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Volume 2024
Issue 2
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Molbank, Volume 2024, Issue 2 (June 2024) – 19 articles

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6 pages, 1019 KiB  
Communication
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 (registering DOI) - 24 Apr 2024
Viewed by 150
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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Scheme 1

6 pages, 1469 KiB  
Short 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 (registering DOI) - 24 Apr 2024
Viewed by 165
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  
Short 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 172
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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Figure 1

8 pages, 1315 KiB  
Short 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 192
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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Figure 1

5 pages, 552 KiB  
Short 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 222
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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Scheme 1

5 pages, 640 KiB  
Short 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 (registering DOI) - 19 Apr 2024
Viewed by 231
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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Scheme 1

4 pages, 656 KiB  
Short 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 253
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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Figure 1

7 pages, 1059 KiB  
Short 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 275
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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Figure 1

6 pages, 1274 KiB  
Short 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 297
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  
Communication
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
Viewed by 298
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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Figure 1

7 pages, 4214 KiB  
Communication
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 433
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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Figure 1

6 pages, 382 KiB  
Short 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 - 09 Apr 2024
Viewed by 317
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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Scheme 1

6 pages, 2425 KiB  
Short 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 - 07 Apr 2024
Viewed by 431
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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Figure 1

5 pages, 620 KiB  
Short 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 - 01 Apr 2024
Viewed by 1068
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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Figure 1

6 pages, 1182 KiB  
Short 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 - 01 Apr 2024
Viewed by 421
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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Graphical abstract

9 pages, 1518 KiB  
Short 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 - 01 Apr 2024
Viewed by 444
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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5 pages, 809 KiB  
Short Note
(1RS,3SR)-1-(4-Methylbenzyl)-7-phenyl-5-oxa-6-azaspiro[2.4]hept-6-en-4-one
by Gleb D. Titov and Nikolai V. Rostovskii
Molbank 2024, 2024(2), M1799; https://doi.org/10.3390/M1799 - 01 Apr 2024
Viewed by 459
Abstract
The previously unknown cyclopropane spiro-fused with isoxazol-5-one ((1RS,3SR)-1-(4-methylbenzyl)-7-phenyl-5-oxa-6-azaspiro[2.4]hept-6-en-4-one) was synthesized from benzylideneisoxazol-5-one in 34% yield via double methylene transfer from diazomethane. The structure of the compound was established based on 1H, 13C, and 2D NMR spectroscopy and [...] Read more.
The previously unknown cyclopropane spiro-fused with isoxazol-5-one ((1RS,3SR)-1-(4-methylbenzyl)-7-phenyl-5-oxa-6-azaspiro[2.4]hept-6-en-4-one) was synthesized from benzylideneisoxazol-5-one in 34% yield via double methylene transfer from diazomethane. The structure of the compound was established based on 1H, 13C, and 2D NMR spectroscopy and high-resolution mass spectrometry, and confirmed by X-ray diffraction analysis. Full article
(This article belongs to the Section Organic Synthesis)
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Figure 1

7 pages, 1236 KiB  
Short Note
(E)-1-(4-Methoxyphenyl)-5-methyl-4-(1-phenyl-4-((2-(2,4,6-trichlorophenyl)hydrazineylidene)methyl)-1H-pyrazol-3-yl)-1H-1,2,3-triazole
by Bakr F. Abdel-Wahab, Hanan A. Mohamed, Benson M. Kariuki and Gamal A. El-Hiti
Molbank 2024, 2024(2), M1798; https://doi.org/10.3390/M1798 - 28 Mar 2024
Viewed by 510
Abstract
The reaction of equimolar quantities of 3-(1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde and (2,4,6-trichlorophenyl)hydrazine in ethanol containing concentrated hydrochloric acid (0.2 mL; 37%) as a catalyst under reflux for 2 h yielded 1-(1-(benzofuran-2-yl)ethylidene)-2-(2,4,6-trichlorophenyl)hydrazine. The crude produced was purified by crystallization using dimethylformamide to provide [...] Read more.
The reaction of equimolar quantities of 3-(1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde and (2,4,6-trichlorophenyl)hydrazine in ethanol containing concentrated hydrochloric acid (0.2 mL; 37%) as a catalyst under reflux for 2 h yielded 1-(1-(benzofuran-2-yl)ethylidene)-2-(2,4,6-trichlorophenyl)hydrazine. The crude produced was purified by crystallization using dimethylformamide to provide the title heterocycle in a 95% yield. The structure of the newly synthesized heterocycle was confirmed through X-ray diffraction and spectral analyses. Full article
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Figure 1

9 pages, 1429 KiB  
Communication
Aza-Diphosphido-Bridged Di-Iron Complexes Related to the [FeFe]-Hydrogenases
by Pankaj Das, Catherine Elleouet, François Y. Pétillon and Philippe Schollhammer
Molbank 2024, 2024(2), M1797; https://doi.org/10.3390/M1797 - 25 Mar 2024
Viewed by 604
Abstract
The reaction of the dianionic species [Fe2(CO)6(μ-PPh)2]2− with tBuN(CH2Cl)2 gives the di-iron carbonyl aza-diphosphido-bridged complex [Fe2(CO)6(µ-{P(Ph)CH2}2NtBu)] (1 [...] Read more.
The reaction of the dianionic species [Fe2(CO)6(μ-PPh)2]2− with tBuN(CH2Cl)2 gives the di-iron carbonyl aza-diphosphido-bridged complex [Fe2(CO)6(µ-{P(Ph)CH2}2NtBu)] (1). Attempts to prepare 1 by click-chemistry by reacting [Fe2(CO)6(μ-PHPh)2] with CH2O and tBuNH2 afforded a bis-phosphido compound [Fe2(CO)6(µ-P(Ph)CH2NHtBu)2] (2) which exists as two, syn and anti, isolable isomers depending on the relative orientation of the groups carried by the phosphorus atoms. In the presence of HBF4.Et2O, in dichloromethane, 1 leads to the stabilized ammonium species [Fe2(CO)6(µ-{P(Ph)CH2}2NHtBu)](BF4) (3). The derivatives 1–3 were characterized by IR and 1H, 31P-{1H} NMR spectroscopies. Their structures in a solid state were determined by X-ray diffraction analyses, which accord with their spectroscopic characteristics. Full article
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