Molbank

5 pages, 357 KB

Open AccessShort Note

N-(3-Methoxyphenethyl)-2-propylpentanamide

by Diyana Dimitrova, Yoana Barakova, Ivaylo Trifonov, Iliyan Ivanov, Dimitar Bojilov and Stanimir Manolov

Molbank 2025, 2025(4), M2114; https://doi.org/10.3390/M2114 - 17 Dec 2025

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Abstract

Herein, we present the synthesis of N-(3-methoxyphenethyl)-2-propylpentanamide, a derivative of valproic acid. The compound has been thoroughly characterized through melting-point determination, ¹H and ¹³C NMR spectroscopy, infrared spectroscopy, and mass spectrometry. The comprehensive analytical data obtained from these techniques confirm [...] Read more.

Herein, we present the synthesis of N-(3-methoxyphenethyl)-2-propylpentanamide, a derivative of valproic acid. The compound has been thoroughly characterized through melting-point determination, ¹H and ¹³C NMR spectroscopy, infrared spectroscopy, and mass spectrometry. The comprehensive analytical data obtained from these techniques confirm the successful preparation and structural integrity of the newly synthesized molecule. Full article

(This article belongs to the Section Structure Determination)

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7 pages, 1130 KB

Open AccessShort Note

Benzyl 2,4-dichlorophenyl sulfoxide

by Maria Annunziata M. Capozzi, Joan F. Piniella Febrer and Cosimo Cardellicchio

Molbank 2025, 2025(4), M2113; https://doi.org/10.3390/M2113 - 16 Dec 2025

Viewed by 84

Abstract

Benzyl 2,4-dichlorophenyl sulfoxide was synthesized both in racemic and in an enantiopure form. This enantiopure sulfoxide is a further successful confirmation of our straightforward protocol to yield easily chiral aryl benzyl sulfoxides. We solved also the crystal structure of racemic benzyl 2,4-dichlorophenyl sulfoxide [...] Read more.

Benzyl 2,4-dichlorophenyl sulfoxide was synthesized both in racemic and in an enantiopure form. This enantiopure sulfoxide is a further successful confirmation of our straightforward protocol to yield easily chiral aryl benzyl sulfoxides. We solved also the crystal structure of racemic benzyl 2,4-dichlorophenyl sulfoxide with a single crystal X-ray diffraction experiment. The main interactions building up the crystal structure were recognized and compared with other similar sulfoxides. Full article

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Graphical abstract

6 pages, 390 KB

Open AccessCommunication

Linear Synthesis of 10-Hydroxy-N,N-dimethyl-N-((3-(tosyloxy)pyridin-2-yl)methyl)decan-1-aminium Bromide

by Václav Hron, Martin Urban and Tomáš Tobrman

Molbank 2025, 2025(4), M2112; https://doi.org/10.3390/M2112 - 16 Dec 2025

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Abstract

In 2019, carbamates derived from 3-hydroxypyridine were classified as nerve agents and subsequently included in the Annex on Chemicals by the Conference of the States Parties. Herein, we describe the preparation of a structural simulant of this class of compounds, 10-hydroxy-N, [...] Read more.

In 2019, carbamates derived from 3-hydroxypyridine were classified as nerve agents and subsequently included in the Annex on Chemicals by the Conference of the States Parties. Herein, we describe the preparation of a structural simulant of this class of compounds, 10-hydroxy-N,N-dimethyl-N-((3-(tosyloxy)pyridin-2-yl)methyl)decan-1-aminium bromide. The compound was synthesized via tosylation of 2-((N,N-dimethylamino)methyl)pyridin-3-ol with tosyl chloride in the presence of sodium hydride, followed by alkylation of the resulting ((N,N-dimethylamino)methyl)pyridin-3-yl 4-methylbenzenesulfonate with 10-bromodecan-1-ol. Full article

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

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5 pages, 1074 KB

Open AccessShort Note

(1S,4R)-4,7,7-Trimethyl-1-(1H-perimidin-2-yl)-2-oxabicyclo[2.2.1]heptan-3-one

by Elżbieta Speina, Krzysztof Łyczko and Adam Mieczkowski

Molbank 2025, 2025(4), M2111; https://doi.org/10.3390/M2111 - 16 Dec 2025

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Abstract

Perimidine derivatives are versatile heterocycles with growing significance in medicinal chemistry and materials sciences. However, their structural variety remains limited. This study focused on the synthesis and crystal structure characterization of a new perimidine-based molecule. A bicyclic perimidine lactone, (1S,4R [...] Read more.

Perimidine derivatives are versatile heterocycles with growing significance in medicinal chemistry and materials sciences. However, their structural variety remains limited. This study focused on the synthesis and crystal structure characterization of a new perimidine-based molecule. A bicyclic perimidine lactone, (1S,4R)-4,7,7-trimethyl-1-(1H-perimidin-2-yl)-2-oxabicyclo[2.2.1]heptan-3-one (1), was synthesized through an intramolecular dehydration of a monoamide intermediate formed from 1,8-diaminonaphthalene and (1S)-(–)-camphanic chloride under basic conditions. The product was purified and crystallized from acetone, giving single crystals suitable for X-ray diffraction. Structural analysis revealed two stereogenic centers and crystallization in the chiral tetragonal P4₃2₁2 space group, with stabilization through N—H···O and C—H···N hydrogen bonds as well as C—H···π interactions. Full article

(This article belongs to the Collection Heterocycle Reactions)

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6 pages, 530 KB

Open AccessShort Note

(4R,4aS,6bR,8aR,12bS,14aS)-2-((E)-2-Bromo-4-chlorobenzylidene)-4,4a,6b,8a,11,11,12b,14a-octamethylicosahydropicen-3(2H)-one

by Kaichen Guan, Jinzheng Yu, Yangzhonghui Chen, Jianqin Chen, Qian Zhao, Xiaojiang Hao, Juan Xu and Xiao Ding

Molbank 2025, 2025(4), M2110; https://doi.org/10.3390/M2110 - 15 Dec 2025

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Abstract

Friedelin, a pentacyclic triterpene, has been reported to inhibit potential reactive oxygen species (ROS)-scavenging activity. Accordingly, we modified the structure of this compound with the aim of obtaining derivatives. A new derivative (compound 4), with an α,β-unsaturated ketone moiety, was synthesized via [...] Read more.

Friedelin, a pentacyclic triterpene, has been reported to inhibit potential reactive oxygen species (ROS)-scavenging activity. Accordingly, we modified the structure of this compound with the aim of obtaining derivatives. A new derivative (compound 4), with an α,β-unsaturated ketone moiety, was synthesized via an aldol condensation. Structural characterization of this compound was performed using nuclear magnetic resonance (NMR) spectroscopy and high-resolution electrospray ionization mass spectrometry. Full article

(This article belongs to the Section Natural Product Chemistry)

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8 pages, 529 KB

Open AccessCommunication

Synthesis of 3,5-Diamino-Substituted Dithieno[3,2-b:2′,3′-d]thiophene Derivatives

by Roman A. Irgashev and Nikita A. Kazin

Molbank 2025, 2025(4), M2109; https://doi.org/10.3390/M2109 - 10 Dec 2025

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Abstract

We report the first synthesis of 3,5-diamino-substituted dithieno[3,2-b:2′,3′-d]thiophene derivatives, bearing alkoxycarbonyl or acetyl groups at C-2 and C-6 positions. The target compounds were prepared via the reaction of 3,4-dibromothiophene-2,5-dicarbonitrile with alkyl thioglycolates or mercaptoacetone in the presence of DBU [...] Read more.

We report the first synthesis of 3,5-diamino-substituted dithieno[3,2-b:2′,3′-d]thiophene derivatives, bearing alkoxycarbonyl or acetyl groups at C-2 and C-6 positions. The target compounds were prepared via the reaction of 3,4-dibromothiophene-2,5-dicarbonitrile with alkyl thioglycolates or mercaptoacetone in the presence of DBU and isolated in 67–87% yield. The key dinitrile was synthesized in 76% yield from 3,4-dibromothiophene-2,5-dicarbaldehyde. In turn, this dialdehyde was prepared on a multigram scale from commercially available 2,5-dimethylthiophene in three steps. The resulting dithieno[3,2-b:2′,3′-d]thiophenes serve as valuable building blocks for materials chemistry, offering multiple reactive sites for further structural elaboration and property tuning. Full article

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

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4 pages, 673 KB

Open AccessShort Note

(S)-2-((E)-2-((S)-2-Methyl-5-(prop-1-en-2-yl)cyclopent-1-en-1-yl)vinyl)-5-(prop-1-en-2-yl)cyclopent-1-ene-1-carbaldehyde

by Andrea Marrero-González, Juan F. Rodríguez-Caro, María M. Afonso and José Antonio Palenzuela

Molbank 2025, 2025(4), M2108; https://doi.org/10.3390/M2108 - 10 Dec 2025

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Abstract

(S)-2-methyl-5-(prop-1-en-2-yl)cyclopent-1-ene-1-carbaldehyde (2) is a component of the essential oils of several plants and has also been used in many syntheses, usually of terpenes. Although the preparation of compound 2 has been reported several times, no side products have been [...] Read more.

(S)-2-methyl-5-(prop-1-en-2-yl)cyclopent-1-ene-1-carbaldehyde (2) is a component of the essential oils of several plants and has also been used in many syntheses, usually of terpenes. Although the preparation of compound 2 has been reported several times, no side products have been reported previously. In this Short Note, we present the identification of one such side product. This new compound (3) arises from a vinylogous aldol autocondensation, occurring after the formation of 2, even when the reaction runs for a short time. However, it can diminish the yield of 2 when the reaction is allowed to continue for a longer time. Full article

(This article belongs to the Collection Molecules from Side Reactions)

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Graphical abstract

5 pages, 986 KB

Open AccessShort Note

1β, 6α-Dihydroxy-5αH-eudesma-3(4), 11(13)-dien-12, 8β-olide

by Dan-Dan Xu, Jie-Yi Ren, Zhen-Ning Wu, Yi-Yu Qi and Jiang-Jiang Tang

Molbank 2025, 2025(4), M2107; https://doi.org/10.3390/M2107 - 10 Dec 2025

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Abstract

1β, 6α-dihydroxy-5αH-eudesma-3(4), 11(13)-dien-12, 8β-olide is a natural eudesmane sesquiterpene lactone isolated from the aerial parts of Inula nervosa Wall. In this paper, we report the X-ray crystallography of the compound 1 for the first time, along with the 1D/2D NMR spectra. Full article

(This article belongs to the Section Natural Product Chemistry)

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8 pages, 502 KB

Open AccessShort Note

7,7′-(1,4-Phenylene)bis(2-benzyl-3-(3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one)

by Roberto E. Blanco-Carapia, Alejandro Islas-Jácome and Eduardo González-Zamora

Molbank 2025, 2025(4), M2106; https://doi.org/10.3390/M2106 - 10 Dec 2025

Viewed by 133

Abstract

The multicomponent synthesis of a novel and highly symmetric polyheterocycle based on the pyrrolo[3,4-b]pyridin-5-one core incorporating the privileged tetrahydroisoquinoline moiety is described. The target compound was synthesized as an inseparable mixture of stereoisomers through a pseudo-repetitive Ugi–Zhu five-component reaction (PR-UZ-5CR) coupled [...] Read more.

The multicomponent synthesis of a novel and highly symmetric polyheterocycle based on the pyrrolo[3,4-b]pyridin-5-one core incorporating the privileged tetrahydroisoquinoline moiety is described. The target compound was synthesized as an inseparable mixture of stereoisomers through a pseudo-repetitive Ugi–Zhu five-component reaction (PR-UZ-5CR) coupled to a double post-transformation sequence involving an intermolecular aza Diels–Alder cycloaddition, an intramolecular N-acylation, and a final tandem aromatization step. The product was prepared in 63% overall yield, and with an excellent atom economy of 85%, within a total reaction time of 85 min, and a temperature range from 25 to 65 °C. Structural elucidation and molecular mass confirmation were successfully achieved through NMR and FT-IR spectroscopy, and high-resolution mass spectrometry (HRMS), respectively. Full article

(This article belongs to the Collection Heterocycle Reactions)

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5 pages, 628 KB

Open AccessShort Note

9-Oxo-2-(p-tolyl)-4,9-dihydropyrazolo[5,1-b]quinazoline-3a(3H)-carboxylic Acid

by Anastasia A. Andreeva, Yurii V. Shklyaev and Andrey N. Maslivets

Molbank 2025, 2025(4), M2105; https://doi.org/10.3390/M2105 - 8 Dec 2025

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Abstract

Compounds based on the pyrazoloquinazoline scaffold are of significant interest in synthetic organic chemistry owing to their potential biological activity. In this work, we describe the synthesis of a new derivative with this scaffold, 9-oxo-2-(p-tolyl)-4,9-dihydropyrazolo[5,1-b]quinazoline-3a(3H)-carboxylic acid, obtained [...] Read more.

Compounds based on the pyrazoloquinazoline scaffold are of significant interest in synthetic organic chemistry owing to their potential biological activity. In this work, we describe the synthesis of a new derivative with this scaffold, 9-oxo-2-(p-tolyl)-4,9-dihydropyrazolo[5,1-b]quinazoline-3a(3H)-carboxylic acid, obtained by reacting 2,4-dioxo-4-(p-tolyl)butanoic acid with 2-aminobenzohydrazide in a 1:1 ratio when mixed in ethanol. The compound was characterized by ¹H/¹³C NMR, IR, and X-ray diffraction analysis. Full article

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7 pages, 1110 KB

Open AccessShort Note

P,P,P′,P′-Tetraisopropyl(1,4-phenylenebis(hydroxymethylene))bis(phosphonate)

by Jaden K. Jones, Aidan P. McKay, David B. Cordes and Brian A. Chalmers

Molbank 2025, 2025(4), M2104; https://doi.org/10.3390/M2104 - 8 Dec 2025

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Abstract

We report the synthesis and molecular structure as determined by single-crystal X-ray diffraction of P,P,P′,P′-tetraisopropyl(1,4-phenylenebis(hydroxymethylene))bis(phosphonate). The compound was fully characterized 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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Graphical abstract

4 pages, 361 KB

Open AccessShort Note

N-(9-Ethyl-9H-carbazol-2-yl)-N′-(1-phenylethyl)thiourea

by Agnieszka Maksymiuk-Kłos, Rafał Słapa, Marek Bartkowiak, Radosław Michalik, Monika Pazura-Turowska, Dorota Szubińska-Lelonkiewicz and Anna Bielenica

Molbank 2025, 2025(4), M2103; https://doi.org/10.3390/M2103 - 5 Dec 2025

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Abstract

Substituted thiourea derivatives represent a structurally diverse group of compounds with high biological activity. In this paper, we present the synthesis of N-(9-ethyl-9H-carbazol-2-yl)-N′-(1-phenylethyl)thiourea by condensation reaction. The structure of the title compound was confirmed by ¹H and [...] Read more.

Substituted thiourea derivatives represent a structurally diverse group of compounds with high biological activity. In this paper, we present the synthesis of N-(9-ethyl-9H-carbazol-2-yl)-N′-(1-phenylethyl)thiourea by condensation reaction. The structure of the title compound was confirmed by ¹H and ¹³C nuclear magnetic resonance (NMR), Fourier-transform infrared spectroscopy (FT-IR), and high-resolution mass spectrometry (HRMS). Full article

(This article belongs to the Collection Heterocycle Reactions)

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7 pages, 729 KB

Open AccessShort Note

Bis(1,2,4-triphenylcyclopentadienyl) Terbium 4,4,4-trifluoro-1-phenylbutane-1,3-dionate

by Daniil A. Bardonov, Mikhail E. Minyaev, Lada N. Puntus, Ilya E. Nifant’ev and Dmitrii M. Roitershtein

Molbank 2025, 2025(4), M2102; https://doi.org/10.3390/M2102 - 4 Dec 2025

Viewed by 187

Abstract

A new bis(cyclopentadienyl) terbium(III) complex with 1,2,4-triphenylcyclopentadienyl and 4,4,4-trifluoro-1-phenylbutane-1,3-dionate ligands was synthesized. Single-crystal X-ray analysis revealed a mononuclear bis(cyclopentadienyl) complex with a diketonate ligand in the bisector plane. The compound under study exhibits a ligand ligand charge transfer state (LLCT), according to optical [...] Read more.

A new bis(cyclopentadienyl) terbium(III) complex with 1,2,4-triphenylcyclopentadienyl and 4,4,4-trifluoro-1-phenylbutane-1,3-dionate ligands was synthesized. Single-crystal X-ray analysis revealed a mononuclear bis(cyclopentadienyl) complex with a diketonate ligand in the bisector plane. The compound under study exhibits a ligand ligand charge transfer state (LLCT), according to optical spectroscopy and crystallographic data. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

5 pages, 465 KB

Open AccessShort Note

Methyl (1aRS,7aSR)-7-formyl-1a-phenyl-1,1a-dihydroazirino[2,3-b]benzo[e][1,4]thiazine-7a(7H)-carboxylate

by Ilya P. Filippov, Anastasiya V. Agafonova, Nikolai V. Rostovskii and Mikhail S. Novikov

Molbank 2025, 2025(4), M2101; https://doi.org/10.3390/M2101 - 4 Dec 2025

Viewed by 159

Abstract

The first representative of the aziridine-fused benzo[e][1,4]thiazine series was synthesized from methyl 2-bromo-2-phenyl-2H-azirine-2-carboxylate and benzo[d]thiazole in 74% yield. The reaction proceeds via the S_N2′-S_N2′-cascade to form the azirinylthiazolium salt followed by a [...] Read more.

The first representative of the aziridine-fused benzo[e][1,4]thiazine series was synthesized from methyl 2-bromo-2-phenyl-2H-azirine-2-carboxylate and benzo[d]thiazole in 74% yield. The reaction proceeds via the S_N2′-S_N2′-cascade to form the azirinylthiazolium salt followed by a water-induced thiazole ring expansion. The structure of the title compound was established based on ¹H, ¹³C, 2D NMR spectroscopy and high-resolution mass spectrometry, and unambiguously confirmed by X-ray diffraction analysis. Full article

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

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Graphical abstract

5 pages, 453 KB

Open AccessShort Note

(E)-8-(4-(4-(Diphenylamino)styryl)phenoxy)-N,N,N-trimethyloctan-1-aminium Bromide

by Saiya Yang, Ya-Na Wang, Yuyang Ma, Ruirui Li, Maxwell Ampomah-Wireko, Cedric Dzidzor Kodjo Amengor, En Zhang and Yi-Hong Zhao

Molbank 2025, 2025(4), M2100; https://doi.org/10.3390/M2100 - 3 Dec 2025

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Abstract

Structural optimization integrating triphenylamine and quaternary ammonium salt-based antimicrobial peptide mimics has yielded novel theranostic hybrid molecules. These compounds exhibit fluorescence imaging, photodynamic antibacterial activity, and membrane-disruption capabilities, demonstrating broad-spectrum efficacy with low resistance induction. In this study, we successfully developed a novel [...] Read more.

Structural optimization integrating triphenylamine and quaternary ammonium salt-based antimicrobial peptide mimics has yielded novel theranostic hybrid molecules. These compounds exhibit fluorescence imaging, photodynamic antibacterial activity, and membrane-disruption capabilities, demonstrating broad-spectrum efficacy with low resistance induction. In this study, we successfully developed a novel triphenylamine-quaternary ammonium derivative (TPQ), ultimately obtaining the target compound (E)-8-(4-(4-(diphenylamino)styryl)phenoxy)-N,N,N-trimethyloctan-1-aminium bromide (Compound 5). This achievement provides a potent strategy against growing bacterial drug resistance. Full article

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4 pages, 762 KB

Open AccessShort Note

(Z)-N-Carbamothioyl-4-hydroxy-2-oxo-4-(p-tolyl)but-3-enamide

by Alexandra O. Derevnina, Yurii V. Shklyaev and Andrey N. Maslivets

Molbank 2025, 2025(4), M2099; https://doi.org/10.3390/M2099 - 2 Dec 2025

Viewed by 177

Abstract

The reaction of 5-(p-tolyl)furan-2,3-dione with thiourea in a 1:1 ratio when refluxed in 1,4-dioxane gives (Z)-N-carbamothioyl-4-hydroxy-2-oxo-4-(p-tolyl)but-3-enamide with a good yield. This compound was fully characterized. Full article

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5 pages, 419 KB

Open AccessCommunication

Synthesis and Characterization of Three New Furan-Containing Terpyridine Derivatives

by Jérôme Husson

Molbank 2025, 2025(4), M2098; https://doi.org/10.3390/M2098 - 2 Dec 2025

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Abstract

Three new terpyridine derivatives which contain a pendant furan heterocycle have been prepared and characterized. The first two, 4′-(4,5-dimethylfuran-2-yl)-2,2′:6′,2″-terpyridine (1) and 4′-((1,3-dioxolan-2-yl)furan-2-yl)-2,2′:6′,2″-terpyridine (2), are obtained through the reaction of 2-acetylpyridine and suitable furaldehydes using the Kröhnke reaction. The last [...] Read more.

Three new terpyridine derivatives which contain a pendant furan heterocycle have been prepared and characterized. The first two, 4′-(4,5-dimethylfuran-2-yl)-2,2′:6′,2″-terpyridine (1) and 4′-((1,3-dioxolan-2-yl)furan-2-yl)-2,2′:6′,2″-terpyridine (2), are obtained through the reaction of 2-acetylpyridine and suitable furaldehydes using the Kröhnke reaction. The last one, 4′-(5-formylfuran-2-yl)-2,2′:6′,2′’-terpyridine (3) is obtained via acidic hydrolysis of the acetal onto terpyridine (2). The structures of these new compounds are confirmed using different analytical techniques such as NMR and infrared spectroscopy (ATR-IR) as well as by High Resolution Mass Spectrometry (HRMS). Full article

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

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7 pages, 743 KB

Open AccessShort Note

1-[4-(4-Chlorophenyl)piperazin-1-yl]-2-[(4-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]ethan-1-one

by Wiktoria Drzał, Jarosław Sobstyl and Nazar Trotsko

Molbank 2025, 2025(4), M2097; https://doi.org/10.3390/M2097 - 2 Dec 2025

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Abstract

Heterocyclic systems such as 1,2,4-triazoles and piperazines play an important role in modern medicinal chemistry due to their structural diversity and broad spectrum of biological activities. In this Short Note, we report the synthesis and spectroscopic characterization of a new hybrid molecule combining [...] Read more.

Heterocyclic systems such as 1,2,4-triazoles and piperazines play an important role in modern medicinal chemistry due to their structural diversity and broad spectrum of biological activities. In this Short Note, we report the synthesis and spectroscopic characterization of a new hybrid molecule combining both pharmacophoric fragments: 1-[4-(4-chlorophenyl)piperazin-1-yl]-2-[(4-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]ethan-1-one (compound 3). The compound was obtained in 70% yield via S-alkylation of 4-phenyl-1,2,4-triazole-3-thione with a chloroacetyl derivative of 4-chlorophenylpiperazine under alkaline conditions. The structure of 3 was confirmed by ¹H and ¹³C NMR spectroscopy, DEPT-135, 2D NMR (COSY, NOESY, HSQC, HMBC), FT-IR, and elemental analysis. These results support the utility of combining triazole and piperazine fragments in the design of new heterocyclic frameworks with potential biological relevance. Full article

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7 pages, 682 KB

Open AccessShort Note

(7aR*,7bR*)-7a,7b-Dihydro-15H-dibenzo[f,f′]cyclopenta[1,2-b:5,4-b′]dichromene

by Dmitry V. Osipov, Oleg P. Demidov and Vitaly A. Osyanin

Molbank 2025, 2025(4), M2096; https://doi.org/10.3390/M2096 - 27 Nov 2025

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Abstract

The reaction of a 2-naphthol-derived Mannich base with the push-pull 5-morpholinopenta-2,4-dienal under acidic conditions unexpectedly afforded (7aR*,7bR*)-7a,7b-dihydro-15H-dibenzo[f,f′]cyclopenta[1,2-b:5,4-b′]dichromene. The structure of this product was unambiguously confirmed by NMR spectroscopy and [...] Read more.

The reaction of a 2-naphthol-derived Mannich base with the push-pull 5-morpholinopenta-2,4-dienal under acidic conditions unexpectedly afforded (7aR*,7bR*)-7a,7b-dihydro-15H-dibenzo[f,f′]cyclopenta[1,2-b:5,4-b′]dichromene. The structure of this product was unambiguously confirmed by NMR spectroscopy and X-ray diffraction analysis. A plausible mechanism involves the in situ generation of 1,2-naphthoquinone-1-methide, followed by a [4 + 2] cycloaddition and a subsequent interrupted iso-Nazarov cyclization. In this process, the enol tautomer of the resulting fused cyclopentenone is trapped by a second equivalent of the 1,2-naphthoquinone-1-methide, leading to the observed polycyclic framework. Full article

(This article belongs to the Collection Heterocycle Reactions)

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4 pages, 378 KB

Open AccessCommunication

Three-Step Synthesis of (E)-1-(2-(Pyridin-2-yl)benzo[d]thiazol-6-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one as a Potential Ligand for Transition Metals

by Yordanka B. Ivanova and Ognyan I. Petrov

Molbank 2025, 2025(4), M2095; https://doi.org/10.3390/M2095 - 21 Nov 2025

Viewed by 251

Abstract

In the present study, (E)-1-(2-(pyridin-2-yl)benzo[d]thiazol-6-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (4) was designed and synthesized via a three-step reaction sequence. Initially, 6-acetylbenzo[d]thiazol-2(3H)-one (1) was hydrolyzed to the corresponding 5-acetyl-2-aminothiophenol 2 and then cyclized with pyridine-2-carbaldehyde. The [...] Read more.

In the present study, (E)-1-(2-(pyridin-2-yl)benzo[d]thiazol-6-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (4) was designed and synthesized via a three-step reaction sequence. Initially, 6-acetylbenzo[d]thiazol-2(3H)-one (1) was hydrolyzed to the corresponding 5-acetyl-2-aminothiophenol 2 and then cyclized with pyridine-2-carbaldehyde. The final product was synthesized by a base-catalyzed aldol condensation of 1-(2-(pyridin-2-yl)benzo[d]thiazol-6-yl)ethan-1-one (3) and 3,4,5-trimethoxybenzaldehyde and was comprehensively characterized. Full article

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Graphical abstract

11 pages, 965 KB

Open AccessShort Note

Mixed-Ligand Copper(II) Complex with Ethyl (2-(Methylcarbamoyl)phenyl)carbamate and 3-Methylquinazoline-2,4(1H,3H)-dione

by Petya Emilova Marinova, Nikola Burdzhiev, Evelina Varbanova, Slava Tsoneva and Stoyanka Nikolova

Molbank 2025, 2025(4), M2094; https://doi.org/10.3390/M2094 - 21 Nov 2025

Viewed by 259

Abstract

(This paper presents the synthesis of a novel copper(II) metal complex with ethyl (2-(methylcarbamoyl)phenyl)carbamate and 3-methylquinazoline-2,4(1H,3H)-dione. The characterization of the compound was conducted through various techniques, including melting point determination, microwave plasma atomic emission spectrometry (MP-AES) for Cu, attenuated [...] Read more.

(This paper presents the synthesis of a novel copper(II) metal complex with ethyl (2-(methylcarbamoyl)phenyl)carbamate and 3-methylquinazoline-2,4(1H,3H)-dione. The characterization of the compound was conducted through various techniques, including melting point determination, microwave plasma atomic emission spectrometry (MP-AES) for Cu, attenuated total reflection (ATR), IR, ¹H NMR, and ¹³C NMR spectroscopy. The coordination compound was obtained after mixing water solutions of the metal salt and the ligand dissolved in DMSO and water solutions of NaOH, in a metal-to-ligand-to-base ratio of 1:2:2. The ligand and the metal chloride were brought into the reaction at room temperature in DMSO and H₂O as solvents, respectively. The results indicate the successful formation of a stable mixed-ligand Cu(II) coordination compound involving N,O-donor ligands. Based on the obtained data, we assumed that the ligands are coordinated through N- and O-donor atoms. Spectroscopic data suggested that the ligand (3-methylquinazoline-2,4(1H,3H)-dione), by using (NaOH), coordinated to a metal ion as a monodentate ligand through the nitrogen atom of the NH group and ethyl (2-(methylcarbamoyl)phenyl)carbamate coordinated in a bidentate fashion through the N- and O-donor atoms of ester group. Additionally, two hydroxyl groups were bridged for two metal ions into the formed dimer structure. Full article

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6 pages, 1768 KB

Open AccessShort Note

2-(Difluoroboryloxy)benzamide

by R. Alan Aitken, Hibet E. M. Akkache, David B. Cordes, Aidan P. McKay and Dorian Moreau

Molbank 2025, 2025(4), M2093; https://doi.org/10.3390/M2093 - 20 Nov 2025

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Abstract

The title compound has been fully characterised by NMR for the first time. Fully assigned ¹H and ¹³C NMR spectra, and the X-ray structure of two different polymorphs are presented. The polymorphs show similar molecular geometries but exhibit significantly different patterns [...] Read more.

The title compound has been fully characterised by NMR for the first time. Fully assigned ¹H and ¹³C NMR spectra, and the X-ray structure of two different polymorphs are presented. The polymorphs show similar molecular geometries but exhibit significantly different patterns of intermolecular interactions. Full article

(This article belongs to the Section Structure Determination)

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6 pages, 614 KB

Open AccessCommunication

Schiff Base Heterobimetallic Complex as Single-Source Precursor

by Jocelyn Pradegan, Aurélien Crochet and Katharina M. Fromm

Molbank 2025, 2025(4), M2092; https://doi.org/10.3390/M2092 - 20 Nov 2025

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Abstract

A bimetallic complex based on a salophen-type ligand was synthesized. The compound was characterized by ESI-MS, single-crystal, and powder X-ray diffraction. The heterobimetallic complex was thermally treated to investigate its capacity as a single-source precursor for the formation of mixed metal oxides. Full article

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6 pages, 256 KB

Open AccessShort Note

2,5-Dimethylbenzyl 2-{(4,6-diaminopyrimidin-2-yl)thio}acetate

by Gulrukh Salieva, Malokhat Uktamova, Sardorbek Otajonov, Kohei Torikai and Tursunali Kholikov

Molbank 2025, 2025(4), M2091; https://doi.org/10.3390/M2091 - 19 Nov 2025

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Abstract

2,5-Dimethylbenzyl 2-{(4,6-diaminopyrimidin-2-yl)thio}acetate was prepared by an alkylation reaction between the sodium salt of 4,6-diamino-2-mercaptopyrimidine and chloroacetic acid. The structure was unambiguously elucidated based on high-resolution mass spectrometry (HRMS) as well as spectroscopies such as infrared (IR) and nuclear magnetic resonance (NMR). Full article

(This article belongs to the Collection Heterocycle Reactions)

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8 pages, 1182 KB

Open AccessShort Note

Trichloro[2,5-bis[N-(4-isopropylphenyl)-P,P-diisopropylphosphorimidoyl-κN]pyrrole-κN]zirconium(IV)·Benzene

by Thamara V. Salazar-Barrientos, Christopher P. Forfar and Paul G. Hayes

Molbank 2025, 2025(4), M2090; https://doi.org/10.3390/M2090 - 14 Nov 2025

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Abstract

A new zirconium trichloride complex, supported by a monoanionic, pyrrole-based bisphosphinimine NNN-pincer ligand, [LZrCl₃] (L = 2,5-[ⁱPr₂P=N(4-ⁱPrC₆H₄)]₂NH(C₆H₂) (1), is reported. Comparison with [...] Read more.

A new zirconium trichloride complex, supported by a monoanionic, pyrrole-based bisphosphinimine NNN-pincer ligand, [LZrCl₃] (L = 2,5-[ⁱPr₂P=N(4-ⁱPrC₆H₄)]₂NH(C₆H₂) (1), is reported. Comparison with a related iminopincer complex reveals significant differences in bond lengths and angles between the atoms around the metal centre, largely due to the more electron donating phosphinimine (R₃P=NR (R = alkyl, aryl)) functionality. The P=N bonds in complex (1•benzene) are longer than in the proteo ligand HL (L = 2,5-[Ph₂P=N(4-ⁱPrC₆H₄)]₂NH(C₆H₂)), which is consistent with phosphinimine coordination to a metal. This is the only reported zirconium complex with this specific ligand scaffold; no analogous complexes have been reported for other group 4 metals. This structure expands the library of Zr pincer complexes that bear tridentate ligand frameworks and sets the stage for the preparation of related complexes. Full article

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6 pages, 996 KB

Open AccessShort Note

N,N′-Di(p-tolyl)-1,4-benzoquinonediimine (N,N′-Di-p-tolylcyclohexa-2,5-diene-1,4-diimine)

by R. Alan Aitken, Rebecca Bascombe and Alexandra M. Z. Slawin

Molbank 2025, 2025(4), M2089; https://doi.org/10.3390/M2089 - 13 Nov 2025

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Abstract

The title compound has been fully characterised using ¹H and ¹³C NMR spectroscopy, which reveals (E) to (Z) isomerisation upon dissolution. In the solid state, X-ray diffraction shows exclusively the (E)-isomer with two geometrically near-identical [...] Read more.

The title compound has been fully characterised using ¹H and ¹³C NMR spectroscopy, which reveals (E) to (Z) isomerisation upon dissolution. In the solid state, X-ray diffraction shows exclusively the (E)-isomer with two geometrically near-identical independent molecules each with the outer rings tilted with respect to the central ring. Full article

(This article belongs to the Section Structure Determination)

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5 pages, 615 KB

Open AccessShort Note

(1R,2R,6S)-3-Methyl-6-(3-(4-phenylpiperidin-1-yl)prop-1-en-2-yl)cyclohex-3-ene-1,2-diol

by Alexandra V. Podturkina, Nikolai S. Li-Zhulanov, Tatyana V. Rybalova, Konstantin P. Volcho and Nariman F. Salakhutdinov

Molbank 2025, 2025(4), M2088; https://doi.org/10.3390/M2088 - 12 Nov 2025

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Abstract

Parkinson’s disease (PD) is a progressive neurodegenerative disorder whose primary manifestation is motor dysfunction. Previous research showed that (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol (Prottremine) exhibits potent antiparkinsonian activity in animal models of PD, with an efficacy comparable to levodopa. Herein, we [...] Read more.

Parkinson’s disease (PD) is a progressive neurodegenerative disorder whose primary manifestation is motor dysfunction. Previous research showed that (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol (Prottremine) exhibits potent antiparkinsonian activity in animal models of PD, with an efficacy comparable to levodopa. Herein, we report the synthesis of a new Prottremine derivative, (1R,2R,6S)-3-methyl-6-(3-(4-phenylpiperidin-1-yl)prop-1-en-2-yl)cyclohex-3-ene-1,2-diol. The compound was fully characterized and its structure was confirmed through single-crystal X-ray diffraction analysis. Full article

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6 pages, 329 KB

Open AccessShort Note

(E)-4-(4-((8-Bromooctyl)oxy)styryl)-N,N-diphenylaniline

by Yi-Qiong Sun, Ya-Na Wang, Kai-Wei Zhu, Ruirui Li, Maxwell Ampomah-Wireko, Cedric Dzidzor Kodjo Amengor, En Zhang and Yi-Hong Zhao

Molbank 2025, 2025(4), M2087; https://doi.org/10.3390/M2087 - 10 Nov 2025

Cited by 1 | Viewed by 288

Abstract

Triphenylamine and phenol derivatives are two types of antimicrobial molecules with broad application prospects. Through functional modification, these compounds integrate fluorescence imaging and photodynamic antibacterial therapy, thereby achieving theranostic capabilities. They exert broad-spectrum and highly efficient antimicrobial activity via a membrane-disrupting mechanism, which [...] Read more.

Triphenylamine and phenol derivatives are two types of antimicrobial molecules with broad application prospects. Through functional modification, these compounds integrate fluorescence imaging and photodynamic antibacterial therapy, thereby achieving theranostic capabilities. They exert broad-spectrum and highly efficient antimicrobial activity via a membrane-disrupting mechanism, which consequently reduces the propensity for inducing drug resistance. In this work, triphenylamine-phenol derivatives (TPO) were designed and synthesized through three consecutive reactions: Wittig reaction, Heck reaction, and substitution reaction. Double bonds, hydroxyl groups, and brominated alkyl chains were gradually introduced to finally obtain the target product (E)-4-(4-((8-bromooctyl)oxy)styryl)-N,N-diphenylaniline (5). This study provides new insights into the development of novel and highly efficient antibacterial agents. Full article

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7 pages, 1111 KB

Open AccessShort Note

Bromo(5-cyclohexyl-1-methyl-1H-1,2,4-triazol-4-ium-3-yl)bis(triphenylphosphane)palladium Tetrafluoroborate

by Andrey Y. Chernenko, Igor V. Lavrentev, Maxim A. Shevchenko, Mikhail E. Minyaev, Konstantin E. Shepelenko and Victor M. Chernyshev

Molbank 2025, 2025(4), M2086; https://doi.org/10.3390/M2086 - 10 Nov 2025

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Abstract

Transition metal complexes bearing protic N-heterocyclic carbene (pNHC) ligands are promising precatalysts for organic reactions due to their capacity for unique hydrogen-bonding interactions. Herein, we report the synthesis and structural characterization of the first Pd(II) complex featuring a pNHC derived from 1,2,4-triazole—a heterocyclic [...] Read more.

Transition metal complexes bearing protic N-heterocyclic carbene (pNHC) ligands are promising precatalysts for organic reactions due to their capacity for unique hydrogen-bonding interactions. Herein, we report the synthesis and structural characterization of the first Pd(II) complex featuring a pNHC derived from 1,2,4-triazole—a heterocyclic system previously unexplored for the preparation of metal/pNHC complexes. The complex was synthesized via oxidative addition of 3-bromo-5-cyclohexyl-1-methyl-1H-1,2,4-triazole to Pd(PPh₃)₄ in the presence of NH₄BF₄. Its molecular structure was characterized by NMR spectroscopy and X-ray diffraction analysis. Full article

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

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7 pages, 603 KB

Open AccessCommunication

Synthesis of a Stable Long-Wavelength Fluorescent BODIPY FL-NAADP Conjugate

by Zhong Guan and James T. Slama

Molbank 2025, 2025(4), M2085; https://doi.org/10.3390/M2085 - 5 Nov 2025

Viewed by 383

Abstract

Nicotinic acid adenine dinucleotide phosphate (NAADP) is a second messenger that stimulates intracellular Ca²⁺ release in both mammalian cells and echinoderm egg homogenates. A NAADP linked covalently to a stable long-wavelength fluorescent dye would be a useful probe with which to characterize [...] Read more.

Nicotinic acid adenine dinucleotide phosphate (NAADP) is a second messenger that stimulates intracellular Ca²⁺ release in both mammalian cells and echinoderm egg homogenates. A NAADP linked covalently to a stable long-wavelength fluorescent dye would be a useful probe with which to characterize NAADP–receptor interactions in solution and potentially to determine intracellular-binding localization. We report the synthesis of a BODIPY-NAADP covalent conjugate made through linking the carboxyl group of BODIPY FL to the primary amino group of 5-(3-aminopropyl)-NAADP through amide bond formation. The starting pyridine dinucleotide analog, 5-(3-aminopropyl)-NAADP was available through enzyme-catalyzed base exchange between NADP and a substituted nicotinic acid analog. The resulting 5-BODIPY-NAADP conjugate was purified to homogeneity using ion-exchange chromatography, was produced in milligram quantities, and its spectroscopic properties were characterized. Full article

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