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Molbank
Volume 2024
Issue 3
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Molbank, Volume 2024, Issue 3 (September 2024) – 46 articles

Cover Story (view full-size image): N,N'-bis(pyridin-3-ylmethyl)oxalamide (L) was characterized in several coordination compounds (CPs) with a variety of transition metal ions. Crystals of novel compound 1 were grown by slow evaporation of an MeCN/H2O mixture of L and Cd(NO3)2·4H2O. Single crystal X-ray diffraction analysis established 1 as [Cd(L)2(OH2)2](NO3)2·4H2O, consisting of a CP featuring cationic 1D-ribbons counterbalanced by nitrate anions. Each CdII node shows a pseudo-octahedral coordination by four pyridine N-atoms and two trans-disposed water molecules. The crystal packing results from the cooperation of π-π stacking and hydrogen bond. Compound 1 confirms the potential of dipicolyloxalmides as flexible ligands for a variety of CPs and opens new perspectives in the field of the crystal engineering of CPs and metal–organic frameworks. View this paper
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6 pages, 1319 KiB  
Short Note
2-Methylpropan-2-ammonium [(3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-[(2S)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-heptanoate
by Ioana-Georgeta Grosu, Alexandru Turza, Xenia Filip and Maria-Olimpia Miclaus
Molbank 2024, 2024(3), M1885; https://doi.org/10.3390/M1885 - 24 Sep 2024
Viewed by 666
Abstract
Pravastatin is a popular statin agent with applications in the treatment of cardiovascular diseases for patients with an abnormal lipid panel. The starting form of pravastatin is amorphous and following recrystallization, it becomes a crystalline solid with tert-butylamine salt molecules embedded within the [...] Read more.
Pravastatin is a popular statin agent with applications in the treatment of cardiovascular diseases for patients with an abnormal lipid panel. The starting form of pravastatin is amorphous and following recrystallization, it becomes a crystalline solid with tert-butylamine salt molecules embedded within the lattice. Its molecular and crystal structure were elucidated based on single-crystal X-ray diffraction and characterized by ss-NMR. Full article
(This article belongs to the Section Structure Determination)
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Figure 1

8 pages, 981 KiB  
Short Note
4-(10-Phenyl-9-Anthracenyl)-1,2-Benzenediol
by Nicola Edwards and Kelsey Harris
Molbank 2024, 2024(3), M1884; https://doi.org/10.3390/M1884 - 23 Sep 2024
Viewed by 903
Abstract
The title compound, 4-(10-phenyl-9-anthracenyl)-1,2-benzenediol, was synthesized using a two-step protocol. In the first step, 9-phenyl,10-bromoanthracene was coupled to 3,4-dimethoyphenylboronic acid by employing Pd(PPh3)4 as the catalyst and potassium carbonate as the base. Methoxy group removal was effected using HBr in [...] Read more.
The title compound, 4-(10-phenyl-9-anthracenyl)-1,2-benzenediol, was synthesized using a two-step protocol. In the first step, 9-phenyl,10-bromoanthracene was coupled to 3,4-dimethoyphenylboronic acid by employing Pd(PPh3)4 as the catalyst and potassium carbonate as the base. Methoxy group removal was effected using HBr in the presence of acetic acid in the second step. Overall, two novel 9,10-diphenylanthracence-based compounds were synthesized in this work; standard spectroscopic techniques and high-resolution mass spectrometry were employed in their characterization. The photophysical properties of these compounds are also reported. These compounds are potentially useful as sensors, catalysts and building blocks for larger architectures. Full article
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Figure 1

6 pages, 1036 KiB  
Communication
Thiazolylketol Acetates as Glycosyl Donors: Stereoselective Synthesis of a C-Ketoside
by Clark Ferrari, Alessandro Dondoni and Alberto Marra
Molbank 2024, 2024(3), M1883; https://doi.org/10.3390/M1883 - 23 Sep 2024
Cited by 1 | Viewed by 800
Abstract
We have already proven that thiazolylketol acetates, synthetised by addition of 2-lithiothiazole to sugar lactones followed by acetylation, are efficient glycosyl donors in the presence of O-, N-, and P-nucleophiles. We describe here their first use in the C-glycosidation using [...] Read more.
We have already proven that thiazolylketol acetates, synthetised by addition of 2-lithiothiazole to sugar lactones followed by acetylation, are efficient glycosyl donors in the presence of O-, N-, and P-nucleophiles. We describe here their first use in the C-glycosidation using trimetylsilyl cyanide as the acceptor in order to prepare, after thiazole-to-formyl unmasking and reduction, the corresponding C-ketosides. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Graphical abstract

7 pages, 243 KiB  
Communication
The Effects of Ceric Ammonium Nitrate in the Oxidation of 2-Benzyl-1,4-dimethoxybenzene Derivatives
by Marcello Casertano, Anna Aiello, Marialuisa Menna and Concetta Imperatore
Molbank 2024, 2024(3), M1882; https://doi.org/10.3390/M1882 - 16 Sep 2024
Viewed by 872
Abstract
The one- or two-electron reduction in quinone compounds gives rise to semiquinones and hydroquinones, respectively, which, in turn, can be oxidized back to quinones, generating a cyclic redox system with the production of reactive oxygen species (ROS). For these reasons, quinone derivatives participate [...] Read more.
The one- or two-electron reduction in quinone compounds gives rise to semiquinones and hydroquinones, respectively, which, in turn, can be oxidized back to quinones, generating a cyclic redox system with the production of reactive oxygen species (ROS). For these reasons, quinone derivatives participate in various biological processes in metabolic pathways, such as oxidative reactions and electron transport. In addition, natural quinone compounds as well as their semisynthetic and/or synthetically produced derivatives are of great pharmacological interest for the discovery and design of new drugs. As a result, their chemical reactivity as well as new methods for their synthesis are being investigated on an ongoing basis. Herein, a mild and efficient synthesis to obtain 2-(4-benzyl substituted)-1,4-dimethoxybenzene derivatives is reported. In addition, an evaluation of the effects on the quinone/diquinone ratio in the reaction product in relation to different ways of adding the oxidant CAN to the arene solution is discussed. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Scheme 1

4 pages, 586 KiB  
Short Note
rel-(2R,3S)-2-((Diphenylmethylene)amino)-5-oxo-5-phenyl-3-(thiophen-2-yl)pentanenitrile
by Donka N. Tasheva and Vesela M. Mihaylova
Molbank 2024, 2024(3), M1881; https://doi.org/10.3390/M1881 - 11 Sep 2024
Viewed by 823
Abstract
The reaction of 2-((diphenylmethylene)amino)acetonitrile with (E)-1-phenyl-3-(thiophen-2-yl)prop-2-en-1-one was performed by using 33% NaOH in CH3CN for 30 min at 0 °C. The main product—rel-(2R,3S)-2-((diphenylmethylene)amino)-5-oxo-5-phenyl-3-(thiophen-2-yl)pentanenitrile—was isolated and characterized by IR, 1H NMR, 13C NMR, 1H-1H COSY, and high-resolution mass spectrometry (HRMS). Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Graphical abstract

7 pages, 3596 KiB  
Communication
The Crystal Structures of Some Bromo-Derivatives of the DPPH Stable Free Radical
by Adela F. Dobre, Augustin M. Madalan and Petre Ionita
Molbank 2024, 2024(3), M1880; https://doi.org/10.3390/M1880 - 10 Sep 2024
Viewed by 674
Abstract
Bromination of the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical with bromine or N-bromo-succinimide (NBS) affords a complex mixture of bromo- and nitro-derivatives of the starting material. In this study, by chromatographic separation, most of the reaction products were isolated. Suitable crystals for X-ray measurements [...] Read more.
Bromination of the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical with bromine or N-bromo-succinimide (NBS) affords a complex mixture of bromo- and nitro-derivatives of the starting material. In this study, by chromatographic separation, most of the reaction products were isolated. Suitable crystals for X-ray measurements were obtained and characterized for the compounds 2-p-bromophenyl-2-phenyl-1-picrylhydrazyl free radical (Br-DPPH), 2-p-bromophenyl-2-phenyl-1-picrylhydrazine (Br-DPPH-H), and 2,2-(p-bromophenyl)-1-(2-bromo-4,6-dinitrophenyl)hydrazine (Br2-DPPBr-H). Full article
(This article belongs to the Section Structure Determination)
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Figure 1

5 pages, 778 KiB  
Communication
Synthesis of Novel Sulfonamide Derivatives Featuring 1-(Methylsulfonyl)-4-(2,3,4-Trimethoxybenzyl)Piperazine Core Structures
by Iliyan Ivanov, Stanimir Manolov, Dimitar Bojilov, Diyana Dimitrova and Paraskev Nedialkov
Molbank 2024, 2024(3), M1879; https://doi.org/10.3390/M1879 - 9 Sep 2024
Viewed by 1139
Abstract
Herein we report the synthesis of three novel sulfonamide derivatives of trimetazidine—medication primarily used to treat angina pectoris. The new compounds have been fully characterized with their melting point, 1H- and 13C-NMR, UV, and mass spectrometry. The collected data confirm the [...] Read more.
Herein we report the synthesis of three novel sulfonamide derivatives of trimetazidine—medication primarily used to treat angina pectoris. The new compounds have been fully characterized with their melting point, 1H- and 13C-NMR, UV, and mass spectrometry. The collected data confirm the successful synthesis and structural integrity of the new molecules. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Figure 1

6 pages, 1565 KiB  
Communication
2,3-Dihydrobenzo[e][1,3]oxazin-4-one
by R. Alan Aitken, David B. Cordes, Mhairi R. Kinahan and Aidan P. McKay
Molbank 2024, 2024(3), M1878; https://doi.org/10.3390/M1878 - 5 Sep 2024
Viewed by 781
Abstract
The title compound and its hydroxymethyl precursor have been fully characterised for the first time. The IR spectra, fully assigned 1H and 13C NMR spectra, and X-ray structures are presented for both compounds. Both compounds form hydrogen-bonded dimers in the crystal structures. Full article
(This article belongs to the Section Structure Determination)
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Graphical abstract

6 pages, 1741 KiB  
Communication
Attempted Synthesis of the Pseudomonas aeruginosa Metabolite 2-Benzyl-4(1H)-quinolone and Formation of 3-Methylamino-2-(2-nitrobenzoyl)-4H-naphthalen-1-one as an Unexpected Product
by Plamen Angelov, Yordanka Mollova-Sapundzhieva and Paraskev Nedialkov
Molbank 2024, 2024(3), M1877; https://doi.org/10.3390/M1877 - 29 Aug 2024
Viewed by 674
Abstract
The unusual reactivity of key enamine intermediates led to the formation of 3-methylamino-2-(2-nitrobenzoyl)-4H-naphthalen-1-one as an unexpected product in an attempted synthesis of the P. aeruginosa metabolite 2-benzyl-4(1H)-quinolone. Although the synthesis of the natural product has not been successful, this [...] Read more.
The unusual reactivity of key enamine intermediates led to the formation of 3-methylamino-2-(2-nitrobenzoyl)-4H-naphthalen-1-one as an unexpected product in an attempted synthesis of the P. aeruginosa metabolite 2-benzyl-4(1H)-quinolone. Although the synthesis of the natural product has not been successful, this methodology allows for the easy preparation of novel derivatives carrying a carboxamide moiety at the C3 position. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Figure 1

8 pages, 1286 KiB  
Communication
Synthesis of Diastereomeric 2,6-bis{[3-(2-Hydroxy-5-substitutedbenzyl)octahydro-1H-benzimidazol-1-yl]methyl}-4-substituted Phenols (R = Me, OMe) by Mannich-Type Tandem Reactions
by Diego Quiroga, Jaime Ríos-Motta and Augusto Rivera
Molbank 2024, 2024(3), M1876; https://doi.org/10.3390/M1876 - 28 Aug 2024
Viewed by 826
Abstract
The synthesis and characterization of two novel diastereomeric Mannich bases was carried out from the reaction of the cyclic aminal (2R,7R,11S,16S)-1,8,10,17-tetraazapentacyclo[8.8.1.1.8,170.2,70.11,16]icosane 1 and p-cresol 2a and 4-methoxyphenol 2b [...] Read more.
The synthesis and characterization of two novel diastereomeric Mannich bases was carried out from the reaction of the cyclic aminal (2R,7R,11S,16S)-1,8,10,17-tetraazapentacyclo[8.8.1.1.8,170.2,70.11,16]icosane 1 and p-cresol 2a and 4-methoxyphenol 2b in a water/dioxane mixture. The title compounds (4a–b) are interesting because bearing two 3-(2-hydroxy-5-substitutedbenzyl)octahydro-1H-benzimidazol-1-yl]methyl} substituents joined to an arenol ring. The formation of these new Mannich bases in the reaction mixture can be explained by aminomethylation of previously reported di-Mannich base 2,2′-((hexahydro-1H-benzo[d]imidazole-1,3(2H)-diyl)bis(methylene))bis(4-substituentphenol) 3a–b. NMR analysis demonstrated that compounds 4a–b were formed as diastereomeric mixtures. Subsequent experiments revealed that at longer reaction times, the percentage yield of these new products increased considerably (yield percentages up to 22–27%), suggesting a nucleophilic competition between the p-substituted phenols and Mannich bases of type 3 for aminal 1. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Graphical abstract

5 pages, 870 KiB  
Short Note
(R/S)-Ethyl 2-Acetoxy-4-phenyl-4H-chromene-3-carboxylate
by Nevena I. Petkova-Yankova, Ana I. Koleva and Rositca D. Nikolova
Molbank 2024, 2024(3), M1875; https://doi.org/10.3390/M1875 - 26 Aug 2024
Viewed by 890
Abstract
A simple protocol for the preparation of O-acylated enol form (R/S)-ethyl-2-acetoxy-4-phenyl-4H-chromene-3-carboxylate 5 was presented. The compound was characterized by 1H-, 13C-and DEPT135 NMR spectra, including {1H,1H} COSY, {1H,13C} HSQC, {1 [...] Read more.
A simple protocol for the preparation of O-acylated enol form (R/S)-ethyl-2-acetoxy-4-phenyl-4H-chromene-3-carboxylate 5 was presented. The compound was characterized by 1H-, 13C-and DEPT135 NMR spectra, including {1H,1H} COSY, {1H,13C} HSQC, {1H,13C} HMBC, and 2D-NOESY spectra. The preferred regioselectivity for O-acylation of 3,4-dihydrocoumarin 5 in the presence of substituent in the 4th position in the chroman ring and accounting for the steric hindrance of the ester group in the 3rd place was confirmed. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Figure 1

10 pages, 3300 KiB  
Short Note
8-(2-Methoxyphenyl)-6-methyl-2-(1-methyl-1H-benzo[d]imidazol-2-yl)quinoline
by Maria Ivanova, Joana Zaharieva, Martin Tsvetkov, Vesela Lozanova, Bernd Morgenstern and Rumen Lyapchev
Molbank 2024, 2024(3), M1874; https://doi.org/10.3390/M1874 - 21 Aug 2024
Viewed by 757
Abstract
For very first time, we report the synthesis of 8-(2-methoxyphenyl)-6-methyl-2-(1-methyl-1H-benzo[d]imidazol-2-yl)quinoline 1. This was achieved in several steps, including usage of the Suzuki reaction for functionalization of 2-(1H-benzo[d]imidazol-2-yl)quinoline moiety. The new compound exhibits blue fluorescence. Its structure was confirmed [...] Read more.
For very first time, we report the synthesis of 8-(2-methoxyphenyl)-6-methyl-2-(1-methyl-1H-benzo[d]imidazol-2-yl)quinoline 1. This was achieved in several steps, including usage of the Suzuki reaction for functionalization of 2-(1H-benzo[d]imidazol-2-yl)quinoline moiety. The new compound exhibits blue fluorescence. Its structure was confirmed with 1D and 2D NMR spectroscopy, IR spectroscopy, high-resolution mass spectrometry and X-ray analysis. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Figure 1

4 pages, 553 KiB  
Short Note
3-Ethoxycarbonyl-1,4-benzodioxin-2-carboxylic Acid
by Edoardo Armano, Alessandro Giraudo, Camillo Morano, Marco Pallavicini and Cristiano Bolchi
Molbank 2024, 2024(3), M1873; https://doi.org/10.3390/M1873 - 19 Aug 2024
Viewed by 869
Abstract
3-Ethoxycarbonyl-1,4-benzodioxin-2-carboxylic acid, a novel 2,3-disubstituted benzodioxin, was prepared from readily available 1,4-benzodioxin-2-carboxylic acid by lithiation at C(3) and a reaction with the electrophile ethyl chloroformate. The analytical characterization of the product was performed via IR, 1H-NMR, 13C-NMR, HRMS, and HPLC-UV. Due [...] Read more.
3-Ethoxycarbonyl-1,4-benzodioxin-2-carboxylic acid, a novel 2,3-disubstituted benzodioxin, was prepared from readily available 1,4-benzodioxin-2-carboxylic acid by lithiation at C(3) and a reaction with the electrophile ethyl chloroformate. The analytical characterization of the product was performed via IR, 1H-NMR, 13C-NMR, HRMS, and HPLC-UV. Due to the unsymmetrically disubstituted unsaturation, the obtained monoester of 1,4-benzodioxin-2,3-dicarboxylic acid is a building block of great potential in the synthesis of a variety of compounds containing the benzodioxin or benzodioxane scaffold. Full article
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Figure 1

9 pages, 433 KiB  
Communication
Synthesis and Antimicrobial Evaluation of 2-[2-(9H-Fluoren-9-ylidene)hydrazin-1-yl]-1,3-thiazole Derivatives
by Kazimieras Anusevičius, Ignė Stebrytė and Povilas Kavaliauskas
Molbank 2024, 2024(3), M1872; https://doi.org/10.3390/M1872 - 19 Aug 2024
Viewed by 867
Abstract
Fluorenyl-hydrazonothiazole derivatives 2–7 were synthesized by the Hantzsch reaction from 2-(9H-fluoren-9-ylidene)hydrazine-1-carbothioamide (1) and the corresponding α-halocarbonyl compounds in THF or 1,4-dioxane solvent. A base catalyst is not necessary for synthesising thiazoles, but it can shorten the reaction time. The [...] Read more.
Fluorenyl-hydrazonothiazole derivatives 2–7 were synthesized by the Hantzsch reaction from 2-(9H-fluoren-9-ylidene)hydrazine-1-carbothioamide (1) and the corresponding α-halocarbonyl compounds in THF or 1,4-dioxane solvent. A base catalyst is not necessary for synthesising thiazoles, but it can shorten the reaction time. The antimicrobial properties of all synthesized compounds were screened for multidrug-resistant microorganism strains. The minimum inhibitory concentration of the tested compounds against Gram-positive bacteria and fungi was higher than 256 μg/mL, but several compounds had activity against Gram-positive strains. Full article
(This article belongs to the Collection Heterocycle Reactions)
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Graphical abstract

4 pages, 1012 KiB  
Short Note
1-(Dicyanomethylene)-3-hydroxy-1H-indene-2-carboxylic Acid
by Sofia D. Usova, Ekaterina A. Knyazeva and Oleg A. Rakitin
Molbank 2024, 2024(3), M1871; https://doi.org/10.3390/M1871 - 19 Aug 2024
Viewed by 893
Abstract
Bulk heterojunction solar cells are among the most promising organic solar cells (OSCs). One of the two important parts of OSCs are acceptors, and the development of the design and synthesis of non-fullerene acceptors involves an electron-deficient heterocyclic central core and anchor acceptor [...] Read more.
Bulk heterojunction solar cells are among the most promising organic solar cells (OSCs). One of the two important parts of OSCs are acceptors, and the development of the design and synthesis of non-fullerene acceptors involves an electron-deficient heterocyclic central core and anchor acceptor malonitrile derivatives of 3-methylene-2,3-dihydro-1H-inden-1-ones. In this communication, an intermediate for the synthesis of this compound, 1-(dicyanomethylene)-3-hydroxy-1H-indene-2-carboxylic acid, was prepared by the Perkin reaction of 2-(3-oxoisobenzofuran-1(3H)-ylidene)malononitrile with tert-butyl acetoacetate in the presence of acetic anhydride and triethylamine. The structure of the newly synthesized compound was established by means of elemental analysis, high-resolution mass spectrometry, 1H NMR, 13C NMR and IR spectroscopy, and mass spectrometry. Full article
(This article belongs to the Collection Heterocycle Reactions)
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Scheme 1

6 pages, 1523 KiB  
Short Note
3-((λ3-Oxidanylidene)(propylamino)methyl)-2-ethoxybenzo[e]-[1,2]oxaphosphinine-2-oxide
by Ana I. Koleva, Nevena I. Petkova-Yankova and Rositca D. Nikolova
Molbank 2024, 2024(3), M1870; https://doi.org/10.3390/M1870 - 19 Aug 2024
Viewed by 803
Abstract
A method for the simple preparation of 2-ethoxy-N-propylbenzo[e][1,2]oxaphosphinine-3-carboxamide 2-oxide via an ultrasound technique using catalytic amounts of CuI is reported. The formation of the amide could indicate the isomerization of the formed E-alkene intermediate to its Z-form, assisted by the sonication [...] Read more.
A method for the simple preparation of 2-ethoxy-N-propylbenzo[e][1,2]oxaphosphinine-3-carboxamide 2-oxide via an ultrasound technique using catalytic amounts of CuI is reported. The formation of the amide could indicate the isomerization of the formed E-alkene intermediate to its Z-form, assisted by the sonication irradiation, and such transformation under the presented conditions has not been previously reported in the literature. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Scheme 1

8 pages, 494 KiB  
Short Note
8-Iodo-4-methyl-2-oxo-2H-chromen-7-yl Benzenesulfonate
by Luis Pulido-Moreno, Andrés Parra-Tibocha, Alexander Ladino-Bejarano, Mario A. Macías, Diana Becerra and Juan-Carlos Castillo
Molbank 2024, 2024(3), M1869; https://doi.org/10.3390/M1869 - 19 Aug 2024
Viewed by 1481
Abstract
We report a straightforward and efficient synthesis of 4-methyl-2-oxo-2H-chromen-7-yl benzenesulfonate (3a) and 8-iodo-4-methyl-2-oxo-2H-chromen-7-yl benzenesulfonate (3b) in good yields through an O-sulfonylation reaction of 7-hydroxy-2H-chromen-2-ones 1a and 1b with benzenesulfonyl chloride 2 mediated [...] Read more.
We report a straightforward and efficient synthesis of 4-methyl-2-oxo-2H-chromen-7-yl benzenesulfonate (3a) and 8-iodo-4-methyl-2-oxo-2H-chromen-7-yl benzenesulfonate (3b) in good yields through an O-sulfonylation reaction of 7-hydroxy-2H-chromen-2-ones 1a and 1b with benzenesulfonyl chloride 2 mediated by triethylamine in dichloromethane at ambient temperature. The aryl sulfonyl esters were characterized using spectroscopic, spectrometric, and thermal analyses. Full article
(This article belongs to the Collection Heterocycle Reactions)
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Scheme 1

8 pages, 1461 KiB  
Short Note
2-(2,6-Diisopropylphenyl)-1-methylimidazo[1,5-a]quinolin-2-ium Tetrafluoroborate
by Lyuben Borislavov, Iskra Z. Koleva, Vesela Lozanova, Maria Ivanova and Rumen Lyapchev
Molbank 2024, 2024(3), M1868; https://doi.org/10.3390/M1868 - 15 Aug 2024
Viewed by 682
Abstract
A new heterocyclic compound, 2-(2,6-diisopropylphenyl)-1-methylimidazo[1,5-a]quinolin-2-ium tetrafluoroborate 1 was obtained from its precursor, N-(2,6-diisopropylphenyl)-N-(quinolin-2-ylmethyl)acetamide 2, by POCl3-mediated cyclization. For the first time, tertiary acetamide 2, the precursor of 1, was synthesized by using commercially [...] Read more.
A new heterocyclic compound, 2-(2,6-diisopropylphenyl)-1-methylimidazo[1,5-a]quinolin-2-ium tetrafluoroborate 1 was obtained from its precursor, N-(2,6-diisopropylphenyl)-N-(quinolin-2-ylmethyl)acetamide 2, by POCl3-mediated cyclization. For the first time, tertiary acetamide 2, the precursor of 1, was synthesized by using commercially available starting materials. The structure of 1 was unquestionably confirmed by 1H, 13C, 2D-NMR, and IR spectroscopies and mass spectrometry. Its optical properties were also studied. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Figure 1

7 pages, 1581 KiB  
Short Note
Bis(3-(((4-methoxybenzyl)oxy)methyl)-5,6-dihydro-1,4-dithiin-2-yl)methanol
by Anna Esposito and Annalisa Guaragna
Molbank 2024, 2024(3), M1867; https://doi.org/10.3390/M1867 - 14 Aug 2024
Viewed by 817
Abstract
An organolithium reagent containing a 5,6-dihydro-1,4-dithiin moiety has been herein used as homologating agent to build up a fully protected divinylcarbinol by two different synthetic procedures, respectively, based on a step-by-step approach or a tandem process. The resulting molecule contains two double bonds [...] Read more.
An organolithium reagent containing a 5,6-dihydro-1,4-dithiin moiety has been herein used as homologating agent to build up a fully protected divinylcarbinol by two different synthetic procedures, respectively, based on a step-by-step approach or a tandem process. The resulting molecule contains two double bonds masked by two dithiodimethylene bridges that can be stereoselectively removed to give a E,E- or Z,Z-configured divinylcarbinol. These products could then be conveniently functionalized, for example, with hydroxyl or amino functions, for the construction of the skeleton of more complex systems. Full article
(This article belongs to the Collection Molecules from Side Reactions)
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Figure 1

4 pages, 347 KiB  
Short Note
(E)-5-(3-Oxo-3-(3,4,5-trimethoxyphenyl)prop-1-en-1-yl)benzo[d]oxazol-2(3H)-one
by Yordanka B. Ivanova, Filip E. Svetoslavov and Ognyan I. Petrov
Molbank 2024, 2024(3), M1866; https://doi.org/10.3390/M1866 - 13 Aug 2024
Viewed by 763
Abstract
The title compound, (E)-5-(3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-en-1-yl)benzo[d]oxazol-2(3H)-one, was synthesized by the acid- and base-catalyzed aldol condensation of 2-oxo-2,3-dihydrobenzo[d]oxazole-5-carbaldehyde and 3,4,5-trimethoxyacetophenone. The structure of the target compound was confirmed using 1H NMR, 13C NMR, HRMS, and elemental analysis. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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8 pages, 386 KiB  
Communication
Synthesis of Tetrahydroberberine N,N-Derived O-Acetamides
by Ivan Vasil’evich Nechepurenko, Nina Ivanovna Komarova and Nariman Faridovich Salakhutdinov
Molbank 2024, 2024(3), M1865; https://doi.org/10.3390/M1865 - 13 Aug 2024
Viewed by 891
Abstract
The reaction of berberine derivatives containing at the O-9 position N,N-disubstituted acetamide fragments with sodium borohydride in methanol at 0 °C leads to a mild reduction of the “C” cycle with the formation of corresponding tetrahydroberberine derivatives with moderate to good yields. Full article
(This article belongs to the Section Natural Product Chemistry)
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Graphical abstract

5 pages, 390 KiB  
Short Note
5′-Oxospiro-(fluorene-9,4′-imidazolidine)-2′-thione
by Dimitar Stoitsov, Marin Marinov, Plamen Penchev, Petya Marinova and Neyko Stoyanov
Molbank 2024, 2024(3), M1864; https://doi.org/10.3390/M1864 - 8 Aug 2024
Viewed by 723
Abstract
The structure verification of 5′-oxospiro-(fluorene-9,4′-imidazolidine)-2′-thione by NMR is reported. Toward this aim, 2D NMR techniques including 1H-1H COSY, HMQC, and HMBC experiments were used to assist with the assignment of the 1H and 13C chemical shifts for the [...] Read more.
The structure verification of 5′-oxospiro-(fluorene-9,4′-imidazolidine)-2′-thione by NMR is reported. Toward this aim, 2D NMR techniques including 1H-1H COSY, HMQC, and HMBC experiments were used to assist with the assignment of the 1H and 13C chemical shifts for the corresponding structure. The mutual interpretation of the 1D and 2D NMR spectra ensured a complete and accurate 1H and 13C NMR data assignment for 5′-oxospiro-(fluorene-9,4′-imidazolidine)-2′-thione. Full article
(This article belongs to the Section Structure Determination)
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5 pages, 950 KiB  
Short Note
3-((2-(4-Chloro-5-ethoxy-2-nitrophenoxy)acetamido)methyl)phenyl-dimethylcarbamate
by Rosalba Leuci, Daniela Dininno, Marco Paparella and Luca Piemontese
Molbank 2024, 2024(3), M1863; https://doi.org/10.3390/M1863 - 5 Aug 2024
Viewed by 884
Abstract
In this study, we report the synthesis of 3-((2-(4-chloro-5-ethoxy-2-nitrophenoxy)acetamido)methyl)phenyl-dimethylcarbamate, designed on the basis of the structures of the commercial acetylcholinesterase inhibitor drug rivastigmine and a substituted aryloxyacetic acid, aiming at a multi-target approach to the therapy of Alzheimer’s disease. The hybrid was obtained [...] Read more.
In this study, we report the synthesis of 3-((2-(4-chloro-5-ethoxy-2-nitrophenoxy)acetamido)methyl)phenyl-dimethylcarbamate, designed on the basis of the structures of the commercial acetylcholinesterase inhibitor drug rivastigmine and a substituted aryloxyacetic acid, aiming at a multi-target approach to the therapy of Alzheimer’s disease. The hybrid was obtained thanks to a synthesized intermediate by-product. The compound was fully characterized by using 1H and 13C NMR, FT-IR and HRMS. Full article
(This article belongs to the Collection Molecules from Side Reactions)
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6 pages, 4050 KiB  
Short Note
(E)-1-(2,5-Dimethylphenyl)-3-phenylprop-2-en-1-one
by David B. Cordes, Iain A. Smellie and Brian A. Chalmers
Molbank 2024, 2024(3), M1862; https://doi.org/10.3390/M1862 - 1 Aug 2024
Viewed by 969
Abstract
X-ray crystallography has been used to characterize the title compound for the first time; 1H NMR, 13C NMR and IR spectroscopic data have also been updated from earlier reports. We also report the melting point of the title compound. Full article
(This article belongs to the Section Structure Determination)
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Graphical abstract

7 pages, 1776 KiB  
Short Note
Catena-[Triaquabis(μ2-1,4-bis(diphenylphosphoryl)butane)nitrato-κ2O-praseodymium(III)] Nitrate Monohydrate Methanol Solvate
by Eilidh S. M. Fern, Maia I. Lunt, Guy D. Minch, Julia Roeterdink, Ana P. Scheu Rodriguez, Charlotte A. Smith, Johnathan J. Venters, Aidan P. McKay, David B. Cordes and Brian A. Chalmers
Molbank 2024, 2024(3), M1861; https://doi.org/10.3390/M1861 - 31 Jul 2024
Viewed by 862
Abstract
The bidentate ligand, 1,4-bis(diphenlyphosphoryl)butane (dppbO2), was used to prepare a 1D polymeric Pr(III) complex which was characterised by single-crystal X-ray diffraction. Full article
(This article belongs to the Section Structure Determination)
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5 pages, 1506 KiB  
Short Note
(E)-1-(2,4-Dinitrophenyl)-2-(2-((1R,3R,5S,Z)-2-ethylidene-6,6-dimethylbicyclo[3.1.1]heptan-3-yl)ethylidene)hydrazine
by Zhengjie He, Sergey Lindeman and William A. Donaldson
Molbank 2024, 2024(3), M1860; https://doi.org/10.3390/M1860 - 30 Jul 2024
Viewed by 693
Abstract
The hydrovinylation of nopadiene gave a single 1,4-addition product (1) as an oil. A 3- step transformation of 3 gave 2,4-dinitrophenylhydrazone 6 as a crystalline compound. X-ray diffraction analysis of 6 confirmed the stereochemical assignments about the exocyclic olefin as well [...] Read more.
The hydrovinylation of nopadiene gave a single 1,4-addition product (1) as an oil. A 3- step transformation of 3 gave 2,4-dinitrophenylhydrazone 6 as a crystalline compound. X-ray diffraction analysis of 6 confirmed the stereochemical assignments about the exocyclic olefin as well as at stereocenter C(3). Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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6 pages, 915 KiB  
Short Note
3a-(4-Chlorophenyl)-1-thioxo-2,3,3a,4-tetrahydroimidazo[1,5-a]quinazolin-5(1H)-one
by Andrea Defant, Nicole Innocenti and Ines Mancini
Molbank 2024, 2024(3), M1859; https://doi.org/10.3390/M1859 - 28 Jul 2024
Viewed by 848
Abstract
With the aim of producing new heterocycle molecules, the previously reported 2-(aminomethyl)-2-(4-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one was converted efficiently by reacting with N,N′-dithiocarbonyldiimidazole (DTCI) to produce the substituted imidazolidine-2-thione moiety inserted in a three-fused-ring scaffold of the title compound. The molecular composition was confirmed [...] Read more.
With the aim of producing new heterocycle molecules, the previously reported 2-(aminomethyl)-2-(4-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one was converted efficiently by reacting with N,N′-dithiocarbonyldiimidazole (DTCI) to produce the substituted imidazolidine-2-thione moiety inserted in a three-fused-ring scaffold of the title compound. The molecular composition was confirmed by a high-resolution MS experiment, and its structure was elucidated by 1H, 13CNMR, and IR analyses. The thioacetamide form of the product was supported by density functional theory (DFT)–NMR analysis where 13C chemical shifts of the thioacetamide form and of its iminothiol tautomer were calculated in chloroform at the BP86/Jgauss-TZP2 level of theory. The very strong linear correlation between 13C chemical shifts from experimental findings and by calculation for the NHC=S form confirmed the structure. Full article
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11 pages, 4146 KiB  
Communication
Synthesis and Characterization of Novel Indazole–Sulfonamide Compounds with Potential MAPK1 Inhibitory Activity for Cancer Treatment
by Nassima Saghdani, Abdelali Chihab, Nabil El Brahmi and Saïd El Kazzouli
Molbank 2024, 2024(3), M1858; https://doi.org/10.3390/M1858 - 26 Jul 2024
Cited by 2 | Viewed by 1107
Abstract
Indazoles are a very important group of nitrogen-containing heterocycles with a wide range of biological and medicinal applications. These properties make them highly attractive for drug development, particularly when combined with sulfonamides to enhance their medicinal potential. In this work, we synthesized an [...] Read more.
Indazoles are a very important group of nitrogen-containing heterocycles with a wide range of biological and medicinal applications. These properties make them highly attractive for drug development, particularly when combined with sulfonamides to enhance their medicinal potential. In this work, we synthesized an indazole-based sulfonamide, namely the 1-((2-chloro-5-methoxyphenyl)sulfonyl)-5-nitro-1H-indazole (3). The reduction of the nitro group of 5-nitroindazole (1) to its corresponding amine was also performed to yield compound (4). Both compounds’ structures were elucidated using various spectroscopic techniques such as 1H NMR, 13C NMR, infrared (IR), and high-resolution mass spectrometry (HRMS). Our molecular docking studies suggest that compounds (3) and (4) have a strong affinity for MAPK1, indicating their potential as cancer treatments. Full article
(This article belongs to the Collection Heterocycle Reactions)
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9 pages, 3331 KiB  
Communication
Synthesis, Characterization, and Docking Study of a Novel Indole Derivative Containing a Tosyl Moiety as Anti-Oxidant Agent
by Abdelali Chihab, Nabil El Brahmi and Saïd El Kazzouli
Molbank 2024, 2024(3), M1857; https://doi.org/10.3390/M1857 - 26 Jul 2024
Cited by 1 | Viewed by 1056
Abstract
Indole derivatives are key components of natural products and possess a wide range of biological and pharmaceutical applications. Here, we present the synthesis of a new indole derivative, namely 2-(1-ethyl-5-nitro-1H-indole-7-carbonyl)butyl 4-methylbenzenesulfonate. The structural elucidation of this compound was accomplished through comprehensive [...] Read more.
Indole derivatives are key components of natural products and possess a wide range of biological and pharmaceutical applications. Here, we present the synthesis of a new indole derivative, namely 2-(1-ethyl-5-nitro-1H-indole-7-carbonyl)butyl 4-methylbenzenesulfonate. The structural elucidation of this compound was accomplished through comprehensive spectroscopic analysis, including Fourier-transform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR), and high-resolution mass spectrometry (HRMS). Our molecular docking study revealed that this compound exhibits strong affinity towards tyrosinase, making it a promising candidate as an antioxidant agent. Full article
(This article belongs to the Collection Heterocycle Reactions)
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4 pages, 303 KiB  
Short Note
N-(2-(Benzylamino)ethyl)-4-(naphthalene-1-sulfonamido)benzamide
by Rosalba Leuci, Fulvio Loiodice and Luca Piemontese
Molbank 2024, 2024(3), M1856; https://doi.org/10.3390/M1856 - 25 Jul 2024
Viewed by 786
Abstract
In this study, we report the synthesis of N-(2-(benzylamino)ethyl)-4-(naphthalene-1-sulfonamido)benzamide, designed on the basis of the structures of the PPARγ partial agonist SR2067 and of the commercial acetylcholinesterase inhibitor drug donepezil, aiming for a multi-target approach for the therapy of elderly diseases, such as [...] Read more.
In this study, we report the synthesis of N-(2-(benzylamino)ethyl)-4-(naphthalene-1-sulfonamido)benzamide, designed on the basis of the structures of the PPARγ partial agonist SR2067 and of the commercial acetylcholinesterase inhibitor drug donepezil, aiming for a multi-target approach for the therapy of elderly diseases, such as diabetes and Alzheimer’s disease. The compound was fully characterized by using 1H and 13C NMR, FT-IR and HRMS. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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