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Volume 2025
Issue 2
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Molbank, Volume 2025, Issue 2 (June 2025) – 19 articles

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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 (registering DOI) - 28 Apr 2025
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 (registering DOI) - 28 Apr 2025
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, 1146 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 (registering DOI) - 27 Apr 2025
Viewed by 48
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 (registering DOI) - 27 Apr 2025
Viewed by 113
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 (registering DOI) - 27 Apr 2025
Viewed by 104
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 (registering DOI) - 24 Apr 2025
Viewed by 94
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 101
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  
Short 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 103
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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Graphical abstract

4 pages, 482 KiB  
Short Note
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 147
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  
Short Note
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 170
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  
Short 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 212
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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Graphical abstract

6 pages, 1256 KiB  
Communication
Synthesis and Intramolecular Regioselective Cyclization of 2-Cyano-3,10-dioxo-1,10-seco-1,25-dinorlupan-28-yl Benzoate
by Irina Tolmacheva, Mikhail Nazarov and Victoria Grishko
Molbank 2025, 2025(2), M1990; https://doi.org/10.3390/M1990 - 7 Apr 2025
Viewed by 161
Abstract
The paper describes the synthesis of a new 1,10-seco-triterpenoid with a 2-cyano-3,10-diketone fragment and its further regioselective cyclization under acidic and basic conditions with the formation of 2S-cyanopyran-3-one derivative or A-pentacyclic alkene β-ketonitrile, respectively. Full article
(This article belongs to the Section Natural Product Chemistry)
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5 pages, 335 KiB  
Communication
Synthesis of a 2-(2-Trifluoroethoxyphenyl)oxazoline
by R. Alan Aitken and Andrew D. Harper
Molbank 2025, 2025(2), M1989; https://doi.org/10.3390/M1989 - 2 Apr 2025
Viewed by 213
Abstract
The title compound has been prepared in four steps starting from ethyl 2-fluorobenzoate. The final product as well as the intermediates are fully characterised by spectroscopic methods with the 1H and 13C NMR spectra, featuring coupling to 19F being particularly informative. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Scheme 1

11 pages, 1910 KiB  
Communication
Synthesis and Characterization of cis-/trans-(±)-3-Alkyl-3,4-dihydro-6,7-dimethoxy-1-oxo-1H-isochromene-4-carboxylic Acids
by Savina Stoyanova and Milen G. Bogdanov
Molbank 2025, 2025(2), M1988; https://doi.org/10.3390/M1988 - 1 Apr 2025
Viewed by 187
Abstract
A series of new 3-alkyl substituted cis- and trans-(±)-3,4-dihydro-6,7-dimethoxy-1-oxo-1H-isochromene-4-carboxylic acids (cis-/trans-1–3) was synthesized through the reaction of 6,7-dimethoxyhomophthalic anhydride with aliphatic aldehydes of varying chain lengths. Their structure and configuration were [...] Read more.
A series of new 3-alkyl substituted cis- and trans-(±)-3,4-dihydro-6,7-dimethoxy-1-oxo-1H-isochromene-4-carboxylic acids (cis-/trans-1–3) was synthesized through the reaction of 6,7-dimethoxyhomophthalic anhydride with aliphatic aldehydes of varying chain lengths. Their structure and configuration were elucidated using spectral methods, including 1H, 13C, DEPT-135 NMR, FTIR, UV-Vis, and HRMS analyses. A deductive conformational analysis was performed for determining the preferred conformations in solution and to explain the observed vicinal coupling constants. Full article
(This article belongs to the Section Structure Determination)
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9 pages, 761 KiB  
Communication
2D Coordination Polymer [Fe(piv)2(dab)2]n
by Vladimir A. Bushuev, Dmitriy S. Yambulatov, Stanislav A. Nikolaevskii, Mikhail A. Kiskin and Igor L. Eremenko
Molbank 2025, 2025(2), M1987; https://doi.org/10.3390/M1987 - 31 Mar 2025
Viewed by 277
Abstract
The interaction of preorganized iron(II) pivalate complexes with aromatic N-donor ligand (pyridine (py) or 2,2′-bipyridine (bpy)) and 1,4-diaminobutane (dab, putrescine) in anhydrous acetonitrile yielded a new 2D coordination polymer [Fe(piv)2(dab)2]n (1, piv = Me3CCO [...] Read more.
The interaction of preorganized iron(II) pivalate complexes with aromatic N-donor ligand (pyridine (py) or 2,2′-bipyridine (bpy)) and 1,4-diaminobutane (dab, putrescine) in anhydrous acetonitrile yielded a new 2D coordination polymer [Fe(piv)2(dab)2]n (1, piv = Me3CCO2–). The molecular structure of 1 in crystal was determined by single-crystal X-ray diffraction analysis and ATR-FTIR spectroscopy. Full article
(This article belongs to the Section Structure Determination)
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5 pages, 2383 KiB  
Short Note
(E,E)-1,5-Diethoxy-1,5-diphenylpenta-1,4-dien-3-one
by R. Alan Aitken, David B. Cordes, Verity Kennett and Aidan P. McKay
Molbank 2025, 2025(2), M1986; https://doi.org/10.3390/M1986 - 28 Mar 2025
Viewed by 285
Abstract
The title compound has been fully characterised for the first time. Fully assigned 1H and 13C NMR spectra and the X-ray structure are presented. Full article
(This article belongs to the Section Structure Determination)
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Graphical abstract

11 pages, 2423 KiB  
Communication
Synthesis of N,N-Dimethylaminopropyl Derivative of A Blood Sugar Antigen
by Elena Di Marzo, Luigi Lay and Giuseppe D’Orazio
Molbank 2025, 2025(2), M1985; https://doi.org/10.3390/M1985 - 27 Mar 2025
Viewed by 260
Abstract
Gold nanoparticles (AuNPs) are a promising tool for drug delivery due to their unique chemical properties that make them biocompatible and easy to functionalize. However, when AuNPs are introduced into biological systems, they are coated by the so-called protein corona (PC), which affects [...] Read more.
Gold nanoparticles (AuNPs) are a promising tool for drug delivery due to their unique chemical properties that make them biocompatible and easy to functionalize. However, when AuNPs are introduced into biological systems, they are coated by the so-called protein corona (PC), which affects their biodistribution and limits their therapeutic efficacy. The functionalization of AuNPs with endogenous carbohydrates can be a possible strategy to reduce immune recognition, thus enhancing their biocompatibility and circulation time. Suitable candidates for this approach are the ABO blood sugar antigens, di- and tri-saccharides that represent the terminal portion of some glycolipids and glycoproteins present on the surface of human red blood cells and other tissues. In this work, we illustrate the synthesis of trisaccharide antigen A derivative, whose last step is worthy of investigation. During the final hydrogenolysis reaction, intended to remove protecting groups, an unexpected side reaction occurred, the isolated product bearing an N,N-dimethyl moiety on the anomeric propyl linker. This side reaction might be ascribed to the in situ formation of formaldehyde and successive imine formation and reduction. The obtained compound can be used as a monomeric control compound in biochemical and structural biology studies involving ABO blood sugar antigens. Full article
(This article belongs to the Collection Molecules from Side Reactions)
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6 pages, 7999 KiB  
Short Note
tert-Butyl (6-(3-(3-Fluorophenyl)ureido)hexyl)carbamate
by Daria Zapravdina, Konstantin Eremeev, Ilya A. Yakushev, Anna Maksimova, Jourdan Bynerie and Vladimir Burmistrov
Molbank 2025, 2025(2), M1984; https://doi.org/10.3390/M1984 - 26 Mar 2025
Viewed by 229
Abstract
The title compound, tert-butyl (6-(3-(3-fluorophenyl)ureido)hexyl)carbamate, was synthesized and characterized by NMR, MS, elemental analysis, and single-crystal X-ray diffraction. This urea can serve as a framework for the preparation of unsymmetrical diureas or compounds containing both urea and thiourea groups. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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4 pages, 502 KiB  
Short Note
Benzyl 2-Phenyl-1H-pyrrole-1-carboxylate
by Sung-Gon Kim
Molbank 2025, 2025(2), M1983; https://doi.org/10.3390/M1983 - 24 Mar 2025
Viewed by 179
Abstract
A highly novel method for the preparation of benzyl 2-phenyl-1H-pyrrole-1-carboxylate has been developed. The intramolecular reaction of benzyl (E)-(4-oxo-4-phenylbut-2-en-1-yl)carbamate with oxalyl chloride provided title compound in good yields. The structure of the newly synthesized compound was determined using 1 [...] Read more.
A highly novel method for the preparation of benzyl 2-phenyl-1H-pyrrole-1-carboxylate has been developed. The intramolecular reaction of benzyl (E)-(4-oxo-4-phenylbut-2-en-1-yl)carbamate with oxalyl chloride provided title compound in good yields. The structure of the newly synthesized compound was determined using 1H-, 13C-NMR, IR, and mass spectral data. Full article
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Scheme 1

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