Molbank

4 pages, 744 KiB

Open AccessShort Note

Ethyl 4-((11-(Hexylamino)-11-oxoundecyl)oxy)benzoate

by Jorge Jesús Montes-Patiño, Nancy Patricia Díaz-Zavala, Samuel Zapién-Castillo, Philippe J. Mésini, Jessica Ismalé Lozano-Navarro, Lorena Margarita Salas-Ordaz and Marco Antonio Aguirre-Lam

Molbank 2024, 2024(2), M1829; https://doi.org/10.3390/M1829 - 27 May 2024

Viewed by 153

Abstract

Ethyl 4-((11-(hexylamino)-11-oxoundecyl)oxy)benzoate was synthesized using 11-bromoundecanoic acid hexylamide and commercially available ethyl 4-hydroxybenzoate through a Williamson etherification synthesis. The structural characterization was performed using UV-Vis, FT-IR, ¹H-NMR, ¹³C-NMR, and HRMS. Full article

(This article belongs to the Section Organic Synthesis)

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6 pages, 1175 KiB

Open AccessShort Note

Hept-6-en-1-yl Furan-2-carboxylate

by Zhongwei Wang, Lin Song and Yukun Qin

Molbank 2024, 2024(2), M1828; https://doi.org/10.3390/M1828 - 27 May 2024

Viewed by 167

Abstract

This study aims to develop an efficient and green one-pot method for the synthesis of 6-en-1-yl furan-2-carboxylic acid heptyl ester. Initially, using furfural as the starting substrate, hept-6-en-1-yl furan-2-carboxylate was prepared using a one-pot method. This study developed a new experimental scheme for [...] Read more.

This study aims to develop an efficient and green one-pot method for the synthesis of 6-en-1-yl furan-2-carboxylic acid heptyl ester. Initially, using furfural as the starting substrate, hept-6-en-1-yl furan-2-carboxylate was prepared using a one-pot method. This study developed a new experimental scheme for preparing ester compounds, using cuprous chloride as a catalyst and tert butyl hydrogen peroxide as an oxidant to prepare furoic acid. Without the need for intermediate treatment, the target product can be directly obtained from furfural by adding 7-bromo-1-heptene, TBAB, and potassium carbonate. This method effectively utilizes furfural as a platform chemical, demonstrating its potential for synthesizing high-value chemicals. The entire synthesis process is simple and efficient, following the principles of green chemistry. Full article

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13 pages, 1848 KiB

Open AccessCommunication

Synthesis and Antibacterial Studies of a New Au(III) Complex with 6-Methyl-2-Thioxo-2,3-Dihydropyrimidin-4(1H)-One

by Petya Marinova, Nikola Burdzhiev, Denica Blazheva and Aleksandar Slavchev

Molbank 2024, 2024(2), M1827; https://doi.org/10.3390/M1827 - 24 May 2024

Viewed by 227

Abstract

This article describes the synthesis of a new metal complex using 6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one. The compound was analyzed using several methods, including determining its melting point and employing UV-Vis, IR, ATR, ¹H NMR, HSQC, and Raman spectroscopy for the free ligand. The [...] Read more.

This article describes the synthesis of a new metal complex using 6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one. The compound was analyzed using several methods, including determining its melting point and employing UV-Vis, IR, ATR, ¹H NMR, HSQC, and Raman spectroscopy for the free ligand. The metal complex was formed by combining aqueous solutions of metal salts with the ligand dissolved in DMSO and water, along with NaOH in a metal-to-ligand-to-base ratio of 1:4:2. The NMR signals of the ligand were assigned using ¹H-¹H COSY, DEPT-135, HMBC, and HMQC spectra. Furthermore, the compound’s antimicrobial activity against Gram-positive and Gram-negative bacteria, as well as yeasts, was assessed. Full article

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6 pages, 701 KiB

Open AccessCommunication

Structural Modification of Epigallocatechin-3-gallate to (2R,3R)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-3-yl l-valinate in Four Steps

by Xiaoman Yu, Zimo Ren, Paolo Coghi and Jerome P. L. Ng

Molbank 2024, 2024(2), M1826; https://doi.org/10.3390/M1826 - 23 May 2024

Viewed by 210

Abstract

Tea is a daily drink for most people, and one of its major ingredients, epigallocatechin-3-gallate (EGCG), has been widely recognized as a potent antioxidant with diverse biological activities. However, its low stability and bioavailability hinder its further clinical applications. In this study, we [...] Read more.

Tea is a daily drink for most people, and one of its major ingredients, epigallocatechin-3-gallate (EGCG), has been widely recognized as a potent antioxidant with diverse biological activities. However, its low stability and bioavailability hinder its further clinical applications. In this study, we designed and synthesized a novel EGCG-valine derivative 4 by replacing the gallic acid with a valine moiety in four steps. The structural elucidation of derivative 4 was performed using NMR, IR, mass, and UV spectroscopies. Additionally, the physicochemical properties of 4 were predicted by SwissADME, showing improved drug-like parameters and intestinal absorption compared to the parent compound EGCG. Full article

(This article belongs to the Section Organic Synthesis)

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8 pages, 1433 KiB

Open AccessShort Note

Methyl 6-Benzyl-3-Hydroxy-3,6-Dimethyl-1,2-Dioxane-4-Carboxylate

by Alexandre Benech, Omar Khoumeri, Christophe Curti and Patrice Vanelle

Molbank 2024, 2024(2), M1825; https://doi.org/10.3390/M1825 - 23 May 2024

Viewed by 223

Abstract

Plasmodium falciparum is a fast-evolving parasite responsible for the fatal disease malaria, making it crucial to renew our therapeutic arsenal. Modulating the artemisinin’s endoperoxide pharmacophore is a promising route to synthesizing new antimalarial derivatives. For the first step of our 20 mmol scale [...] Read more.

Plasmodium falciparum is a fast-evolving parasite responsible for the fatal disease malaria, making it crucial to renew our therapeutic arsenal. Modulating the artemisinin’s endoperoxide pharmacophore is a promising route to synthesizing new antimalarial derivatives. For the first step of our 20 mmol scale synthesis, catalyzed by manganese (III) acetylacetonate, we applied the conditions previously described in the literature to one of our low-yielding asymmetrically disubstituted alkenes, (2-methylallyl)benzene. Under conditions designed for alkyl derivatives, manganese (II) and (III) acetate catalyzed its peroxycyclization with methyl 3-oxobutanoate to a 1,2-dioxane ring in the presence of oxygen from air at room temperature with a 36% yield, while an oxygen atmosphere, as described in the literature, decreased the yield to 7%. Finally, under conditions designed for aryl derivatives, the yield was reduced to 30%, showing that methylallyl derivatives have an intermediate reactivity that needs further optimization to produce 1,2-dioxane ring by manganese catalyzation in good yields. This work characterizes the product obtained and discusses the most suitable reaction conditions. Full article

(This article belongs to the Collection Molecules from Catalytic Processes)

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8 pages, 2332 KiB

Open AccessCommunication

(Hetero)Arene Ring-Fused [1,2,4]Triazines

by Mahshid Teymouri, Anna Pietrzak and Paulina Bartos

Molbank 2024, 2024(2), M1824; https://doi.org/10.3390/M1824 - 20 May 2024

Viewed by 286

Abstract

Synthetic access to a five (hetero)arene ring-fused 3-phenyl[1,2,4]triazines is described. The resulting compounds were characterized via ¹H and ¹³C NMR, IR, UV–vis spectroscopy and HRMS. The structure of 3-phenyl[1,2,4]triazino[5,6-c]quinoline was unambiguously confirmed by single crystal XRD. Full article

(This article belongs to the Section Organic Synthesis)

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8 pages, 2707 KiB

Open AccessCommunication

4-(Tris(4-methyl-1H-pyrazol-1-yl)methyl)aniline

by Bradley B. Garrison, Joseph E. Duhamel, Nehemiah Antoine, Steven J. K. Symes, Kyle A. Grice, Colin D. McMillen and Jared A. Pienkos

Molbank 2024, 2024(2), M1823; https://doi.org/10.3390/M1823 - 17 May 2024

Viewed by 538

Abstract

4-(tris(4-methyl-1H-pyrazol-1-yl)methyl)aniline was prepared in a 63% yield utilizing a C–F activation strategy from a mixture of 4-(trifluoromethyl)aniline, 4-methylpyrazole, and KOH in dimethylsulfoxide (DMSO). The identity of the product was confirmed by nuclear magnetic resonance spectroscopy, infrared spectroscopy, mass spectrometry, and single-crystal [...] Read more.

4-(tris(4-methyl-1H-pyrazol-1-yl)methyl)aniline was prepared in a 63% yield utilizing a C–F activation strategy from a mixture of 4-(trifluoromethyl)aniline, 4-methylpyrazole, and KOH in dimethylsulfoxide (DMSO). The identity of the product was confirmed by nuclear magnetic resonance spectroscopy, infrared spectroscopy, mass spectrometry, and single-crystal analysis. An analysis of crystals grown from the layering method (CH₂Cl₂/acetone/pentane) indicated two distinct polymorphs of the title compound. Moreover, density functional theory calculations utilizing the MN15L density functional and the def2-TZVP basis set indicated that 4-(tris(4-methyl-1H-pyrazol-1-yl)methyl)aniline forms with similar energetics to the previously reported unmethylated analog. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

8 pages, 1460 KiB

Open AccessShort Note

11-Hydroxy-7-Methoxy-2,8-Dimethyltetracene-5,12-Dione

by Rishi Vachaspathy Astakala, Gagan Preet, Ahlam Haj Hasan, Ria Desai, Juan A. Asenjo, Barbara Andrews, William T. A. Harrison, Rainer Ebel and Marcel Jaspars

Molbank 2024, 2024(2), M1822; https://doi.org/10.3390/M1822 - 14 May 2024

Viewed by 530

Abstract

Microorganisms are a valuable source of pharmaceutically active chemicals, serving as scaffolds for synthesis as well as lead structures. Investigating novel biomes frequently yields intriguing chemistry; the Atacama Desert in Chile is one such example. This study reports the isolation of a new [...] Read more.

Microorganisms are a valuable source of pharmaceutically active chemicals, serving as scaffolds for synthesis as well as lead structures. Investigating novel biomes frequently yields intriguing chemistry; the Atacama Desert in Chile is one such example. This study reports the isolation of a new reduced anthracycline-related compound from the Atacama Desert-derived bacterium Saccharothrix S26. Structural characterisation was achieved by one-dimensional and two-dimensional NMR, HR-LCMS, and X-ray crystallography. The compound was tested against the ESKAPE pathogens, bovine mastitis-related pathogens, and the fungal strain Cryptococcus neoformans, but no antimicrobial activity was observed. Full article

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8 pages, 1286 KiB

Open AccessCommunication

Adamantylated Calix[4]arenes Bearing CuAAC-Ready 2-Azidoethyl or Propargyl Functionalities

by Alexander Gorbunov, Maria Malakhova, Stanislav Bezzubov, Ivan Lentin, Vladimir Kovalev and Ivan Vatsouro

Molbank 2024, 2024(2), M1821; https://doi.org/10.3390/M1821 - 11 May 2024

Viewed by 493

Abstract

1,3-Alternate calix[4]arenes were prepared, having bulky adamantyl groups in the p-positions of all four aromatic units of the macrocycles and pairs of propargyl or 2-azidoethyl groups alternating with n-propyl groups at the phenol oxygen atoms. The step-wise syntheses were carried out [...] Read more.

1,3-Alternate calix[4]arenes were prepared, having bulky adamantyl groups in the p-positions of all four aromatic units of the macrocycles and pairs of propargyl or 2-azidoethyl groups alternating with n-propyl groups at the phenol oxygen atoms. The step-wise syntheses were carried out through a selective distal alkylation of the parent p-adamantylcalix[4]arene with propargyl bromide or 1,2-dibromoethane, resulting in calix[4]arenes bearing pairs of propargyl or 2-bromoethyl groups at their narrow rims. The bromine atoms were replaced by azide groups, and then both calix[4]arene diethers were exhaustively alkylated at the remaining OH-groups with 1-iodopropane under stereoselective conditions to fix the macrocycles in an 1,3-alternate shape. The structures of the prepared p-adamantylcalix[4]arenes were confirmed by NMR and HRMS data, and, for the 1,3-alternate dipropargyl ether, the X-ray diffraction data were also collected. Preliminary data on the reactivity of the prepared calixarenes under the CuAAC conditions suggested a strong steric hampering created by the adamantane units nearby the reacting alkyne or azide groups that affected the outcome of the two-fold cycloaddition involving the calixarene bis(azides) or bis(alkynes) as complementary partners. Full article

(This article belongs to the Section Organic Synthesis)

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6 pages, 663 KiB

Open AccessShort Note

8(S)-[(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyloxy]-3,4-dihydro-2H-[1,4]dithiepino[2,3-c]furan-6(8H)-one

by Alsu M. Khabibrakhmanova, Enze S. Rabbanieva, Darya P. Gerasimova, Liliya Z. Latypova and Almira R. Kurbangalieva

Molbank 2024, 2024(2), M1820; https://doi.org/10.3390/M1820 - 11 May 2024

Viewed by 365

Abstract

The interaction of propane-1,3-dithiol with the chiral bis-thioether, which combines two 2(5H)-furanone moieties, bridged through their carbon atoms C(4) by the propane-1,3-dithiol fragment, in DMF in the presence of potassium hydroxide or cesium carbonate resulted in the formation of an [...] Read more.

The interaction of propane-1,3-dithiol with the chiral bis-thioether, which combines two 2(5H)-furanone moieties, bridged through their carbon atoms C(4) by the propane-1,3-dithiol fragment, in DMF in the presence of potassium hydroxide or cesium carbonate resulted in the formation of an optically active fused bicyclic sulfur heterocycle, possessing 1,4-dithiepine and unsaturated γ-lactone moieties. The studied reaction follows an unexpected pathway in a basic medium with the thiolate–thiolate exchange. The structure of the novel heterocycle of the 1,4-dithiepinofuranone series is characterized by single-crystal X-ray diffraction. Full article

(This article belongs to the Collection Heterocycle Reactions)

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7 pages, 1898 KiB

Open AccessCommunication

Synthesis and Structure of a Coordination Polymer of Ni(II) with 2-(4-Bromophenoxy)acetohydrazide

by Оlena Martsynko, Mariia Nesterkina, Оlena Finik, Kyrylo Tsymbaliuk, Viktoriya Dyakonenko, Svitlana Shishkina and Iryna Kravchenko

Molbank 2024, 2024(2), M1819; https://doi.org/10.3390/M1819 - 8 May 2024

Viewed by 507

Abstract

The coordination compound [NiCl₂L(2-PrOH)]_n (where L is 2-(4-bromophenoxy)acetohydrazide; 2-PrOH is isopropanol) was obtained for the first time. The complex was characterized by means of elemental analyses, molar conductance, thermogravimetric analysis, IR spectroscopy, and single crystal X-ray diffraction analysis. It was [...] Read more.

The coordination compound [NiCl₂L(2-PrOH)]_n (where L is 2-(4-bromophenoxy)acetohydrazide; 2-PrOH is isopropanol) was obtained for the first time. The complex was characterized by means of elemental analyses, molar conductance, thermogravimetric analysis, IR spectroscopy, and single crystal X-ray diffraction analysis. It was determined that the coordination compound exhibits a polymeric structure. The complexing agent is six-coordinated, and its distorted octahedron forms due to the bidentate coordination of 2-(4-bromophenoxy)acetohydrazide through the carbonyl oxygen atom and the amine nitrogen. The oxygen of the molecule of isopropanol, the chlorine atom, and two chlorine atoms serve as bridges between two metal atoms. Full article

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6 pages, 911 KiB

Open AccessShort Note

(E)-1-(5-(Hydroxymethyl) furan-2-yl)-4,4-dimethylpent-1-en-3-one

by Zhongwei Wang, Luxiao Zhou, Peng He and Yukun Qin

Molbank 2024, 2024(2), M1818; https://doi.org/10.3390/M1818 - 7 May 2024

Viewed by 563

Abstract

This study presents a novel approach in the realm of catalytic organic synthesis by integrating biomass catalytic conversion with organic synthesis techniques. Utilizing N-acetylglucosamine as the primary feedstock, the first phase of the research involves its catalytic transformation into 5-hydroxymethylfurfural (HMF). The [...] Read more.

This study presents a novel approach in the realm of catalytic organic synthesis by integrating biomass catalytic conversion with organic synthesis techniques. Utilizing N-acetylglucosamine as the primary feedstock, the first phase of the research involves its catalytic transformation into 5-hydroxymethylfurfural (HMF). The subsequent phase employs a condensation reaction between HMF and 3,3-Dimethyl-2-butanone to synthesize a new compound, (E)-1-(5-(hydroxymethyl) furan-2-yl)-4,4-dimethylpent-1-en-3-one. This two-step process not only demonstrates the feasibility of converting biomass into valuable chemical precursors but also exemplifies the synthesis of novel compounds through green chemistry principles. The successful execution of this methodology offers fresh insights and opens new avenues for advancements in catalytic organic synthesis, emphasizing sustainability and efficiency. Full article

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8 pages, 996 KiB

Open AccessShort Note

4,4’-(Thiophene-2,5-diylbis(ethyne-2,1-diyl))bis(1-methyl-1-pyridinium) Iodide

by Lorenza Romagnoli, Alessandro Latini and Andrea D’Annibale

Molbank 2024, 2024(2), M1817; https://doi.org/10.3390/M1817 - 6 May 2024

Viewed by 514

Abstract

In the vast field of organic functional materials, viologens are widely recognized as an extremely versatile family of substances, due in part to the possibility of extending conjugation between the terminal pyridinium rings, for instance through the insertion of additional aromatic moieties. In [...] Read more.

In the vast field of organic functional materials, viologens are widely recognized as an extremely versatile family of substances, due in part to the possibility of extending conjugation between the terminal pyridinium rings, for instance through the insertion of additional aromatic moieties. In this work, a new, extended viologen with a thiophene core and two acetylene bonds is presented. It was synthesized through a straightforward route, using well-established Sonogashira coupling reactions, and its optical properties were investigated by UV–visible absorption and fluorescence spectroscopy, revealing a very interesting material for diverse fluorescence-related applications. Full article

(This article belongs to the Section Organic Synthesis)

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5 pages, 860 KiB

Open AccessShort Note

Di-µ-(1-(3-(1H-imidazol-1-yl)propyl)-2-methyl-4-oxo-1,4-dihydropyridin-3-olate)-bis[(η⁵-pentamethylcyclopentadienyl)iridium(III)] Chloride

by Ilya A. Shutkov, Nikolai A. Melnichuk, Konstantin A. Lyssenko, Nataliya E. Borisova, Olga N. Kovaleva and Alexey A. Nazarov

Molbank 2024, 2024(2), M1816; https://doi.org/10.3390/M1816 - 5 May 2024

Viewed by 708

Abstract

A metallacyclic maltol-tethered organometallic Ir(III) half-sandwich complex was synthesized as an analog of the ruthenium anticancer complexes (RAPTA/RAED) to evaluate its in vitro antiproliferative activity against various human cancer cell lines. Full article

(This article belongs to the Section Organic Synthesis)

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6 pages, 1019 KiB

Open AccessCommunication

Synthesis and Spectroscopic Study of New 1H-1-Alkyl-6-methyl-7-nitroso-3-phenylpyrazolo[5,1-c][1,2,4]triazoles

by Ion Burcă, Valentin Badea, Vasile-Nicolae Bercean and Francisc Péter

Molbank 2024, 2024(2), M1815; https://doi.org/10.3390/M1815 - 24 Apr 2024

Viewed by 510

Abstract

The nitrosation of 1H-1-alkyl-6-methyl-3-phenylpyrazolo[5,1-c][1,2,4]triazoles leads to new 1H-1-alkyl-6-methyl-7-nitroso-3-phenylpyrazolo[5,1-c][1,2,4] triazoles that react in acidic media, giving rise to 1H-1-alkyl-7-hydroxyimino-6-methyl-3-phenylpyrazolo[5,1-c][1,2,4]triazolium salts. These compounds were characterized by FT-IR, UV-Vis, ¹H-NMR, ¹³C-NMR, and ¹⁵N-NMR spectroscopic techniques. Full article

(This article belongs to the Collection Heterocycle Reactions)

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6 pages, 1469 KiB

Open AccessShort Note

5,6-Diphenyl-1,3,4,7-tetra-p-tolyl-1,3,3a,7a-tetrahydropentaleno[1,2-c]furan

by Shu-Kai Chen, Yi-Hung Liu and Shiuh-Tzung Liu

Molbank 2024, 2024(2), M1814; https://doi.org/10.3390/M1814 - 24 Apr 2024

Viewed by 493

Abstract

The reaction of (Z)-5-phenyl-1,3-di-p-tolylpent-2-en-4-yn-1-ol (1) with trimethylsilyl chloride in dichloromethane at ambient temperature gave a dimeric ether compound 2 in 30% yield. Subsequently, heating 2 in toluene under refluxing temperature rendered the title compound quantitatively. The structure [...] Read more.

The reaction of (Z)-5-phenyl-1,3-di-p-tolylpent-2-en-4-yn-1-ol (1) with trimethylsilyl chloride in dichloromethane at ambient temperature gave a dimeric ether compound 2 in 30% yield. Subsequently, heating 2 in toluene under refluxing temperature rendered the title compound quantitatively. The structure of this tricyclic-fused compound was characterized using NMR, mass spectroscopy, and X-ray crystallography. This unique linear tricyclic fused furan framework is reported for the first time. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

5 pages, 946 KiB

Open AccessShort Note

5,5′-Thiobis(3-bromoisothiazole-4-carbonitrile)

by Andreas S. Kalogirou and Panayiotis A. Koutentis

Molbank 2024, 2024(2), M1813; https://doi.org/10.3390/M1813 - 24 Apr 2024

Viewed by 517

Abstract

The reaction of sodium 2,2-dicyanoethene-1,1-bis(thiolate) with bromine (2 equiv.) in CCl₄ gave 3,5-dibromoisothiazole-3-carbonitrile and 5,5′-thiobis(3-bromoisothiazole-4-carbonitrile) in 7% and 18% yields, respectively. The latter novel compound was fully characterized. Full article

(This article belongs to the Section Organic Synthesis)

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8 pages, 1315 KiB

Open AccessShort Note

2S-(1RS-benzyloxy-hex-5-enyl)-2,3-dihydro-1,4-benzodioxine

by Angelica Artasensi and Laura Fumagalli

Molbank 2024, 2024(2), M1812; https://doi.org/10.3390/M1812 - 24 Apr 2024

Viewed by 617

Abstract

In medicinal chemistry, the precise configuration of molecules is a crucial determinant of their pharmacological properties. Hence, the introduction of a new chiral center during the synthetic pathway involves the assignment of configuration. Herein we assign, by means of molecular modeling ¹H [...] Read more.

In medicinal chemistry, the precise configuration of molecules is a crucial determinant of their pharmacological properties. Hence, the introduction of a new chiral center during the synthetic pathway involves the assignment of configuration. Herein we assign, by means of molecular modeling ¹H and 2D Nuclear Overhauser Effect NMR techniques, the configuration of the two diastereomers 2S-(1R-benzyloxy-hex-5-enyl)-2,3-dihydro-1,4-benzodioxine and 2S-(1S-benzyloxy-hex-5-enyl)-2,3-dihydro-1,4-benzodioxine, which are useful to synthetize analogs of the potent and highly selective dipeptidyl peptidase IV and carbonic anhydrase inhibitor recently published. Full article

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5 pages, 552 KiB

Open AccessShort Note

Chloro(η²,η²-cycloocta-1,5-diene){1-benzyl-3-[(S)-2-hydroxy-1-methylethyl]benzimidazol-2-ylidene}rhodium(I)

by Satoshi Sakaguchi and Shogo Matsuo

Molbank 2024, 2024(2), M1811; https://doi.org/10.3390/M1811 - 19 Apr 2024

Viewed by 502

Abstract

Previously, we demonstrated the synthesis of a well-defined hydroxyalkyl-functionalized N-heterocyclic carbene (NHC)/Ru(II) complex through the transmetalation reaction between [RuCl₂(p-cymene)]₂ and the corresponding NHC/Ag(I) complex derived from a chiral benzimidazolium salt using the Ag₂O method. In [...] Read more.

Previously, we demonstrated the synthesis of a well-defined hydroxyalkyl-functionalized N-heterocyclic carbene (NHC)/Ru(II) complex through the transmetalation reaction between [RuCl₂(p-cymene)]₂ and the corresponding NHC/Ag(I) complex derived from a chiral benzimidazolium salt using the Ag₂O method. In this study, we successfully synthesized [RhX(cod)(NHC)] complexes through a one-pot deprotonation route. The hydroxyalkyl-substituted benzimidazolium salt reacted with [Rh(OH)(cod)]₂ in THF at room temperature, affording the corresponding monodentate NHC/Rh(I) complex in nearly quantitative yield. The rhodium complex was characterized using NMR, HRMS measurement, and elemental analysis. Full article

(This article belongs to the Topic Heterocyclic Carbene Catalysis)

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5 pages, 640 KiB

Open AccessShort Note

Chloro(η²,η²-cycloocta-1,5-diene){1-[(2-[(S)-1-(hydroxymethyl)-3-methylbutyl]amino)-2-oxoethyl]-3-(1-naphthalenylmethyl)benzimidazol-2-ylidene}rhodium(I)

by Satoshi Sakaguchi and Shogo Matsuo

Molbank 2024, 2024(2), M1810; https://doi.org/10.3390/M1810 - 19 Apr 2024

Viewed by 545

Abstract

Commercially available and air- and moisture-stable rhodium complex [Rh(OH)(cod)]₂ (2) was utilized in the synthesis of [RhX(cod)(NHC)] (3). The presence of an OH group in complex 2 serves as an internal base, facilitating the deprotonation of the C–H [...] Read more.

Commercially available and air- and moisture-stable rhodium complex [Rh(OH)(cod)]₂ (2) was utilized in the synthesis of [RhX(cod)(NHC)] (3). The presence of an OH group in complex 2 serves as an internal base, facilitating the deprotonation of the C–H bond of the azolium ring in the hydroxyamide-substituted benzimidazolium salt 1. This reaction between 1 and 2 proceeded in THF at room temperature without temperature control, affording the desired NHC/Rh complex 3 in excellent yield. The characterization of complex 3 was accomplished through NMR and HRMS analyses, revealing its existence as a diastereomeric mixture of two NHC/Rh complexes. Furthermore, its catalytic performance was briefly evaluated in the reaction between 2-naphthaldehyde (5) and phenylboronic acid (6). Full article

(This article belongs to the Topic Heterocyclic Carbene Catalysis)

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4 pages, 656 KiB

Open AccessShort Note

1-(3-Chlorophenyl)-3-(6-((1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)hexyl)thiourea

by Daria Zapravdina and Vladimir Burmistrov

Molbank 2024, 2024(2), M1809; https://doi.org/10.3390/M1809 - 18 Apr 2024

Viewed by 548

Abstract

The compound 1-(3-chlorophenyl)-3-(6-((1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)hexyl)thiourea was synthesized for the first time from 6-((1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)hexan-1-amine and 3-chlorophenylisothiocyanate in DMF with a 60% yield. It was characterized by ¹H, ¹³C{¹H} NMR, FT-IR, MS, and elemental analysis. Full article

(This article belongs to the Section Organic Synthesis)

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7 pages, 1059 KiB

Open AccessShort Note

Diiodido-bis{N-[2-(diphenylphosphino)benzylidene]benzylamine-κ²N,P}dicopper(I)

by Julian Süß, Uwe Monkowius and Manfred Zabel

Molbank 2024, 2024(2), M1808; https://doi.org/10.3390/M1808 - 18 Apr 2024

Viewed by 582

Abstract

The one-pot template reaction between 2-(diphenylphosphino)benzaldehyde, benzylamine and copper(I) iodide yields the dinuclear copper complex (P∩N)₂Cu₂I₂, as revealed by single-crystal X-ray diffraction. Full article

(This article belongs to the Section Structure Determination)

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6 pages, 1274 KiB

Open AccessShort Note

3,3’-(4,11-Bis(4-(trifluoromethyl)benzyl)-1,4,8,11-Tetraazacyclotetradecane-1,8-diyl)dipropanenitrile

by Inês M. Nunes, Elisabete R. Silva and Luis G. Alves

Molbank 2024, 2024(2), M1807; https://doi.org/10.3390/M1807 - 17 Apr 2024

Viewed by 615

Abstract

The cyclam derivative (NCCH₂CH₂)₂(^4-CF3PhCH₂)₂Cyclam was prepared by the reaction of H₂(^4-CF3PhCH₂)₂Cyclam with acrylonitrile in methanol. The compound was fully characterized by elemental analysis, [...] Read more.

The cyclam derivative (NCCH₂CH₂)₂(^4-CF3PhCH₂)₂Cyclam was prepared by the reaction of H₂(^4-CF3PhCH₂)₂Cyclam with acrylonitrile in methanol. The compound was fully characterized by elemental analysis, mass spectrometry as well as IR and NMR spectroscopy. Crystals of (NCCH₂CH₂)₂(^4-CF3PhCH₂)₂Cyclam suitable for single-crystal X-ray diffraction were obtained by the slow evaporation of a chloroform solution of the compound. The establishment of non-classical hydrogen bonds and unusual nitrile–nitrile and π(CN)^…π interactions determined the solid-state supramolecular architecture of (NCCH₂CH₂)₂(^4-CF3PhCH₂)₂Cyclam. Full article

(This article belongs to the Section Structure Determination)

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6 pages, 954 KiB

Open AccessCommunication

Synthesis and Analytical Characterization of Cyclization Products of 3-Propargyloxy-5-benzyloxy-benzoic Acid Methyl Ester

by Matteo Mori, Giulia Cazzaniga, Donatella Nava and Elena Pini

Molbank 2024, 2024(2), M1806; https://doi.org/10.3390/M1806 - 16 Apr 2024

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Abstract

In the context of our ongoing studies on chromane derivatives as inhibitors of the salicylate synthase from M. tuberculosis, we isolated a new, unexpected compound from the cyclization of 3-(propargyloxy)-5-benzyloxy-benzoic acid methyl ester. Its molecular structure was elucidated by means of 1D [...] Read more.

In the context of our ongoing studies on chromane derivatives as inhibitors of the salicylate synthase from M. tuberculosis, we isolated a new, unexpected compound from the cyclization of 3-(propargyloxy)-5-benzyloxy-benzoic acid methyl ester. Its molecular structure was elucidated by means of 1D and 2D NMR analyses, FT-IR, ESI-MS, and HRMS. Full article

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

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7 pages, 4214 KiB

Open AccessCommunication

The Synthesis and Structure of Scandium Dichloride of Sterically Demanding Aminopyridinato Ligands

by Sadaf Qayyum

Molbank 2024, 2024(2), M1805; https://doi.org/10.3390/M1805 - 10 Apr 2024

Viewed by 750

Abstract

The reaction of the potassium salt of (2,6-diisopropylphenyl)-[6-(2,4,6-triisopropylphenyl)-pyridine-2-yl]-amine (Ap*H) with the equimolar ratio of [ScCl₃] in tetrahydrofuran (thf) resulted in the mononuclear mono(aminopyridinato) scandium dichloride complex [Ap*ScCl₂(thf)₂]. An X-ray analysis showed the title compound to be monomeric. [...] Read more.

The reaction of the potassium salt of (2,6-diisopropylphenyl)-[6-(2,4,6-triisopropylphenyl)-pyridine-2-yl]-amine (Ap*H) with the equimolar ratio of [ScCl₃] in tetrahydrofuran (thf) resulted in the mononuclear mono(aminopyridinato) scandium dichloride complex [Ap*ScCl₂(thf)₂]. An X-ray analysis showed the title compound to be monomeric. The compound [C₄₀H₅₉Cl₂N₂O₂Sc] crystallized in the monoclinic space group, P2₁/n, and possessed the following cell parameters: a = 12.4441(8) b = 22.9975(10) c = 13.9971(8) Å, β = 92.297(5)°, V = 4002.5(4) A³, and Z = 4. Hirshfeld analyses show that H…H (91.1%), H…C/C…H (5.0%), and H…Cl/Cl…H (3.9%) are the contributing interactions in the solid-state structure. The compound was further characterized by NMR spectroscopy, and its purity was confirmed by elemental analysis. Full article

(This article belongs to the Section Structure Determination)

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6 pages, 382 KiB

Open AccessShort Note

1,2-Dibenzoylthiosemicarbazide

by Burcă Ion, Badea Valentin, Todea Anamaria and Bercean Vasile-Nicolae

Molbank 2024, 2024(2), M1804; https://doi.org/10.3390/M1804 - 9 Apr 2024

Viewed by 582

Abstract

When 1-benzoylthiosemicarbazide (2) or thiosemicarbazide (1) were treated with benzoyl chloride in a basic medium, a mixture of two compounds was obtained: 1,2-dibenzoylthiosemicarbazide (3) and 1,4-dibenzoylthiosemicarbazide (4). To determine the structure of the novel compounds, [...] Read more.

When 1-benzoylthiosemicarbazide (2) or thiosemicarbazide (1) were treated with benzoyl chloride in a basic medium, a mixture of two compounds was obtained: 1,2-dibenzoylthiosemicarbazide (3) and 1,4-dibenzoylthiosemicarbazide (4). To determine the structure of the novel compounds, 2D NMR spectroscopy techniques such as ¹H-¹³C and ¹H-¹⁵N were employed. Full article

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

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6 pages, 2425 KiB

Open AccessShort Note

Benzo[d][1,2,3]oxadithiole 2-Oxide

by R. Alan Aitken, David B. Cordes, Arun Goyal and Aidan P. McKay

Molbank 2024, 2024(2), M1803; https://doi.org/10.3390/M1803 - 7 Apr 2024

Viewed by 803

Abstract

A simplified synthesis of the title compound is reported and its ¹H and ¹³C NMR data are fully assigned including determination of H–H and C–H coupling constants. Its X-ray structure has been determined for the first time. NMR data are also [...] Read more.

A simplified synthesis of the title compound is reported and its ¹H and ¹³C NMR data are fully assigned including determination of H–H and C–H coupling constants. Its X-ray structure has been determined for the first time. NMR data are also presented for the oxygen analogue. Full article

(This article belongs to the Section Structure Determination)

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5 pages, 620 KiB

Open AccessShort Note

N-(3-chlorophenethyl)-4-nitrobenzamide

by Diyana Dimitrova, Stanimir Manolov, Dimitar Bojilov, Iliyan Ivanov and Paraskev Nedialkov

Molbank 2024, 2024(2), M1802; https://doi.org/10.3390/M1802 - 1 Apr 2024

Viewed by 1374

Abstract

Herein, we report the synthesis of N-(3-chlorophenethyl)-4-nitrobenzamide in the reaction between 2-(3-chlorophenyl)ethan-1-amine and 4-nitrobenzoyl chloride. The newly obtained bio-functional hybrid molecule was fully characterized via ¹H, ¹³C NMR, UV, and mass spectral data. Full article

(This article belongs to the Section Structure Determination)

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6 pages, 1182 KiB

Open AccessShort Note

1,4-Diiodotetrafluorobenzene 3,5-di-(pyridin-4-yl)-1,2,4-thiadiazole <1/1>

by Enrico Podda, Anna Pintus, Vito Lippolis, Francesco Isaia, Alexandra M. Z. Slawin, Cameron L. Carpenter-Warren, John Derek Woollins and Maria Carla Aragoni

Molbank 2024, 2024(2), M1801; https://doi.org/10.3390/M1801 - 1 Apr 2024

Viewed by 674

Abstract

The reactivity of 3,5-di-(pyridin-4-yl)-1,2,4-thiadiazole (L1) with 1,4-diiodotetrafluorobenzene (1,4-DITFB) was explored and the halogen-bonded 1:1 co-crystal (1) was successfully isolated and structurally characterized. Full article

(This article belongs to the Section Structure Determination)

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9 pages, 1518 KiB

Open AccessShort Note

(2R,4aS,6aS,12bR,14aS,14bR)-N-(2-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy)ethyl)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxamide

by Guo Yuzhu, Margrate Anyanwu, Xiao Yang, Ren Zimo, Alessandra Gianoncelli, Giovanni Ribaudo and Paolo Coghi

Molbank 2024, 2024(2), M1800; https://doi.org/10.3390/M1800 - 1 Apr 2024

Viewed by 751

Abstract

In this report, we discuss the synthesis of a compound obtained from the derivatization of the natural compound celastrol. This derivative is connected to PEG azide moiety through an amide linkage. The linkage was achieved through the activation of the carboxylic acid using [...] Read more.

In this report, we discuss the synthesis of a compound obtained from the derivatization of the natural compound celastrol. This derivative is connected to PEG azide moiety through an amide linkage. The linkage was achieved through the activation of the carboxylic acid using HOBt/EDC. The compound was fully characterized by proton (¹H), carbon-13 (¹³C), heteronuclear single quantum coherence (HSQC), correlation spectroscopy (¹H-¹H-COSY), and distortionless enhancement by polarization transfer (DEPT) NMR. Ultraviolet (UV), Fourier-transform infrared (FTIR), and high-resolution mass spectrometry (HRMS) were also adopted. Computational investigations were conducted to forecast the binding mode between the synthesized compound and sarco-endoplasmic reticulum (SR) Ca2+ transport ATPase (SERCA), a known target for the development of novel therapeutics for rheumatoid arthritis. Additionally, the drug-likeness of the synthesized compound was assessed by predicting its pharmacokinetic properties. Full article

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Molbank, Volume 2024, Issue 2 (June 2024) – 33 articles

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