doi.org/10.3390/M1999 - 27 Apr 2025

Viewed by 408

Abstract

In this study, we examined the oxidation of (E)-2-hydroxy-1-naphthaldehyde oxime with lead tetraacetate in tetrahydrofuran that produced novel (E)-7a,8,9,10-tetrahydro-12H-naphtho[1,2-e]pyrrolo[2,1-b][1,3]oxazin-12-one oxime and 1-(pyrrolidin-1-yl)naphtho[1,2-d]isoxazole and known 7a,8,9,10-tetrahydro-12H-naphtho[1,2-e]pyrrolo-[2,1-b][1,3]oxazin-12-one [...] Read more.

In this study, we examined the oxidation of (E)-2-hydroxy-1-naphthaldehyde oxime with lead tetraacetate in tetrahydrofuran that produced novel (E)-7a,8,9,10-tetrahydro-12H-naphtho[1,2-e]pyrrolo[2,1-b][1,3]oxazin-12-one oxime and 1-(pyrrolidin-1-yl)naphtho[1,2-d]isoxazole and known 7a,8,9,10-tetrahydro-12H-naphtho[1,2-e]pyrrolo-[2,1-b][1,3]oxazin-12-one in 15, 18, and 10% yields, respectively. The oxime is partially hydrolyzed to its corresponding ketone. Modifying the oxidants and reaction conditions did not improve the product yields. Based on previous studies in our laboratory, we proposed that the reactions proceed via the formation of an o-naphthoquinone nitrosomethide intermediate; 1D and 2D NMR, HRMS, IR, and UV-VIS spectra provided information that supported the structure of the products. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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8 pages, 644 KiB

Open AccessShort Note

4,4′-(Anthracene-9,10-diylbis(ethyne-2,1-diyl))bis(1-benzyl-1-pyridinium) Bromide

by Valentina Novelli, Andrea D’Annibale, Fabrizio Casano, Alessandro Latini and Lorenza Romagnoli

Molbank 2025, 2025(2), M1998; https://doi.org/10.3390/M1998 - 27 Apr 2025

Viewed by 313

Abstract

Viologens, i.e., quaternary 4,4′-bipyridinum salts, are a well-known class of functional organic compounds that have attracted in the past few decades a great deal of attention for their peculiar chemical and electrochemical properties and have therefore found numerous applications ranging from herbicides to [...] Read more.

Viologens, i.e., quaternary 4,4′-bipyridinum salts, are a well-known class of functional organic compounds that have attracted in the past few decades a great deal of attention for their peculiar chemical and electrochemical properties and have therefore found numerous applications ranging from herbicides to electrochromic devices. In this paper, the synthesis and characterization of a novel viologen derivative are described. In the reported compound, the pyridinium nitrogen atoms have been quaternarized with the benzyl group and an additional unsaturated moiety, namely a 9,10-diethynylanthracene core, has been inserted between the charged pyridinium rings to extend the conjugation. Characterization by means of absorbance and diffuse reflectance UV–visible spectroscopy suggested intriguing optical and electronic properties, making this extended viologen a potential candidate for different optoelectronic applications. Full article

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7 pages, 958 KiB

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(E)-4,2′,4′-Trimethoxychalcone (Z)-N-Tosyl Hydrazone

by Sonia Berenguel Gómez, Irene Moreno-Gutiérrez, Manuel Muñoz-Dorado, Míriam Álvarez-Corral and Ignacio Rodríguez-García

Molbank 2025, 2025(2), M1997; https://doi.org/10.3390/M1997 - 27 Apr 2025

Viewed by 296

Abstract

The synthesis and structural characterization of (E)-4,2′,4′-trimethoxychalcone (Z)-N-tosyl hydrazone, a conjugated tosylhydrazone derivative, is described. The compound was obtained via the condensation of (E)-1-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one with p-toluenesulfonylhydrazide in methanol under mild conditions, yielding a yellow [...] Read more.

The synthesis and structural characterization of (E)-4,2′,4′-trimethoxychalcone (Z)-N-tosyl hydrazone, a conjugated tosylhydrazone derivative, is described. The compound was obtained via the condensation of (E)-1-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one with p-toluenesulfonylhydrazide in methanol under mild conditions, yielding a yellow solid in a 66% yield. The structure of the product was confirmed through ¹H NMR, ¹³C NMR, IR spectroscopy, mass spectrometry, and single-crystal X-ray diffraction analysis, which revealed a non-planar molecular conformation and a Z configuration for the C=N double bond. This work is part of our ongoing research on carbene-mediated transformations. Full article

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6 pages, 1285 KiB

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2,2′-((5,5′,6,6′-Tetramethoxy-[1,1′-biphenyl]-3,3′-diyl)bis(methanylylidene))dimalononitrile

by David Gendron and Josée Labrecque

Molbank 2025, 2025(2), M1996; https://doi.org/10.3390/M1996 - 24 Apr 2025

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Abstract

This report discusses the synthesis of a biosourced divanillin derivative obtained by Knoevenagel condensation. The compound was fully characterized by proton (¹H), carbon (¹³C), heteronuclear single quantum coherence (HSQC), homonuclear correlation spectroscopy (COSY), and heteronuclear multiple bond correlation (HMBC) [...] Read more.

This report discusses the synthesis of a biosourced divanillin derivative obtained by Knoevenagel condensation. The compound was fully characterized by proton (¹H), carbon (¹³C), heteronuclear single quantum coherence (HSQC), homonuclear correlation spectroscopy (COSY), and heteronuclear multiple bond correlation (HMBC) NMR, as well as high-resolution mass spectroscopy (HRMS). We also investigated the optical properties through UV-visible spectroscopy and Fourier-transform infrared (FTIR) spectroscopy. At last, the thermal properties of this divanillin derivative were evaluated by thermogravimetric analysis (TGA) as well as differential scanning calorimetry (DSC). Full article

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6 pages, 1255 KiB

Open AccessShort Note

(3a,8b)-5-Acetyl-3a-fluoro-6,8-dihydroxy-7,8b-dimethyl-3,3a-dihydrofuro[3,2-b]benzofuran-2(8bH)-one

by Aleksandr S. Filimonov, Stepan P. Zernov, Olga A. Luzina and Nariman F. Salakhutdinov

Molbank 2025, 2025(2), M1995; https://doi.org/10.3390/M1995 - 24 Apr 2025

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Abstract

Usnetic acid is a dibenzofuran-2-ylacetic acid that can be obtained by alkaline degradation of a secondary lichen metabolite—usnic acid. In the present paper, the product of the reaction of usnetic acid with a mild fluorinating agent, Selectfluor^®, was obtained. The structure [...] Read more.

Usnetic acid is a dibenzofuran-2-ylacetic acid that can be obtained by alkaline degradation of a secondary lichen metabolite—usnic acid. In the present paper, the product of the reaction of usnetic acid with a mild fluorinating agent, Selectfluor^®, was obtained. The structure of the product was proved by a set of physical methods, including ¹H, ¹³C, ¹⁹F NMR, HMBC, HSQC, HRMS and IR spectroscopy. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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7 pages, 603 KiB

Open AccessShort Note

6-(7,8-Dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)hexyl 5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate

by Simona Marincean, Diana Nichols, Rachael Schulz, Travis Branscum and Marilee Benore

Molbank 2025, 2025(2), M1994; https://doi.org/10.3390/M1994 - 23 Apr 2025

Viewed by 282

Abstract

Herein we report the synthesis of 6-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)hexyl 5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate. The compound was fully characterized by melting point, ¹H-, ¹³C-NMR spectroscopy, IR spectroscopy, UV-VIS spectroscopy, mass spectrometry, and elemental analysis. The obtained data confirmed the successful synthesis and structure of the novel molecule. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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4 pages, 482 KiB

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N-(2,2-Diphenylethyl)furan-2-carboxamide

by Iliyan Ivanov, Diyana Dimitrova and Stanimir Manolov

Molbank 2025, 2025(2), M1993; https://doi.org/10.3390/M1993 - 16 Apr 2025

Viewed by 784

Abstract

We report the synthesis of N-(2,2-diphenylethyl)furan-2-carboxamide. The compound was fully characterized by melting point determination, ¹H and ¹³C NMR spectroscopy, infrared spectroscopy, and mass spectrometry. The combined analytical data confirm both the successful synthesis and the structural integrity of the target molecule. Full article

(This article belongs to the Section Structure Determination)

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5 pages, 932 KiB

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N-(3-(tert-Butyl)-1-methyl-1H-pyrazol-5-yl)-4-methyl-N-tosylbenzenesulfonamide

by Diana Becerra and Juan-Carlos Castillo

Molbank 2025, 2025(2), M1992; https://doi.org/10.3390/M1992 - 15 Apr 2025

Viewed by 829

Abstract

N-(3-(tert-Butyl)-1-methyl-1H-pyrazol-5-yl)-4-methyl-N-tosylbenzenesulfonamide was efficiently synthesized in good yield through a triethylamine-mediated sulfonamidation reaction of 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine with 4-methylbenzenesulfonyl chloride in acetonitrile at room temperature. The pyrazole-based benzenesulfonamide was fully characterized using FT-IR, NMR, and HMRS techniques. Full article

(This article belongs to the Collection Heterocycle Reactions)

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6 pages, 1615 KiB

Open AccessShort Note

4-[2-(Chlorodiphenylstannyl)phenyl]-4-hydroxybutan-2-one

by Adrian-Alexandru Someșan and Richard A. Varga

Molbank 2025, 2025(2), M1991; https://doi.org/10.3390/M1991 - 9 Apr 2025

Viewed by 329

Abstract

An aldol condensation reaction between [2-(O=CH)C₆H₄]SnPh₂Cl and acetone gave [2-{CH₃C(=O)CH₂(OH)CH}C₆H₄]SnPh₂Cl (1). The compound was characterized in a solution using multinuclear NMR spectroscopy and HR-MS spectrometry [...] Read more.

An aldol condensation reaction between [2-(O=CH)C₆H₄]SnPh₂Cl and acetone gave [2-{CH₃C(=O)CH₂(OH)CH}C₆H₄]SnPh₂Cl (1). The compound was characterized in a solution using multinuclear NMR spectroscopy and HR-MS spectrometry and in a solid state using IR spectroscopy and single-crystal X-ray diffraction. The molecular structure revealed the presence of both enantiomers in the crystal. Full article

(This article belongs to the Section Structure Determination)

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Molbank, Volume 2025, Issue 2 (June 2025) – 38 articles

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