Molbank

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

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

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

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

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

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

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

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

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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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

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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7 pages, 958 KiB

Open AccessShort 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

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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Graphical abstract

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

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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6 pages, 1285 KiB

Open AccessShort 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

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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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

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

Open AccessShort 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

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

Open AccessShort 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

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

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

Open AccessCommunication

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

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

Open AccessCommunication

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

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

Open AccessCommunication

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

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

Open AccessCommunication

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

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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