Molbank

10 pages, 3408 KiB

Open AccessCommunication

Synthesis of N-p-Fluorothiosemicarbazone and of Bis(N-p-Fluorophenylthiourea): Crystal Structure and Conformational Analysis of N,N′-Bis(4-Fluorophenyl)Hydrazine-1,2-Bis(Carbothioamide)

by Sirine Salhi, Dorra Kanzari-Mnallah, Isabelle Jourdain, Michael Knorr, Carsten Strohmann, Jan-Lukas Kirchhoff, Hédi Mrabet and Azaiez Ben Akacha

Molbank 2024, 2024(4), M1926; https://doi.org/10.3390/M1926 - 28 Nov 2024

Abstract

The reaction of the phosphonated hydrazone (2-hydrazineylidenepropyl) diphenylphosphine oxide 1 with p-fluorophenyl-isothiocyanate yields as a major product the thiosemicarbazone Ph₂P(=O)CH₂{C=N-NH(C=S)-N(H)C₆H₄F}CH₃ (2-(1-(diphenylphosphoryl)propan-2-ylidene)-N-(4-fluorophenyl)hydrazine-1-carbothioamide) 2 along with bis(N-p-fluorophenylthiourea) 3 as [...] Read more.

The reaction of the phosphonated hydrazone (2-hydrazineylidenepropyl) diphenylphosphine oxide 1 with p-fluorophenyl-isothiocyanate yields as a major product the thiosemicarbazone Ph₂P(=O)CH₂{C=N-NH(C=S)-N(H)C₆H₄F}CH₃ (2-(1-(diphenylphosphoryl)propan-2-ylidene)-N-(4-fluorophenyl)hydrazine-1-carbothioamide) 2 along with bis(N-p-fluorophenylthiourea) 3 as a minor product. The latter compound 3 was isolated as the main product by direct treatment of p-FC₆H₄N=C=S with hydrazine in a 2:1 ratio. Both 2 and 3 were characterized by NMR. Furthermore, the molecular structure of 3 was elucidated by an X-ray diffraction study, revealing both intra- and intermolecular secondary interactions. A conformational DFT study, at the B3LYP/6-311 G++ (d, p) level of theory, confirms a good match between the calculated structure and the experimental one. Full article

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

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6 pages, 1298 KiB

Open AccessShort Note

2-([1,1′-Biphenyl]-4-yl)-5-[(E)-2-(3-methoxy-1-phenyl-1H-pyrazol-4-yl)ethenyl]-3,3-dimethyl-3H-indole

by Gabrielė Varvuolytė, Aurimas Bieliauskas, Neringa Kleizienė, Asta Žukauskaitė and Algirdas Šačkus

Molbank 2024, 2024(4), M1927; https://doi.org/10.3390/M1927 - 28 Nov 2024

Abstract

The ligandless palladium-catalyzed Heck reaction of 4-ethenyl-3-methoxy-1-phenyl-1H-pyrazole and 2-([1,1′-biphenyl]-4-yl)-5-bromo-3,3-dimethyl-3H-indole gave the previously unreported 2-([1,1′-biphenyl]-4-yl)-5-[(E)-2-(3-methoxy-1-phenyl-1H-pyrazol-4-yl)ethenyl]-3,3-dimethyl-3H-indole in 45% yield. The compound was characterized using NMR, FT-IR spectroscopy, and HRMS data. The optical properties of the [...] Read more.

The ligandless palladium-catalyzed Heck reaction of 4-ethenyl-3-methoxy-1-phenyl-1H-pyrazole and 2-([1,1′-biphenyl]-4-yl)-5-bromo-3,3-dimethyl-3H-indole gave the previously unreported 2-([1,1′-biphenyl]-4-yl)-5-[(E)-2-(3-methoxy-1-phenyl-1H-pyrazol-4-yl)ethenyl]-3,3-dimethyl-3H-indole in 45% yield. The compound was characterized using NMR, FT-IR spectroscopy, and HRMS data. The optical properties of the compound were investigated in tetrahydrofuran by UV-Vis and fluorescence spectroscopy. Full article

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

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5 pages, 913 KiB

Open AccessCommunication

3-Methyl-2-(5-((trimethylsilyl)ethynyl)pyridin-2-yl)butan-2-ol

by Oleg A. Mikhailov, Almira R. Kurbangalieva and Ilya D. Gridnev

Molbank 2024, 2024(4), M1925; https://doi.org/10.3390/M1925 - 27 Nov 2024

Abstract

The reactions of dialkylzinc reagents with ketones are scarcely studied. In this paper, we describe a previously unknown direct alkylation of substituted 2-acetylpyridine with diisopropyl zinc, which gave a corresponding novel alcohol with 82% yield. Full article

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

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Scheme 1

7 pages, 1667 KiB

Open AccessShort Note

Ammonium Oxathioamidate

by M. Carla Aragoni, David B. Cordes, Anna Pintus, Enrico Podda, Riccardo Serra, Alexandra M. Z. Slawin, J. Derek Woollins and Massimiliano Arca

Molbank 2024, 2024(4), M1924; https://doi.org/10.3390/M1924 - 26 Nov 2024

Abstract

Ammonium oxathioamidate (1) was synthesised by the reaction between O-ethyl-thioxamate (oxalic acid-1-amide-2-O-ethyl ester) and ammonium hydrogen carbonate in water solution. Compound 1 was fully characterised by both microanalytical (elemental analysis, melting point determination) and spectroscopic means (FT-IR and [...] Read more.

Ammonium oxathioamidate (1) was synthesised by the reaction between O-ethyl-thioxamate (oxalic acid-1-amide-2-O-ethyl ester) and ammonium hydrogen carbonate in water solution. Compound 1 was fully characterised by both microanalytical (elemental analysis, melting point determination) and spectroscopic means (FT-IR and NMR spectroscopy). Crystals suitable for single-crystal X-ray diffraction were isolated by slow evaporation of an ethanol solution of the compound. The analysis of the crystal packing reveals the prominent role exerted by intermolecular hydrogen bonding (HB) and chalcogen bonding (ChB) interactions. Full article

(This article belongs to the Section Structure Determination)

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8 pages, 2827 KiB

Open AccessCommunication

Coordination of O-Propyl-N-phenylthiocarbamate to HgI₂ and the Crystallographic Characterization of an Anilinium Chloride Thiocarbamate Adduct

by Wafa Arar, Nuri Ekici, Michael Knorr, Isabelle Jourdain, Carsten Strohmann and Jan-Lukas Kirchhoff

Molbank 2024, 2024(4), M1923; https://doi.org/10.3390/M1923 - 22 Nov 2024

Abstract

In order to investigate the coordination chemistry of O-alkyl N-aryl thiocarbamate ligands, HgI₂ was reacted with one equivalent of PrOC(=S)N(H)Ph L in toluene solution to afford the 1D polymeric title compound [{IHg(μ-I)}{κ¹-PrOC(=S)N(H)Ph}]_n CP1. The formation [...] Read more.

In order to investigate the coordination chemistry of O-alkyl N-aryl thiocarbamate ligands, HgI₂ was reacted with one equivalent of PrOC(=S)N(H)Ph L in toluene solution to afford the 1D polymeric title compound [{IHg(μ-I)}{κ¹-PrOC(=S)N(H)Ph}]_n CP1. The formation of this iodide-bridged coordination polymer was ascertained by a single-crystal X-ray diffraction study performed at 100 K, as well as the formation of an adduct between anilinium chloride and L forming a supramolecular ribbon of composition [L(PhNH₃)(Cl)]. The occurrence of anilinium chloride is due to the partial hydrolysis of L in the presence of HCl. Full article

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

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8 pages, 2407 KiB

Open AccessShort Note

6,8-Dibromo-11H-indeno[1,2-b]quinolin-11-one

by Anastasia R. Kovrizhina, Dauren Tolegen, Dmitry I. Pavlov, Andrei S. Potapov and Andrei I. Khlebnikov

Molbank 2024, 2024(4), M1922; https://doi.org/10.3390/M1922 - 21 Nov 2024

Abstract

We report the synthesis of the new compound 6,8-dibromo-11H-indeno[1,2-b]quinolin-11-one, which presents an important type of nitrogen-containing heterocycles and is a useful intermediate product in organic synthesis. The structure of the compound was confirmed by the single crystal X-ray diffraction. [...] Read more.

We report the synthesis of the new compound 6,8-dibromo-11H-indeno[1,2-b]quinolin-11-one, which presents an important type of nitrogen-containing heterocycles and is a useful intermediate product in organic synthesis. The structure of the compound was confirmed by the single crystal X-ray diffraction. Molecular docking analysis revealed that 6,8-dibromo-11H-indeno[1,2-b]quinolin-11-one may effectively intercalate with DNA. The synthesized indenoquinoline derivative thus represents a promising lead compound for developing targeted anticancer and anti-inflammatory drugs. Full article

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5 pages, 824 KiB

Open AccessShort Note

Cyclo[Tri(thiomethyl-1,2-phenylmethylene)]

by Pablo Simón Marqués, Nicolas Bréfuel and Claire Kammerer

Molbank 2024, 2024(4), M1921; https://doi.org/10.3390/M1921 - 21 Nov 2024

Abstract

During the purification of a reported compound named 1,3-dihydrobenzo[c]thiophene, we isolated an unexpected molecule in one of the chromatography fractions by serendipity. Structural elucidation using common techniques such as 1D and 2D NMR, and mass spectrometry revealed the nature of this [...] Read more.

During the purification of a reported compound named 1,3-dihydrobenzo[c]thiophene, we isolated an unexpected molecule in one of the chromatography fractions by serendipity. Structural elucidation using common techniques such as 1D and 2D NMR, and mass spectrometry revealed the nature of this novel product characterized as cyclo[tri(thiomethyl-1,2-phenylmethylene)]. Full article

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

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4 pages, 611 KiB

Open AccessShort Note

trans-11-(3,4-Dimethoxyphenyl)-2,3,8,9-tetramethoxy-6-oxo-11,12-dihydro-6H-dibenzo[c,h]chromene-12-carboxylic Acid

by Victor Angelov, Savina Stoyanova and Milen G. Bogdanov

Molbank 2024, 2024(4), M1920; https://doi.org/10.3390/M1920 - 19 Nov 2024

Abstract

The title compound, trans-11-(3,4-Dimethoxyphenyl)-2,3,8,9-tetramethoxy-6-oxo-11,12-dihydro-6H-dibenzo[c,h]chromene-12-carboxylic acid (4), was synthesized for the first time via a two-step protocol from 3,4-dimethoxyhomophthalic anhydride (1) and 3,4-dimethoxybenzaldehyde (DMBA). In the first step, 1 reacts with DMBA to give [...] Read more.

The title compound, trans-11-(3,4-Dimethoxyphenyl)-2,3,8,9-tetramethoxy-6-oxo-11,12-dihydro-6H-dibenzo[c,h]chromene-12-carboxylic acid (4), was synthesized for the first time via a two-step protocol from 3,4-dimethoxyhomophthalic anhydride (1) and 3,4-dimethoxybenzaldehyde (DMBA). In the first step, 1 reacts with DMBA to give trans-3-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1-oxo-3,4-dihydro-1H-2-benzopyran-4-carboxylic acid (2), which further reacts with two additional equivalents of 1 to give 4. Compound 4 was characterized by means of spectral methods—¹H-, ¹³C-, DEPT-135-NMR, and HRMS. Full article

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5 pages, 952 KiB

Open AccessShort Note

5,5’-Selenobis(1-benzyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde)

by Emeline Grosjean, Julien Rizet, Shekoufeh Arabi Aliabadi, Joelle Azéma-Despeyroux, Pascal Hoffmann and Christian Lherbet

Molbank 2024, 2024(4), M1919; https://doi.org/10.3390/M1919 - 18 Nov 2024

Abstract

Selenium compounds have garnered significant attention in the field of medicinal chemistry due to their unique biochemical properties and potential therapeutic applications for different pathologies. In this study, we report the synthesis of a new selenylated bis-pyridone compound using SeO₂ as the [...] Read more.

Selenium compounds have garnered significant attention in the field of medicinal chemistry due to their unique biochemical properties and potential therapeutic applications for different pathologies. In this study, we report the synthesis of a new selenylated bis-pyridone compound using SeO₂ as the source of selenium. Detailed ¹H and ¹³C NMR characterizations and mass spectral analysis are given. Full article

(This article belongs to the Collection Heterocycle Reactions)

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8 pages, 651 KiB

Open AccessCommunication

A Gram Scale Synthesis of 3,4-Dihalogen Substituted 1,8-Naphthalimides

by Denitsa Anastasova, Monika Mutovska, Natali Simeonova, Irena Zagranyarska, Zlatina Vlahova, Stanimir Stoyanov and Yulian Zagranyarski

Molbank 2024, 2024(4), M1918; https://doi.org/10.3390/M1918 - 18 Nov 2024

Abstract

A general protocol for the synthesis of 3,4-dihalogen substituted 1,8-naphthalimides is proposed, starting from available and cheap 1,8-naphthalic anhydride. The reported new compounds have only bromine or chlorine atoms as substituents, in contrast to the known iodo-containing analogues. This is an advantage in [...] Read more.

A general protocol for the synthesis of 3,4-dihalogen substituted 1,8-naphthalimides is proposed, starting from available and cheap 1,8-naphthalic anhydride. The reported new compounds have only bromine or chlorine atoms as substituents, in contrast to the known iodo-containing analogues. This is an advantage in possible aryl nucleophilic substitution or cross-coupling modifications, making them interesting and important building-block molecules in naphthalimide chemistry. Although the procedure includes five synthetic steps, they are quick and straightforward. The overall yields are relatively high (48–62%), and only one column of chromatographic purification is needed. All the reactions were carried out on a multigram scale to allow the target building-block compounds to be obtained in sufficient amounts for further derivatizations. Full article

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

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Graphical abstract

6 pages, 1811 KiB

Open AccessShort Note

9,10-Bis(5H-dibenzo[b,f]azepino)anthracene

by Himeko Kawaguchi and Takuya Kuwabara

Molbank 2024, 2024(4), M1917; https://doi.org/10.3390/M1917 - 15 Nov 2024

Abstract

The title compound with a donor–π–donor (D–π–D) type triad structure was synthesized by Buchwald–Hartwig amination using 9,10-dibromoanthracene and 5H-dibenzo[b,f]azepine, and characterized by ¹H, ¹³C{¹H} NMR, HRMS, and X-ray diffraction analysis. The azepine–anthracene–azepine units [...] Read more.

The title compound with a donor–π–donor (D–π–D) type triad structure was synthesized by Buchwald–Hartwig amination using 9,10-dibromoanthracene and 5H-dibenzo[b,f]azepine, and characterized by ¹H, ¹³C{¹H} NMR, HRMS, and X-ray diffraction analysis. The azepine–anthracene–azepine units are nearly orthogonal to each other, with a torsion angle of 88°. A broad and weak absorption band around 410–480 nm and the low emission character (Φ_F = 0.01) suggest the weak intramolecular charge transfer from the azepine to the anthracene unit due to the twisted structure. Full article

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

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7 pages, 303 KiB

Open AccessShort Note

2,2^′-[2,4-Bis(4-chlorophenyl)cyclobutane-1,3-diyl]bis(8-bromo-6-chloro-3-nitroimidazo[1,2-a]pyridine)

by Inès Jacquet, Romain Paoli-Lombardo, Caroline Castera-Ducros, Patrice Vanelle and Nicolas Primas

Molbank 2024, 2024(4), M1916; https://doi.org/10.3390/M1916 - 14 Nov 2024

Abstract

In the context of our ongoing studies on 3-nitroimidazo[1,2-a]pyridine derivatives as potent antileishmanial compounds, we isolated a new unexpected compound from the spontaneous cycloaddition of N-[2-(8-bromo-6-chloro-3-nitroimidazo[1,2-a]pyridin-2-yl)-1-(4-chlorophenyl)ethyl]-4-methylbenzenesulfonamide. The molecular structure was fully characterized by using ¹H and ¹³C NMR, X-ray crystallography, and HRMS. Full article

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6 pages, 725 KiB

Open AccessCommunication

Water-Mediated Synthesis of (E)-3-(1-Methyl-1H-benzo[d]imidazol-5-yl)-N-phenethylacrylamide, a Caffeic Acid Phenethyl Amide Analogue

by Muppidi Subbarao and Sean M. Kerwin

Molbank 2024, 2024(4), M1915; https://doi.org/10.3390/M1915 - 12 Nov 2024

Abstract

Caffeic acid phenethyl ester (CAPE) is a phenolic natural product with diverse biological activities, notably anticancer properties. However, its ester group is metabolically unstable. The amide derivative, CAPA, offers improved metabolic stability to esterases but still possesses a metabolically liable catechol group. In [...] Read more.

Caffeic acid phenethyl ester (CAPE) is a phenolic natural product with diverse biological activities, notably anticancer properties. However, its ester group is metabolically unstable. The amide derivative, CAPA, offers improved metabolic stability to esterases but still possesses a metabolically liable catechol group. In this work, we describe the synthesis of a novel CAPA analogue in which the catechol is replaced with a benzimidazole bioisostere via a water-mediated Wittig reaction. Full article

(This article belongs to the Section Natural Product Chemistry)

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Graphical abstract

9 pages, 1166 KiB

Open AccessCommunication

One Pot Synthesis of New Powerful Building Blocks in 1,8-Naphthalimide Chemistry

by Monika Mutovska, Denitsa Anastasova, Natali Simeonova, Irena Zagranyarska, Zlatina Vlahova, Iva Ugrinova, Stanimir Stoyanov and Yulian Zagranyarski

Molbank 2024, 2024(4), M1914; https://doi.org/10.3390/M1914 - 11 Nov 2024

Abstract

This communication reports a reliable one-pot synthetic protocol for preparation on a multigram scale of 3-bromo- and 3,4-dibromo-6-nitro-1,8-naphthalic anhydride from commercially available and economical 1,8-naphthalic anhydride. The synthetic steps used were nitration and selective bromination in sulfuric acid at room temperature. The reaction [...] Read more.

This communication reports a reliable one-pot synthetic protocol for preparation on a multigram scale of 3-bromo- and 3,4-dibromo-6-nitro-1,8-naphthalic anhydride from commercially available and economical 1,8-naphthalic anhydride. The synthetic steps used were nitration and selective bromination in sulfuric acid at room temperature. The reaction takes place under mild conditions and is completely controllable depending on the equivalents of the brominating reagent used. Both anhydrides are powerful building blocks in naphthalimide chemistry. In addition, their imides and esters were also synthesized. Full article

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

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5 pages, 1563 KiB

Open AccessShort Note

Dichloro-bis[(Z)-1-styryl-benzimidazole]-zinc(II)

by Neslihan Şahin, İsmail Özdemir and David Sémeril

Molbank 2024, 2024(4), M1913; https://doi.org/10.3390/M1913 - 5 Nov 2024

Abstract

We have successfully synthesized the dichloro-bis[(Z)-1-styryl-benzimidazole]-zinc(II) complex, which was fully characterized by IR, elemental analysis, and mass and NMR spectroscopy. The solid-state structure definitively shows that two benzimidazole moieties are coordinated to the zinc atom, which adopts a tetrahedral geometry. Full article

(This article belongs to the Section Structure Determination)

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5 pages, 1032 KiB

Open AccessCommunication

Synthesis of 1,2,4-Oxadiazoles Based on Diffractaic Acid

by Aleksandr Filimonov, Anastasia Diveikina, Yuri Gatilov, Olga Luzina and Nariman Salakhutdinov

Molbank 2024, 2024(4), M1912; https://doi.org/10.3390/M1912 - 1 Nov 2024

Abstract

Diffractic acid 1 is a secondary metabolite of depside lichens with antibacterial and insecticidal properties, and anticancer, hepatoprotective and antiviral activities. Novel diffractaic acid derivatives containing a 1,2,4-oxadiazole ring with an aryl substituent have been synthesized by the reaction of diffractaic acid with [...] Read more.

Diffractic acid 1 is a secondary metabolite of depside lichens with antibacterial and insecticidal properties, and anticancer, hepatoprotective and antiviral activities. Novel diffractaic acid derivatives containing a 1,2,4-oxadiazole ring with an aryl substituent have been synthesized by the reaction of diffractaic acid with amidoximes. Full article

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5 pages, 1162 KiB

Open AccessShort Note

Dichloro-Bis(1-cinnamyl-benzimidazole)-Cobalt(II)

by Neslihan Şahin, İsmail Özdemir and David Sémeril

Molbank 2024, 2024(4), M1911; https://doi.org/10.3390/M1911 - 31 Oct 2024

Abstract

Dichloro-bis(1-cinnamyl-benzimidazole)-cobalt(II) was prepared in one step using a cobalt precursor CoCl₂ and corresponding substituted benzimidazole. The complex was fully characterized using IR, elemental analysis, and mass- and NMR spectroscopy. In the solid state, the cobalt atom displays a typical tetrahedral geometry and [...] Read more.

Dichloro-bis(1-cinnamyl-benzimidazole)-cobalt(II) was prepared in one step using a cobalt precursor CoCl₂ and corresponding substituted benzimidazole. The complex was fully characterized using IR, elemental analysis, and mass- and NMR spectroscopy. In the solid state, the cobalt atom displays a typical tetrahedral geometry and is coordinated to two chlorine atoms and two benzimidazole moieties. Full article

(This article belongs to the Section Structure Determination)

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2 pages, 136 KiB

Open AccessEditorial

Molbank—Aims and Scope Update

by Nicholas E. Leadbeater

Molbank 2024, 2024(4), M1909; https://doi.org/10.3390/M1909 - 30 Oct 2024

Abstract

Molbank is a unique journal, bringing together one-compound-per-paper short notes on synthetic compounds and natural products [...] Full article

7 pages, 1064 KiB

Open AccessCommunication

A Novel Approach for the Synthesis of 3,3′-((4-Methoxyphenyl)methylene)bis(4-hydroxyfuran-2(5H)-one) Employing Natural Deep Eutectic Solvents and Microwave Irradiation

by Maria-Anna Karadendrou, Ioanna Kostopoulou, Afroditi Christodoulou, Andromachi Tzani and Anastasia Detsi

Molbank 2024, 2024(4), M1910; https://doi.org/10.3390/M1910 - 30 Oct 2024

Abstract

Tetronic acid, a five-membered heterocyclic moiety present in various natural products, has emerged as a significant building block for many pharmaceutically active compounds. In this study, a novel protocol for the synthesis of the bis-tetronic acid 3,3′-((4-methoxyphenyl)methylene)bis(4-hydroxyfuran-2(5H)-one) (3) via [...] Read more.

Tetronic acid, a five-membered heterocyclic moiety present in various natural products, has emerged as a significant building block for many pharmaceutically active compounds. In this study, a novel protocol for the synthesis of the bis-tetronic acid 3,3′-((4-methoxyphenyl)methylene)bis(4-hydroxyfuran-2(5H)-one) (3) via a domino Knoevenagel–Michael reaction is presented. The natural deep eutectic solvent L-proline/glycerol 1:2 molar ratio was utilized as a solvent and catalyst, while the reaction was further promoted via microwave irradiation, providing the desired product in high yield (83%). The solvent was successfully recycled and reused up to three times. Full article

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