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Molbank
Volume 2023
Issue 3
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Molbank, Volume 2023, Issue 3 (September 2023) – 58 articles

Cover Story (view full-size image): Pterins consist of fused pyrazine and pyrimidine rings with –NH2 and =O functions on the latter. Their name comes from the Greek word pteron, meaning “wing”. They were first isolated as pierid butterflies’ wing pigments. Derivatives have also been found in the active sites of enzymes, further emphasizing their biological importance. In the course of bioinspired studies, a new alkyne-functionalized artificial pterin was synthesized by reacting 7-chloropterin with propargyl. The chemical structure of the compound was validated via NMR spectroscopy, Mass spectrometry, elemental analysis, and X-ray crystallography. The novel pterin derivative, in contrast to typical pterin behavior, was shown to be soluble or even well soluble in almost any solvent except water. This feature facilitates derivatization, as shown via the introduction of terminal chlorine. View this paper
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6 pages, 1664 KiB  
Short Note
2,2′-Trisulfanediyldibenzoyl Chloride
by R. Alan Aitken, Alexandra H. Campbell, Chloé E. Fletcher and Alexandra M. Z. Slawin
Molbank 2023, 2023(3), M1731; https://doi.org/10.3390/M1731 - 21 Sep 2023
Viewed by 1303
Abstract
The X-ray structure of the title compound, formed at low conversion in the reaction of thiosalicylic acid with thionyl chloride, has been determined. The acid chloride groups are oriented to permit an attractive non-bonding O…S interaction. Mechanisms are suggested for the formation of [...] Read more.
The X-ray structure of the title compound, formed at low conversion in the reaction of thiosalicylic acid with thionyl chloride, has been determined. The acid chloride groups are oriented to permit an attractive non-bonding O…S interaction. Mechanisms are suggested for the formation of this unexpected product. 1H and 13C NMR data are also reported for the first time for the major reaction product, 2-mercaptobenzoyl chloride. Full article
(This article belongs to the Section Structure Determination)
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Graphical abstract

4 pages, 827 KiB  
Short Note
4-(4-(2-Bromoethyl)phenoxy)-2,3,5,6-tetrafluoropyridine
by Tiffany H. Li, Lucas C. Messer, Nathan J. Weeks, Timothy J. Fuhrer and Scott T. Iacono
Molbank 2023, 2023(3), M1730; https://doi.org/10.3390/M1730 - 19 Sep 2023
Cited by 1 | Viewed by 1136
Abstract
The title compound was synthesized in near quantitative yields via initial nucleophilic aromatic substitution of pentafluoropyridine (PFP) with 4-(2-bromoethyl)phenol as a versatile precursor for ionic liquids (ILs). The purity and structure were determined using 1H, 13C, and 19F NMR and GC-EIMS. Full article
(This article belongs to the Collection Heterocycle Reactions)
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Scheme 1

5 pages, 2375 KiB  
Short Note
2,8-Dibromo-6H,12H-6,12-epoxydibenzo[b,f][1,5]dioxocine
by R. Alan Aitken, David B. Cordes, An Jie Ler and Aidan P. McKay
Molbank 2023, 2023(3), M1729; https://doi.org/10.3390/M1729 - 19 Sep 2023
Viewed by 934
Abstract
The title dibromodisalicylaldehyde, obtained as a by-product in the m-chloroperoxybenzoic acid oxidation of 5-bromo-2-(methoxymethoxy)benzaldehyde, has been characterised by IR and NMR spectroscopy and X-ray diffraction. The structure features two independent molecules with a π–π stacking interaction between them. Full article
(This article belongs to the Collection Molecules from Side Reactions)
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Graphical abstract

5 pages, 1797 KiB  
Short Note
tert-Butyl N-Hydroxycarbamate (N-Boc-Hydroxylamine)
by R. Alan Aitken, David B. Cordes, Aidan P. McKay and Dheirya K. Sonecha
Molbank 2023, 2023(3), M1728; https://doi.org/10.3390/M1728 - 18 Sep 2023
Viewed by 1018
Abstract
The X-ray structure of the title compound has been determined for the first time. This features ribbons formed by two parallel chains of molecules joined by C=O···H–N hydrogen bonding, which are then cross-linked by C=O···H–O hydrogen bonds. The structure is compared to those [...] Read more.
The X-ray structure of the title compound has been determined for the first time. This features ribbons formed by two parallel chains of molecules joined by C=O···H–N hydrogen bonding, which are then cross-linked by C=O···H–O hydrogen bonds. The structure is compared to those of closely related compounds. Full article
(This article belongs to the Section Structure Determination)
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9 pages, 1794 KiB  
Communication
(E)-3-Heptyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium Iodide as Solvatochromic and Fluorogenic Dye for Spectroscopy Applications
by Aleksey A. Vasilev, Meglena I. Kandinska, Anton Kostadinov, Laura Dietz and Stanislav Baluschev
Molbank 2023, 2023(3), M1727; https://doi.org/10.3390/M1727 - 18 Sep 2023
Viewed by 1096
Abstract
The development of new selective fluorogenic probes for monitoring microbiological objects and cellular compartments may help to determine the mechanism of pathogenesis of new pathogens in living cells. The easy and reliable synthetic strategy for the direct preparation of chemically pure styryl dye [...] Read more.
The development of new selective fluorogenic probes for monitoring microbiological objects and cellular compartments may help to determine the mechanism of pathogenesis of new pathogens in living cells. The easy and reliable synthetic strategy for the direct preparation of chemically pure styryl dye (E)-3-heptyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium iodide is described. The photophysical properties in different solvents and in water medium neat and in the presence of the dsDNA and RNA of the dye is demonstrated and compared with that of the known structure analogue. The cellular uptake and the ability to bind cell organelles is determined. The introduction of a heptyl substituent attached to the quaternary nitrogen atom of the benzothiazole ring leads to an improvement in the photophysical properties of the dye. Full article
(This article belongs to the Section Organic Synthesis)
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6 pages, 2782 KiB  
Short Note
trans-3-Benzyloxycarbonylamino-1-methyl-3-(methylcarbamoyl)azetidine-1-oxide
by Dayi Liu, Régis Guillot, Sylvie Robin and David J. Aitken
Molbank 2023, 2023(3), M1726; https://doi.org/10.3390/M1726 - 15 Sep 2023
Viewed by 1056
Abstract
trans-3-Benzyloxycarbonylamino-1-methyl-3-(methylcarbamoyl)azetidine-1-oxide was prepared by stereoselective oxidation of the corresponding azetidine precursor. The stable molecule was characterized in a low-polarity solution by IR, 1H-NMR and 13C-NMR, and in the solid state as a co-crystal with water by X-Ray diffraction. The N [...] Read more.
trans-3-Benzyloxycarbonylamino-1-methyl-3-(methylcarbamoyl)azetidine-1-oxide was prepared by stereoselective oxidation of the corresponding azetidine precursor. The stable molecule was characterized in a low-polarity solution by IR, 1H-NMR and 13C-NMR, and in the solid state as a co-crystal with water by X-Ray diffraction. The N-oxide function made a strong intramolecular 7-membered ring hydrogen bond with the methyl amide NH in solution and formed an intermolecular H-bond with the carbamate NH in a neighboring molecule in the solid state. Full article
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5 pages, 1223 KiB  
Communication
Synthesis and Characterization of 2-(((2,7-Dihydroxynaphthalen-1-yl)methylene)amino)-3′,6′-bis(ethylamino)-2′,7′-dimethylspiro[isoindoline-1,9′-xanthen]-3-one and Colorimetric Detection of Uranium in Water
by Rahisa Mohammed, Peace Ogadi, Dennis M. Seth, Jr., Amrutaa Vibho, Sarah K. Gallant and Rory Waterman
Molbank 2023, 2023(3), M1725; https://doi.org/10.3390/M1725 - 15 Sep 2023
Viewed by 1112
Abstract
2-(((2,7-Dihydroxynaphthalen-1-yl)methylene)amino)-3′,6′-bis(ethylamino)-2′,7′-dimethylspiro[isoindoline-1,9′-xanthen]-3-one was synthesized using Rhodamine 6G hydrazide (prepared using literature methods) and commercially available 2,7-dihydroxynaphthalene-1-carbaldehyde via imine condensation. Structural characterization was performed using FT-IR, 1H-NMR, 13C-NMR, X-ray, and HRMS. This Schiff base shows promise as a ligand for the colorimetric analysis [...] Read more.
2-(((2,7-Dihydroxynaphthalen-1-yl)methylene)amino)-3′,6′-bis(ethylamino)-2′,7′-dimethylspiro[isoindoline-1,9′-xanthen]-3-one was synthesized using Rhodamine 6G hydrazide (prepared using literature methods) and commercially available 2,7-dihydroxynaphthalene-1-carbaldehyde via imine condensation. Structural characterization was performed using FT-IR, 1H-NMR, 13C-NMR, X-ray, and HRMS. This Schiff base shows promise as a ligand for the colorimetric analysis of uranium in water. Full article
(This article belongs to the Section Structure Determination)
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9 pages, 2372 KiB  
Short Note
[6-(Furan-2-yl)-2,2′-bipyridine]bis(triphenylphosphine) Copper(I) Tetrafluoroborate
by Panagiotis Kouvatsis, Dimitrios Glykos, John C. Plakatouras and Gerasimos Malandrinos
Molbank 2023, 2023(3), M1724; https://doi.org/10.3390/M1724 - 13 Sep 2023
Viewed by 990
Abstract
A new heteroleptic Cu(I) complex, [Cu(L)(PPh3)2][BF4] (L = 6-(furan-2-yl)-2,2′-bipyridine; PPh3 = triphenylphosphine), was successfully synthesized and characterized. Its molecular structure was determined using X-ray crystallography, and NMR as well as HR-ESI-MS data confirm the compound’s integrity [...] Read more.
A new heteroleptic Cu(I) complex, [Cu(L)(PPh3)2][BF4] (L = 6-(furan-2-yl)-2,2′-bipyridine; PPh3 = triphenylphosphine), was successfully synthesized and characterized. Its molecular structure was determined using X-ray crystallography, and NMR as well as HR-ESI-MS data confirm the compound’s integrity in solution. The complex exhibits emission solely in the solid state (λem = 576 nm) and demonstrates a photoluminescence quantum yield of 2.5%. Full article
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8 pages, 2218 KiB  
Communication
Supramolecular Self-Assembly of the Zwitterionic Sn(IV)-Porphyrin Complex
by Nirmal Kumar Shee and Hee-Joon Kim
Molbank 2023, 2023(3), M1723; https://doi.org/10.3390/M1723 - 12 Sep 2023
Viewed by 913
Abstract
[Sn(OSO3)2(TPyHP)](HSO4)2∙8H2O (1), an ionic Sn(IV)-porphyrin complex, was prepared by reacting [Sn(OH2)2TPyP] with dilute sulfuric acid. X-ray structural analysis revealed that the zwitterionic [Sn(OSO3) [...] Read more.
[Sn(OSO3)2(TPyHP)](HSO4)2∙8H2O (1), an ionic Sn(IV)-porphyrin complex, was prepared by reacting [Sn(OH2)2TPyP] with dilute sulfuric acid. X-ray structural analysis revealed that the zwitterionic [Sn(OSO3)2TPyHP]2+ species consists of two anionic axial Sn–O–SO3 units and four peripheral pyridinium moieties, with an overall dicationic charge balanced by two hydrogen sulfate (HSO4−) counter-anions. Ionic hydrogen bonding between the oxygen atoms of axial sulfato ligands and the peripheral pyridinium groups of adjacent Sn(IV)-porphyrin cations led to the formation of a 1D channel filled with counter-anions and water molecules. The supramolecular self-assembly of 1 was further characterized using various spectroscopic techniques, including 1H NMR spectroscopy, elemental analysis, ESI-mass spectrometry, UV-vis spectroscopy, fluorescence spectroscopy, FT-IR spectroscopy, thermogravimetric analysis (TGA), and powder X-ray diffractometry. The zwitterionic [Sn(OSO3)2TPyHP]2+ complex is a structurally well-defined complementary scaffold involved in supramolecular self-assembly. This novel class of ion-assembled metalloporphyrin is a potential functional porphyrin material used in ion exchange applications. Full article
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9 pages, 5634 KiB  
Short Note
Cocrystal of Codeine and Cyclopentobarbital
by Thomas Gelbrich, Jascha Schinke and Ulrich J. Griesser
Molbank 2023, 2023(3), M1722; https://doi.org/10.3390/M1722 - 11 Sep 2023
Viewed by 1161
Abstract
The two-component compound formed by codeine and cyclopentobarbital was produced using grinding techniques and through evaporation from alcoholic solutions. The cocrystal nature of this phase was established unequivocally through single crystal X-ray structure determination. The asymmetric unit contains one formula unit. In the [...] Read more.
The two-component compound formed by codeine and cyclopentobarbital was produced using grinding techniques and through evaporation from alcoholic solutions. The cocrystal nature of this phase was established unequivocally through single crystal X-ray structure determination. The asymmetric unit contains one formula unit. In the cyclopentobarbital molecule, the cyclopentenyl ring is disordered over two positions related by a rotation of approximately 180° about its C—C bond to the pyrimidine ring. The two NH groups of the cyclopentobarbital molecule form N—H⋯N and N—H⋯O bonds to piperidine and hydroxyl groups, respectively, belonging to different codeine molecules. In addition, the hydroxyl and methoxy groups of neighboring codeine molecules are linked by O—H⋯O interactions, resulting in a H-bonded framework structure of codeine and cyclopentobarbital molecules. The cocrystal was also characterized using thermal analysis, X-ray powder diffraction and IR spectroscopy. Full article
(This article belongs to the Section Structure Determination)
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Graphical abstract

7 pages, 938 KiB  
Short Note
4a′-Hydroxy-3′,3′,5,6′,6′,7-hexamethyl-3′,4′,4a′,6′,7′,9a′-hexahydrospiro[indole-3,9′-xanthene]-1′,2,8′(1H,2′H,5′H)-trione
by Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Fedor V. Ryzhkov, Artem N. Fakhrutdinov and Michail N. Elinson
Molbank 2023, 2023(3), M1721; https://doi.org/10.3390/M1721 - 8 Sep 2023
Viewed by 863
Abstract
Pseudo-multicomponent reactions (Pseudo-MCRs) have led to a variety of compounds with interesting biological properties, especially desirable in the pharmaceutical industry. The isatin nucleus could be considered a privileged scaffold for the design of biologically active substances. Dimedone is an interesting and versatile molecule [...] Read more.
Pseudo-multicomponent reactions (Pseudo-MCRs) have led to a variety of compounds with interesting biological properties, especially desirable in the pharmaceutical industry. The isatin nucleus could be considered a privileged scaffold for the design of biologically active substances. Dimedone is an interesting and versatile molecule for most organic transformations, especially one-pot and multicomponent reactions. Xanthene derivatives are still an attractive research field for both academia investigations and industry. In this investigation, a simple and efficient tandem Knoevenagel–Michael protocol with subsequent cyclization for the synthesis of the previously unknown 4a′-hydroxy-3′,3′,5,6′,6′,7-hexamethyl-3′,4′,4a′,6′,7′,9a′-hexahydrospiro[indole-3,9′-xanthene]-1′,2,8′(1H,2′H,5′H)-trione was elaborated. The suggested method is based on the pseudo-MCR of 5,7-dimethylisatin and dimedone. The structure of the earlier unknown compound was proven using 1H, 13C-NMR, and IR spectroscopy, mass spectrometry, and elemental analysis. To compare the developed protocol with the existing ones, unsubstituted spiro[indole-3,9′-xanthene] was synthesized. Its structure has been proven using two-dimensional (2D) NMR spectroscopy techniques. Full article
(This article belongs to the Section Organic Synthesis)
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Figure 1

5 pages, 1266 KiB  
Short Note
2-((4-Amino-5-((2,4-dichlorophenoxy)methyl)-4H-1,2,4-triazol-3-yl)thio)-1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one
by Bakr F. Abdel-Wahab, Ahmed F. Mabied, James C. Fettinger and Abdelbasset A. Farahat
Molbank 2023, 2023(3), M1720; https://doi.org/10.3390/M1720 - 6 Sep 2023
Viewed by 921
Abstract
The reaction of 2-bromo-1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one (1) with 4-amino-5-((2,4-dichlorophenoxy)methyl)-4H-1,2,4-triazole-3-thiol (2) in absolute ethanol in the presence of triethyl amine as catalyst gave 2-((4-amino-5-((2,4-dichlorophenoxy)methyl)-4H-1,2,4-triazol-3-yl)thio)-1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one (3) in 73% yield. The structure of the [...] Read more.
The reaction of 2-bromo-1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one (1) with 4-amino-5-((2,4-dichlorophenoxy)methyl)-4H-1,2,4-triazole-3-thiol (2) in absolute ethanol in the presence of triethyl amine as catalyst gave 2-((4-amino-5-((2,4-dichlorophenoxy)methyl)-4H-1,2,4-triazol-3-yl)thio)-1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one (3) in 73% yield. The structure of the title heterocycle (3) was confirmed by X-ray single crystal diffraction and spectral analyses (NMR and IR). Full article
(This article belongs to the Section Structure Determination)
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Figure 1

8 pages, 1286 KiB  
Communication
Mono- and Dinuclear Carbonyl Dithiolene Complexes Related to the [FeFe]-Hydrogenases
by Mohamed Kdider, Catherine Elleouet, François Y. Pétillon and Philippe Schollhammer
Molbank 2023, 2023(3), M1719; https://doi.org/10.3390/M1719 - 6 Sep 2023
Viewed by 920
Abstract
The di-iron carbonyl dithiolene bridged complex [Fe2(CO)6(µ-S2C2(CO2Me)2)] (1) reacts with 1 equivalent of phosphane PR3 (R = Ph, OMe) to give, as major products, monosubstituted derivatives [...] Read more.
The di-iron carbonyl dithiolene bridged complex [Fe2(CO)6(µ-S2C2(CO2Me)2)] (1) reacts with 1 equivalent of phosphane PR3 (R = Ph, OMe) to give, as major products, monosubstituted derivatives [Fe2(CO)5L(µ-S2C2(CO2Me)2)] (L = PPh3 (2), P(OMe)3 (3)). In the presence of an excess (3–4 equiv.) of P(OMe)3, the cleavage of 1 arises partly and a mixture of the mononuclear species [Fe(CO)(P(OMe)3)2(κ2-S2C2(CO2Me)2)] (4) and 3 is obtained. The compounds 2–4 were analyzed by IR and 1H, 31P-{1H} NMR spectroscopies. Their structures in solid state were determined by X-ray diffraction analyses, which accord with their spectroscopic characteristics. Full article
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Figure 1

6 pages, 1233 KiB  
Communication
Synthesis of N1-(3,5-Bis(trifluoromethyl)benzyl)benzene-1,2-diamine and N,N-Bis(2-nitrophenyl)-3,5-bis(trifluoromethyl)aniline
by Luka Ciber, Helena Brodnik, Franc Požgan, Jurij Svete, Bogdan Štefane and Uroš Grošelj
Molbank 2023, 2023(3), M1718; https://doi.org/10.3390/M1718 - 4 Sep 2023
Viewed by 898
Abstract
A monosubstituted benzene-1,2-diamine building block, N1-(3,5-bis(trifluoromethyl)benzyl)benzene-1,2-diamine, was prepared in two steps from commercially available 3,5-bis(trifluoromethyl)benzylamine and 1-fluoro-2-nitrobenzene, while the use of 3,5-bis(trifluoromethyl)aniline as the starting amine gave a triarylamine, N,N-bis(2-nitrophenyl)-3,5-bis(trifluoromethyl)aniline. The structures of the newly synthesized compounds were fully characterized. Full article
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Figure 1

7 pages, 1423 KiB  
Short Note
N-(2,3-Difluorophenyl)-2-fluorobenzamide
by Niall Hehir and John F. Gallagher
Molbank 2023, 2023(3), M1717; https://doi.org/10.3390/M1717 - 1 Sep 2023
Cited by 1 | Viewed by 1048
Abstract
The title compound N-(2,3-difluorophenyl)-2-fluorobenzamide or (Fo23) was obtained at high yield (88%) from the condensation reaction of 2-fluorobenzoyl chloride with 2,3-difluoroaniline using standard synthetic procedures. The crystal structure of Fo23 was determined at 294 (1) K using single crystal X-ray [...] Read more.
The title compound N-(2,3-difluorophenyl)-2-fluorobenzamide or (Fo23) was obtained at high yield (88%) from the condensation reaction of 2-fluorobenzoyl chloride with 2,3-difluoroaniline using standard synthetic procedures. The crystal structure of Fo23 was determined at 294 (1) K using single crystal X-ray diffraction methods and represents the first regular tri-fluorinated benzamide with formula C13H8F3NO compared to the difluorinated and tetra-fluorinated analogues. In the structure, both aromatic rings are effectively co-planar, with an interplanar angle of 0.5(2)°; however, the central amide group plane is oriented by 23.17(18)° and 23.44(17)° from the aromatic rings as influenced by 1D amide⋯amide hydrogen bonds along the a-axis direction. Longer C-H⋯F/O interactions and the arrangement of a R22(12) synthon involving two C-F, a N-H and two C-H, together with C-F⋯C ring⋯ring stacking contacts, complete the interactions in the Fo23 crystal structure. Full article
(This article belongs to the Section Structure Determination)
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Figure 1

7 pages, 1748 KiB  
Short Note
(2R,4aS,6aS,12bR,14aS,14bR)10-Hydroxy-N-(4-((6-methoxyquinolin-8-yl)amino)pentyl)-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 Yuhan Xie, Houin Kuan, Qin Wei, Alessandra Gianoncelli, Giovanni Ribaudo and Paolo Coghi
Molbank 2023, 2023(3), M1716; https://doi.org/10.3390/M1716 - 29 Aug 2023
Cited by 1 | Viewed by 1075
Abstract
We herein report the synthesis of a derivative of the natural compound celastrol linked to the antimalarial drug primaquine through an amide obtained by the activation of the carboxylic acid with HOBt/EDC. The chemical structure of the new molecule was fully characterized by [...] Read more.
We herein report the synthesis of a derivative of the natural compound celastrol linked to the antimalarial drug primaquine through an amide obtained by the activation of the carboxylic acid with HOBt/EDC. The chemical structure of the new molecule was fully characterized by proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), heteronuclear single quantum coherence (HSQC), correlation spectroscopy (1H-1H-COSY), distortionless enhancement by polarization transfer (DEPT), mass spectrometry, Fourier-transform infrared (FTIR), and ultraviolet (UV) spectroscopies. Computational studies were enrolled to predict the interaction of the synthesized compound with sarco-endoplasmic reticulum (SR) Ca2+ transport ATPase (SERCA), a target of relevance for developing new therapeutics against arthritis. The drug-likeness of the compound was also investigated by predicting its pharmacokinetic properties. Full article
(This article belongs to the Section Organic Synthesis)
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6 pages, 1121 KiB  
Communication
Synthesis of a Novel 2-((4,5-Diphenyl-4H-1,2,4-triazol-3-yl)thio)acetaldehyde as a Bisulfite Adduct
by Beniamin-Nicolae Pintea, Ion Burcă, Valentin Badea and Francisc Peter
Molbank 2023, 2023(3), M1715; https://doi.org/10.3390/M1715 - 24 Aug 2023
Viewed by 976
Abstract
The scope of the current work was to synthesize an S-alkylated 1,2,4-triazole-3-thiol derivative. Synthesis was carried out in two steps: in the first step, 4,5-diphenyl-4H-1,2,4-triazole-3-thiol was S-alkylated using a halogenated acetal and cesium carbonate. In the second step, several [...] Read more.
The scope of the current work was to synthesize an S-alkylated 1,2,4-triazole-3-thiol derivative. Synthesis was carried out in two steps: in the first step, 4,5-diphenyl-4H-1,2,4-triazole-3-thiol was S-alkylated using a halogenated acetal and cesium carbonate. In the second step, several acetal deprotection procedures were tested, and the aldehyde obtained was isolated as a bisulfite adduct. The structures of the new compounds were characterized by FT-IR, 1D, and 2D NMR spectroscopic methods. Full article
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Graphical abstract

7 pages, 1753 KiB  
Short Note
(E)-2-(6-(4′-(Diphenylamino)-[1,1′-biphenyl]-2-yl)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5(4H)-ylidene)-2-(6-(4′-(diphenylamino)-[1,1′-biphenyl]-2-yl)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl)acetonitrile
by Yuriy A. Kvashnin, Pavel A. Slepukhin, Denis A. Gazizov, Ekaterina F. Zhilina, Gennady L. Rusinov, Egor V. Verbitskiy and Valery N. Charushin
Molbank 2023, 2023(3), M1714; https://doi.org/10.3390/M1714 - 21 Aug 2023
Viewed by 994
Abstract
[1,2,5]Oxadiazolo[3,4-b]pyrazines are of great interest due to their promising photophysical and electrochemical properties, as well their potential use in a wide range of electronic devices. Herein, we report on the preparation of the unexpected product derived from the interaction of 2′-([1,2,5]oxadiazolo[3,4- [...] Read more.
[1,2,5]Oxadiazolo[3,4-b]pyrazines are of great interest due to their promising photophysical and electrochemical properties, as well their potential use in a wide range of electronic devices. Herein, we report on the preparation of the unexpected product derived from the interaction of 2′-([1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl)-N,N-diphenyl-[1,1′-biphenyl]-4-amine with 2-cyanoacetic acid under basic conditions. The resulting product was characterized using 1H and 13C NMR spectra, high resolution mass spectrometry, Fourier-transform infrared spectroscopy (FTIR), and X-ray diffraction analyses. Furthermore, its photophysical and electrochemical properties were studied using cyclic voltammetry, UV–Vis, and emission spectroscopy. The experimental results have been further rationalized through theoretical DFT calculations. Full article
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Figure 1

5 pages, 770 KiB  
Communication
Synthesis of a New α-Azidomethyl Styrene from Safrole via a Dearomative Rearrangement
by Stephen R. Isbel and Alejandro Bugarin
Molbank 2023, 2023(3), M1713; https://doi.org/10.3390/M1713 - 16 Aug 2023
Cited by 1 | Viewed by 972
Abstract
There is a growing interest in developing more efficient synthetic alternatives for the synthesis of nitrogen-containing allylic compounds. This article presents a straightforward two-step protocol to produce 5-(3-azidoprop-1-en-2-yl)benzo[d][1,3]dioxole 4 from the natural product safrole. The method yielded the expected α-azidomethyl styrene [...] Read more.
There is a growing interest in developing more efficient synthetic alternatives for the synthesis of nitrogen-containing allylic compounds. This article presents a straightforward two-step protocol to produce 5-(3-azidoprop-1-en-2-yl)benzo[d][1,3]dioxole 4 from the natural product safrole. The method yielded the expected α-azidomethyl styrene 4, in good yield, via a dearomative rearrangement. Full article
(This article belongs to the Section Organic Synthesis)
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Scheme 1

6 pages, 1076 KiB  
Communication
Friedländer-Type Reaction of 4-Cholesten-3-one with 2′-Aminoacetophenone: Angular versus Linear Quinoline-Fused Steroids
by Caterina Momoli, Valerio Morlacci, Marco Chiarini, Laura Palombi and Antonio Arcadi
Molbank 2023, 2023(3), M1712; https://doi.org/10.3390/M1712 - 16 Aug 2023
Viewed by 925
Abstract
To optimize the experimental conditions used for the Friedländer-type condensation, an angular fused 4-substituted quinoline steroid has been obtained in very high yield and regioselectivity using readily available 4-cholesten-3-one and 2′-aminoacetophenone. Moreover, by varying the reaction conditions and the catalyst, the corresponding linear [...] Read more.
To optimize the experimental conditions used for the Friedländer-type condensation, an angular fused 4-substituted quinoline steroid has been obtained in very high yield and regioselectivity using readily available 4-cholesten-3-one and 2′-aminoacetophenone. Moreover, by varying the reaction conditions and the catalyst, the corresponding linear regioisomer was also achieved with an acceptable isolated yield and high chemoselectivity. Both structures have been definitively elucidated via 2D-NMR and fully characterized. Full article
(This article belongs to the Section Organic Synthesis)
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4 pages, 877 KiB  
Short Note
Pentapotassium Bis(hydrogenphospate) Dihydrogenphospate Monohydrate
by Camila Caro Garrido, Tom Leyssens and Koen Robeyns
Molbank 2023, 2023(3), M1711; https://doi.org/10.3390/M1711 - 14 Aug 2023
Viewed by 835
Abstract
The structure of K5(HPO4)2(H2PO4)·H2O was determined via single crystal diffraction. The crystal structures of phosphate salts of potassium have been known since the early days of crystallography. Here, we present a new monohydrate adduct between K2HPO4 and KH2PO4. Full article
(This article belongs to the Section Structure Determination)
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Graphical abstract

11 pages, 1812 KiB  
Short Note
Tributyl(1-((dimethylamino)(dimethyliminio)methyl)-1,4-dihydropyridin-4-yl)phosphonium Ditrifluoromethanesulfonate
by Yiwei Gong, Jas S. Ward, Kari Rissanen and Florian F. Mulks
Molbank 2023, 2023(3), M1710; https://doi.org/10.3390/M1710 - 9 Aug 2023
Cited by 2 | Viewed by 1228
Abstract
Site-selective functionalization of pyridines is a crucial tool for the synthesis of diverse pharmaceuticals and materials. We introduced diiminium pyridine adducts as highly convenient and potent Lewis acids. We report that tributylphosphine selectively adds to the 4-position of pyridine in tetramethyldiiminium pyridine ditrifluoromethanesulfonate, [...] Read more.
Site-selective functionalization of pyridines is a crucial tool for the synthesis of diverse pharmaceuticals and materials. We introduced diiminium pyridine adducts as highly convenient and potent Lewis acids. We report that tributylphosphine selectively adds to the 4-position of pyridine in tetramethyldiiminium pyridine ditrifluoromethanesulfonate, resulting in the formation of the title compound. This finding represents an advancement towards the utilization of diiminium units as organic reagents or catalysts for pyridine functionalization. We also employ computational models to determine fluoride and hydride ion affinities, Fukui function f+(r), molecular electrostatic potential, and pKa values, providing valuable insights for future investigations in this area. Full article
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Figure 1

4 pages, 965 KiB  
Short Note
(E)-2-(1,3-Diphenylallyl)-3,5-dimethoxyphenol
by Lara Mollà-Guerola and Alejandro Baeza
Molbank 2023, 2023(3), M1709; https://doi.org/10.3390/M1709 - 4 Aug 2023
Viewed by 876
Abstract
The synthesis of (E)-2-(1,3-diphenylallyl)-3,5-dimethoxyphenol is described by means of the reaction of 3,5-dimethoxyphenol with (E)-1,3-diphenylprop-2-en-1-ol in 1,1,1,3,3,3-hexafluoroispropanol (HFIP), which acts as a solvent and reaction promoter. The reaction proceeds smoothly to afford the mentioned compound in high yield under [...] Read more.
The synthesis of (E)-2-(1,3-diphenylallyl)-3,5-dimethoxyphenol is described by means of the reaction of 3,5-dimethoxyphenol with (E)-1,3-diphenylprop-2-en-1-ol in 1,1,1,3,3,3-hexafluoroispropanol (HFIP), which acts as a solvent and reaction promoter. The reaction proceeds smoothly to afford the mentioned compound in high yield under a metal and additive-free procedure. The corresponding allylated phenol has been fully characterized. Full article
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Figure 1

5 pages, 485 KiB  
Short Note
Isoamyl (E)-3-(3,4-Dimethoxyphenyl)acrylate
by Egar Pamela, Lukman Atmaja and Mardi Santoso
Molbank 2023, 2023(3), M1708; https://doi.org/10.3390/M1708 - 2 Aug 2023
Viewed by 855
Abstract
Isoamyl (E)-3-(3,4-dimethoxyphenyl)acrylate (1) was obtained from the 2-methyl-6-nitrobenzoic anhydride (MNBA)/4-dimethylaminopyridine (DMAP)-catalyzed reaction at room temperature for 190 min in dichloromethane with a yield of 95%. The structure of isoamyl (E)-3-(3,4-dimethoxyphenyl)acrylate (1) was elucidated using NMR, [...] Read more.
Isoamyl (E)-3-(3,4-dimethoxyphenyl)acrylate (1) was obtained from the 2-methyl-6-nitrobenzoic anhydride (MNBA)/4-dimethylaminopyridine (DMAP)-catalyzed reaction at room temperature for 190 min in dichloromethane with a yield of 95%. The structure of isoamyl (E)-3-(3,4-dimethoxyphenyl)acrylate (1) was elucidated using NMR, FTIR, and high-resolution mass spectrometry. In vitro sun protection factor evaluation exhibited a value of 37.10 ± 0.03 which indicates that isoamyl (E)-3-(3,4-dimethoxyphenyl)acrylate (1) is a sunscreen agent with high protection. Full article
(This article belongs to the Section Organic Synthesis)
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Scheme 1

5 pages, 364 KiB  
Communication
Synthesis of Novel Diterpenic Peptides via the Ugi Reaction and Their Anticancer Activities
by Anna A. Smirnova, Liana M. Zakirova, Irina E. Smirnova and Elena V. Tretyakova
Molbank 2023, 2023(3), M1707; https://doi.org/10.3390/M1707 - 1 Aug 2023
Viewed by 828
Abstract
Novel diterpenic peptide derivatives were synthesized via the Ugi four-component reaction at ambient temperature. The protocol employed a reaction between formaldehyde, benzyl amine, the corresponding diterpene acid, and ethyl 2-isocyanoacetate. The anticancer properties of the compounds were studied in vitro. Full article
(This article belongs to the Section Organic Synthesis)
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Scheme 1

5 pages, 1439 KiB  
Short Note
N′-(5-Bromofuran-2-carbonyl)isonicotinohydrazide
by Ersya Yanu Ramadhani, Nur Pasca Aijijiyah, Eko Santoso, Lukman Atmaja and Mardi Santoso
Molbank 2023, 2023(3), M1706; https://doi.org/10.3390/M1706 - 1 Aug 2023
Viewed by 947
Abstract
N′-(5-bromofuran-2-carbonyl)isonicotinohydrazide (1) was obtained in the form of a colorless solid from the 2-methyl-6-nitrobenzoic anhydride (MNBA)/4-dimethylaminopyridine (DMAP)-catalyzed reaction of 5-bromofuran-2-carboxylic acid and isoniazid in dichloromethane at room temperature with a yield of 83%. The structure of N′-(5-bromofuran-2-carbonyl)isonicotinohydrazide (1 [...] Read more.
N′-(5-bromofuran-2-carbonyl)isonicotinohydrazide (1) was obtained in the form of a colorless solid from the 2-methyl-6-nitrobenzoic anhydride (MNBA)/4-dimethylaminopyridine (DMAP)-catalyzed reaction of 5-bromofuran-2-carboxylic acid and isoniazid in dichloromethane at room temperature with a yield of 83%. The structure of N′-(5-bromofuran-2-carbonyl)isonicotinohydrazide (1) was elucidated using 1H NMR, 13C NMR, FTIR, and high-resolution mass spectrometry. Molecular docking screening of the title compound (1) on cyclooxygenase-2 (COX-2) protein (PDB ID: 5IKR) indicated that compound (1) has a good binding affinity, suggesting that further structure optimization and in-depth research can be carried out on compound (1) as a potential COX-2 inhibitor. Full article
(This article belongs to the Section Organic Synthesis)
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7 pages, 609 KiB  
Short Note
4-(4-Ethoxyphenyl)-5-(4-methoxyphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one
by Ion Burcă, Valentin Badea, Calin Deleanu, Vasile-Nicolae Bercean and Francisc Péter
Molbank 2023, 2023(3), M1705; https://doi.org/10.3390/M1705 - 1 Aug 2023
Viewed by 915
Abstract
A new triazol-3-one resulted unexpectedly from the reduction reaction of a heterocyclic thioketone using sodium borohydride in pyridine containing a small amount of water. The structure of the new compound was characterised using FT-IR, 1D and 2D NMR, and HRMS spectroscopic methods. Full article
(This article belongs to the Collection Molecules from Side Reactions)
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Graphical abstract

7 pages, 555 KiB  
Communication
N-(((1S,5R)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)-3-dodecan/tetradecanamido-N,N-dimethylpropan-1-aminium Bromide
by Liliya E. Nikitina, Ilmir R. Gilfanov, Roman S. Pavelyev, Svetlana A. Lisovskaya, Elena Y. Trizna, Ilfat Z. Rakhmatullin, Vladimir V. Klochkov, Rustam R. Davletshin, Olga B. Babaeva, Alena I. Kolesnikova, Olga V. Ostolopovskaya, Larisa L. Frolova and Airat R. Kayumov
Molbank 2023, 2023(3), M1704; https://doi.org/10.3390/M1704 - 26 Jul 2023
Viewed by 964
Abstract
The syntheses of the title compounds were performed using lauric and myristic acids. The compounds obtained were characterized using 1H-, 13C-NMR and 2D 1H-1H COSY, 1H-13C HSQC NMR, IR, and high-resolution mass spectrometry. Both compounds [...] Read more.
The syntheses of the title compounds were performed using lauric and myristic acids. The compounds obtained were characterized using 1H-, 13C-NMR and 2D 1H-1H COSY, 1H-13C HSQC NMR, IR, and high-resolution mass spectrometry. Both compounds exhibited bactericidal activity on S. aureus comparable to that of a reference drug (miramistin). Compound 10, with lauric acid fragment, had a 16-fold higher activity on P. aeruginosa compared to compound 11, which in turn contains myristic acid fragment (with minimum inhibitory concentrations of 32 and 512 μg/mL, respectively). Compound 11 exhibited a pronounced activity against all types of fungi (higher than the activity of miramistin), while the activity of compound 10 was considerably lower. Thus, compound 11 can serve as a promising antimicrobial agent for the treatment of various fungal and staphylococcal infections, while compound 10 is of interest to treat P. aeruginosa-associated infections. Full article
(This article belongs to the Section Organic Synthesis)
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5 pages, 1263 KiB  
Short Note
2,7-Bis(pyridin-4-ylethynyl)-9H-carbazole
by Enrico Podda, Massimiliano Arca, Anna Pintus, Vito Lippolis, Giulio Ferino, James B. Orton, Simon J. Coles and Maria Carla Aragoni
Molbank 2023, 2023(3), M1703; https://doi.org/10.3390/M1703 - 24 Jul 2023
Cited by 1 | Viewed by 814
Abstract
2,7-Bis(pyridin-4-ylethynyl)-9H-carbazole (1) was synthesized by reacting 4-ethynylpyridine hydrochloride with 2,7-dibromo-9H-carbazole. The full characterization of compound 1 is presented, and the crystal structure of its monohydrate was determined by single-crystal XRD analysis. Full article
(This article belongs to the Section Structure Determination)
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Graphical abstract

5 pages, 683 KiB  
Short Note
6,7-Dihydroxy-5,8-dimethoxy-2H-chromen-2-one
by Olga I. Adaeva, Dmitry V. Demchuk and Victor V. Semenov
Molbank 2023, 2023(3), M1702; https://doi.org/10.3390/M1702 - 23 Jul 2023
Cited by 2 | Viewed by 997
Abstract
This article presents a novel approach for synthesizing a new 5,8-dimethoxy derivative of esculetin via the selective cleavage of the methylene bridge in sabandin—naturally occurring and easily synthetically accessible methoxylated coumarin. A high selectivity is achieved by using acetoxylation of methylenedioxy group with [...] Read more.
This article presents a novel approach for synthesizing a new 5,8-dimethoxy derivative of esculetin via the selective cleavage of the methylene bridge in sabandin—naturally occurring and easily synthetically accessible methoxylated coumarin. A high selectivity is achieved by using acetoxylation of methylenedioxy group with lead tetraacetate. Natural coumarin sabandin as a starting compound was prepared in a few simple steps from 5-allyl-4,7-dimethoxybenzo[d][1,3]dioxole (apiol), which is readily available from parsley and dill seed extracts. The developed method enables an efficient and straightforward synthesis of a new derivative of esculetin with potential medicinal and therapeutic applications. Full article
(This article belongs to the Section Organic Synthesis)
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