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Molbank
Volume 2025
Issue 2
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Molbank, Volume 2025, Issue 2 (June 2025) – 42 articles

Cover Story (view full-size image): The novel C2-symmetric biphenyl derivative, 5,5′-di((E)-buta-1,3-dien-1-yl)-2,2′,3,3′-tetramethoxy-1,1′-biphenyl (1), was synthesized via a microwave-assisted protocol starting from a vanillin-derived precursor. The reaction proceeded with high stereoselectivity, yielding the target compound exclusively in the (E,E) configuration. This molecule displays significant stereochemical complexity. The presence of a C2 symmetry axis, combined with its distinct conformational and configurational features, contributes to its unique structural profile. These characteristics are likely to impact its potential utility in stereoselective synthesis or molecular recognition processes. A comprehensive structural and spectroscopic characterization of compound 1 is presented, emphasizing its novel features and the efficiency of the synthetic strategy. View this paper
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8 pages, 882 KiB  
Short Note
bis(2-Phenylpyridinato)-[4,4′-bis(iodoethynyl)-2,2′-bipyridine]-iridium(III) Hexafluorophosphate
by Patrick Endres, Nishi Singh, Andreas Winter, Helmar Görls and Ulrich S. Schubert
Molbank 2025, 2025(2), M2024; https://doi.org/10.3390/M2024 - 18 Jun 2025
Viewed by 186
Abstract
This work presents the synthesis and structural characterization of a novel type of biscyclometalated Ir(III) complex, which is equipped with two iodoethynyl moieties on its 2,2′-bipyridine (bpy) ligand. Iodoethynyl moieties represent prominent donor systems for the formation of supramolecular structures via halogen bonding [...] Read more.
This work presents the synthesis and structural characterization of a novel type of biscyclometalated Ir(III) complex, which is equipped with two iodoethynyl moieties on its 2,2′-bipyridine (bpy) ligand. Iodoethynyl moieties represent prominent donor systems for the formation of supramolecular structures via halogen bonding (X-bonding). The synthesis of bis(2-phenylpyridinato)-[4,4′-bis(iodoethynyl)-2,2′-bipyridine]iridium(III) hexafluorophosphate, (2)(PF6), is straightforward and involves post-complexation iodination, thus expanding the already rich toolbox for performing “chemistry on the complex”. The formation of the iodoethynyl moieties was unequivocally proven by 1H-NMR spectroscopy, ESI-TOF mass spectrometry, and single-crystal XRD analysis. Full article
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4 pages, 560 KiB  
Short Note
(Z)-2-(Bromomethyl)-3-(hydroxymethylene)-7-methoxy-5-methyl-2-(tribromomethyl)-4-chromanone
by Chein-Chung Lee and Yen-Ku Wu
Molbank 2025, 2025(2), M2023; https://doi.org/10.3390/M2023 - 16 Jun 2025
Viewed by 184
Abstract
An attempt to achieve the deprotonative bromination of a 2-methyl-3-formyl-chromenone with tetrabromomethane led to an unexpected bromo-tribromomethylation product. We report the synthesis and characterization of the title compound. Full article
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9 pages, 2176 KiB  
Short Note
4-Methyl-N-(1-benzyl)-N’-(1-benzylidene)benzenesulfonohydrazide
by Leticia Almazán-Sánchez, Marco A. García-Eleno, Diego Martínez-Otero and Erick Cuevas-Yañez
Molbank 2025, 2025(2), M2022; https://doi.org/10.3390/M2022 - 13 Jun 2025
Viewed by 212
Abstract
4-Methyl-N-(1-benzyl)-N’-(1-benzylidene)benzenesulfonohydrazide is formed through a direct, solventless reaction between benzaldehyde tosylhydrazone and potassium carbonate, which is carried out using an eco-friendly grinding method. The NMR spectra of the compound are here described. The structure was unequivocally determined by X-ray [...] Read more.
4-Methyl-N-(1-benzyl)-N’-(1-benzylidene)benzenesulfonohydrazide is formed through a direct, solventless reaction between benzaldehyde tosylhydrazone and potassium carbonate, which is carried out using an eco-friendly grinding method. The NMR spectra of the compound are here described. The structure was unequivocally determined by X-ray analysis. As suggested by Hirshfeld surface analysis, the predominant intermolecular H-O interactions in this molecule are involved in crystal packing. Full article
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9 pages, 516 KiB  
Short Note
4,4-Dichloro-1,3-dithietane-2-one
by Tracy R. Thompson, William W. Brennessel, Erik S. Goebel, Matthew J. Turcotte and George Barany
Molbank 2025, 2025(2), M2021; https://doi.org/10.3390/M2021 - 13 Jun 2025
Viewed by 436
Abstract
The title compound, 4,4-dichloro-1,3-dithietane-2-one, was encountered when opening a commercial capped amber bottle labeled “thiophosgene” that had been stored in a cold room (4 °C) for decades without any special precautions. Treating it as an unknown, the structure was established by single crystal [...] Read more.
The title compound, 4,4-dichloro-1,3-dithietane-2-one, was encountered when opening a commercial capped amber bottle labeled “thiophosgene” that had been stored in a cold room (4 °C) for decades without any special precautions. Treating it as an unknown, the structure was established by single crystal X-ray analysis, and confirmed by 13C NMR, FTIR, melting behavior, and elemental analysis; its behavior under several mass spectrometric conditions was also examined. The dithietane appears to be a spontaneously formed cyclodimer of thiophosgene in which exactly one (not zero, not both) of the dichloromethylene moieties has been hydrolyzed to a carbonyl function. The relative long-term stability of the hydrolyzed dimer, along with a pathway back to thiophosgene, suggests that it might serve as a storage vehicle for toxic thiophosgene. Furthermore, as noted elsewhere, the title compound reacts with nucleophiles under mild aqueous conditions, suggesting that it may be a useful probe in chemical biology. Full article
(This article belongs to the Collection Molecules from Side Reactions)
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11 pages, 3378 KiB  
Communication
[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 - 9 Jun 2025
Viewed by 424
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 P1¯ 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  
Communication
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 502
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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9 pages, 2019 KiB  
Short 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 317
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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9 pages, 700 KiB  
Communication
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 436
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  
Communication
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 387
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  
Communication
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 727
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  
Short 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 449
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(TPyHP)](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(TPyHP)](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(TPyHP)}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  
Short 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 469
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  
Communication
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 420
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  
Short 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 406
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  
Communication
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 378
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  
Communication
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 269
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  
Communication
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 489
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  
Short 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 358
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  
Short 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 400
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  
Communication
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 403
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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5 pages, 486 KiB  
Communication
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 370
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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6 pages, 1653 KiB  
Communication
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 545
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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9 pages, 1682 KiB  
Communication
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 584
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  
Short 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 356
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  
Short 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 285
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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11 pages, 1782 KiB  
Communication
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 569
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  
Short 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 388
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  
Short Note
(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 411
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  
Short Note
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
Viewed by 283
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  
Short 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
Viewed by 292
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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