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Molbank
Volume 2023
Issue 2
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Molbank, Volume 2023, Issue 2 (June 2023) – 66 articles

Cover Story (view full-size image): Benzofurans, also known by users as "Benzo Furys", are synthetic phenethylamines, a growing group of designer drugs that belong to the so-called novel psychoactive substances (NPS) group. Some recent research work reported that the toxicity of benzo fury is beginning to emerge, revealing an alarming public health threat regarding the abuse of these NPS. Highlighting the need for a better understanding of their pharmacodynamics and toxicity regarding the synthesis of metabolites is of crucial importance and in this work, we present a six-step synthesis with an overall yield of 11% for one of the described 5-APB metabolites, 2-(5-(2-aminopropyl)-2-hydroxyphenyl)acetic acid. View this paper
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4 pages, 1111 KiB  
Short Note
5-[(5-Chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)methyl]-N-[[6-(trifluoromethyl)pyridin-3-yl]methyl]pyridin-2-amine Dihydrochloride Dihydrate
by Weronika Kozanecka-Okupnik, Klaus Wurst, Sandro Neuner, Sven Nerdinger and Thomas Gelbrich
Molbank 2023, 2023(2), M1673; https://doi.org/10.3390/M1673 - 19 Jun 2023
Viewed by 869
Abstract
The dihydrochloride salt of pexidartinib was synthesized and the crystal structure of its dihydrate was determined from single crystal data. The asymmetric unit consists of one formula unit. In the pexidartinib molecule, the N atom of the central pyridine ring and the pyridine-N [...] Read more.
The dihydrochloride salt of pexidartinib was synthesized and the crystal structure of its dihydrate was determined from single crystal data. The asymmetric unit consists of one formula unit. In the pexidartinib molecule, the N atom of the central pyridine ring and the pyridine-N atom of the pyrrolopyridine group are both protonated. The pexidartinib molecule forms N–H···O and N–H···Cl interactions with neighboring water molecules and chloride ions, respectively. Water/chloride (O–H···Cl) and water/water (O–H···O) interactions are also observed. Collectively, these intermolecular interactions result in a complex H-bonded framework structure. Full article
(This article belongs to the Section Structure Determination)
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Figure 1

7 pages, 1985 KiB  
Communication
Synthesis, Spectroscopic, and Thermal Analyses of 2-Oxo-1,2-dihydroquinolin-8-yl 4-chlorobenzoate
by Diana Becerra, Hugo Rojas and Juan-Carlos Castillo
Molbank 2023, 2023(2), M1672; https://doi.org/10.3390/M1672 - 19 Jun 2023
Viewed by 838
Abstract
The 2-oxo-1,2-dihydroquinolin-8-yl 4-chlorobenzoate was synthesized in good yield using a triethylamine-mediated O-acylation reaction between 8-hydroxyquinolin-2(1H)-one and 4-chlorobenzoyl chloride in acetonitrile at room temperature. This methodology is notable for its clean reaction profile and straightforward procedure. The 2-oxoquinoline derivative was characterized [...] Read more.
The 2-oxo-1,2-dihydroquinolin-8-yl 4-chlorobenzoate was synthesized in good yield using a triethylamine-mediated O-acylation reaction between 8-hydroxyquinolin-2(1H)-one and 4-chlorobenzoyl chloride in acetonitrile at room temperature. This methodology is notable for its clean reaction profile and straightforward procedure. The 2-oxoquinoline derivative was characterized using spectroscopic, spectrometric, and thermal analyses, enabling a comprehensive understanding of its molecular structure and thermal properties. Full article
(This article belongs to the Collection Heterocycle Reactions)
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Figure 1

6 pages, 1896 KiB  
Short Note
(Decacarbonyl)(1-isopropyl-2-phenyl-1,2,5,6-tetrahydroacenaphtho [5,6-cd][1,2]diphosphole)ditungsten(0)
by Zachary H. Davis, Cameron L. Carpenter-Warren, Laurence J. Taylor, Alexandra M. Z. Slawin, Petr Kilian and Brian A. Chalmers
Molbank 2023, 2023(2), M1671; https://doi.org/10.3390/M1671 - 16 Jun 2023
Viewed by 936
Abstract
A binuclear tungsten(0) complex with an asymmetric bridging 1,2-diphosphole ligand was prepared by the photolysis of tungsten hexacarbonyl in the presence of 1-isopropyl-2-phenyl-1,2,5,6-tetrahydroacenaphtho [5,6-cd][1,2]diphosphole. The tungsten complex 1 was characterized by high resolution mass spectrometry, multinuclear NMR spectroscopy (1H, 13C, [...] Read more.
A binuclear tungsten(0) complex with an asymmetric bridging 1,2-diphosphole ligand was prepared by the photolysis of tungsten hexacarbonyl in the presence of 1-isopropyl-2-phenyl-1,2,5,6-tetrahydroacenaphtho [5,6-cd][1,2]diphosphole. The tungsten complex 1 was characterized by high resolution mass spectrometry, multinuclear NMR spectroscopy (1H, 13C, 31P), and elemental microanalysis. The structure of the trans isomer was resolved by single crystal X-ray diffraction, showing a slight elongation of the P−P bond upon coordination to the W(CO)5 groups. Full article
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Figure 1

7 pages, 2204 KiB  
Communication
Photoinduced Ring Opening of Methyl 1-Aryl-5-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylates in the Presence of Diaryl Disulfides
by Nejc Petek and Uroš Grošelj
Molbank 2023, 2023(2), M1670; https://doi.org/10.3390/M1670 - 15 Jun 2023
Viewed by 821
Abstract
Among the methods used for the synthesis of functionalized heterocyclic compounds, photochemistry has gained immense popularity due to the reactivity of intermediates in photoinduced reactions. In this study, we report on the effect of diaryl disulfides as hydrogen atom transfer catalysts on the [...] Read more.
Among the methods used for the synthesis of functionalized heterocyclic compounds, photochemistry has gained immense popularity due to the reactivity of intermediates in photoinduced reactions. In this study, we report on the effect of diaryl disulfides as hydrogen atom transfer catalysts on the photoinduced transformations of pyrazolo[1,2-a]pyrazolones. After excitation with visible light, these compounds are susceptible to C–N bond cleavage, followed by intermolecular hydrogen atom abstraction. By modifying the reaction conditions, we have developed two novel methods for the synthesis of highly substituted pyrazoles. Full article
(This article belongs to the Collection Heterocycle Reactions)
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Scheme 1

4 pages, 384 KiB  
Short Note
(trans-Dihydroxo)Sn(IV)-[5,10,15,20-tetrakis(2-pyridyl)porphyrin]
by Nirmal Kumar Shee and Hee-Joon Kim
Molbank 2023, 2023(2), M1669; https://doi.org/10.3390/M1669 - 14 Jun 2023
Viewed by 1073
Abstract
Sn(IV)-porphyrin complex with trans-dihydroxo axial-ligands and 2-pyridyl peripheral substituents, namely (trans-dihydroxo)[5,10,15,20-tetrakis(2-pyridyl)porphyrinato]tin(IV) was synthesized and fully characterized by various techniques such as elemental analysis, 1H NMR spectroscopy, ESI-MS spectrometry, UV-visible spectroscopy, and fluorescence spectroscopy. Full article
(This article belongs to the Section Organic Synthesis)
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Scheme 1

5 pages, 600 KiB  
Communication
Synthesis of 5-Aroyl-2-aryl-3-hydroxypyridin-4(1H)-ones
by Elena V. Steparuk, Dmitrii L. Obydennov and Vyacheslav Y. Sosnovskikh
Molbank 2023, 2023(2), M1668; https://doi.org/10.3390/M1668 - 10 Jun 2023
Cited by 1 | Viewed by 1105
Abstract
A two-stage synthesis of 5-aroyl-2-aryl-3-hydroxypyridin-4(1H)-ones (56–66% overall yields) was carried out by refluxing 5-aroyl-3-(benzyloxy)-2-(het)aryl-4H-pyran-4-ones with ammonium acetate in AcOH and subsequent debenzylation. The prepared N-unsubstituted 4-pyridones exist in the pyridone tautomeric form. Full article
(This article belongs to the Collection Heterocycle Reactions)
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Graphical abstract

5 pages, 1018 KiB  
Short Note
N-(diisopropylphosphanyl)benzamide
by María M. Alcaide, Daniel García Garrido, Eleuterio Álvarez and Riccardo Peloso
Molbank 2023, 2023(2), M1667; https://doi.org/10.3390/M1667 - 10 Jun 2023
Viewed by 1109
Abstract
N-(diisopropylphosphanyl)benzamide, PhC(O)NHPiPr2, has been synthesized in good yield following two alternative procedures that employ benzamide as the starting material. The first one is a two-step preparation, in which N-(trimetilsilyl)benzamide is reacted with PiPr2Cl [...] Read more.
N-(diisopropylphosphanyl)benzamide, PhC(O)NHPiPr2, has been synthesized in good yield following two alternative procedures that employ benzamide as the starting material. The first one is a two-step preparation, in which N-(trimetilsilyl)benzamide is reacted with PiPr2Cl to give the title compound in good yield, whereas the second one is a straightforward synthesis which converts benzamide into N-(diisopropylphosphanyl)benzamide by reaction with PiPr2Cl in the presence of N,N-dimethylpyridin-4-amine (DMAP) and triethylamine. NMR spectroscopy and X-ray diffraction analyses have been performed to characterize the new compound and elucidate its molecular structure in the solid state. N-(diisopropylphosphanyl)benzamide adds to the limited family of amido-substituted phosphines, RC(O)NHPR’2, which can be classified as bidentate hybrid P,O-ligands, both in their neutral and anionic forms, the latter achievable by deprotonation of the NH group. Full article
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Figure 1

5 pages, 952 KiB  
Short Note
2-((5-(5-Methyl-2-phenyl-1H-imidazol-4-yl)-1,3,4-oxadiazol-2-yl)thio)-1-phenylethan-1-one
by Bakr F. Abdel-Wahab, Ahmed F. Mabied, James C. Fettinger, Ahmed H. E. Hassan and Abdelbasset A. Farahat
Molbank 2023, 2023(2), M1666; https://doi.org/10.3390/M1666 - 09 Jun 2023
Viewed by 1006
Abstract
A promising imidazole compound was synthesized through the following route. The reaction of 5-methyl-2-phenyl-1H-imidazole-4-carbohydrazide (1) with carbon disulfide and potassium hydroxide in ethanol (80%) afforded potassium salt (2). Refluxing of (2) with phenacyl bromide ( [...] Read more.
A promising imidazole compound was synthesized through the following route. The reaction of 5-methyl-2-phenyl-1H-imidazole-4-carbohydrazide (1) with carbon disulfide and potassium hydroxide in ethanol (80%) afforded potassium salt (2). Refluxing of (2) with phenacyl bromide (3) in ethanol/water (1:1) gave 2-((5-(5-methyl-2-phenyl-1H-imidazol-4-yl)-1,3,4-oxadiazol-2-yl)thio)-1-phenylethan-1-one (4) in a 76% yield. The structure of the title heterocycle (4) was confirmed by single-crystal X-ray diffraction and nuclear magnetic resonance. Full article
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Figure 1

6 pages, 1349 KiB  
Short Note
(2Z,5Z)-5-((3-(Benzofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)-2-((4-methoxyphenyl)imino)-3-phenylthiazolidin-4-one
by Bakr F. Abdel-Wahab, Hanan A. Mohamed, Benson M. Kariuki and Gamal A. El-Hiti
Molbank 2023, 2023(2), M1665; https://doi.org/10.3390/M1665 - 09 Jun 2023
Cited by 2 | Viewed by 1013
Abstract
The reaction of a 1:1 mixture of 3-(benzofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde (1) and 2-((4-methoxyphenyl)imino)-3-phenylthiazolidin-4-one (2) in anhydrous ethanol containing piperidine as a catalyst under reflux for 4 h gave (2Z,5Z)-5-((3-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)-2-((4-methoxyphenyl)imino)-3-phenylthiazolidin-4-one (3), C34H [...] Read more.
The reaction of a 1:1 mixture of 3-(benzofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde (1) and 2-((4-methoxyphenyl)imino)-3-phenylthiazolidin-4-one (2) in anhydrous ethanol containing piperidine as a catalyst under reflux for 4 h gave (2Z,5Z)-5-((3-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)-2-((4-methoxyphenyl)imino)-3-phenylthiazolidin-4-one (3), C34H24N4O3F, in 82% yield. The structure of the newly synthesized heterocycle was confirmed via X-ray diffraction and spectral analyses. Full article
(This article belongs to the Section Organic Synthesis)
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Graphical abstract

4 pages, 567 KiB  
Communication
2-(((4-([2,2′:6′,2″-Terpyridin]-4′-yl)phenyl)imino)methyl)-6-methoxyphenol
by Lingsen Li, Jingjing Wang, Tianhao Gong, Kunming Liu and Juanhua Li
Molbank 2023, 2023(2), M1664; https://doi.org/10.3390/M1664 - 07 Jun 2023
Viewed by 812
Abstract
In this short note, we elaborate on a synthetic method for a new terpyridine Schiff base-bearing vanillin motif. The structure of the product was confirmed via 1H and 13C-NMR spectroscopy and FT-IR spectroscopy. Due to the peculiar coordination nature and optical [...] Read more.
In this short note, we elaborate on a synthetic method for a new terpyridine Schiff base-bearing vanillin motif. The structure of the product was confirmed via 1H and 13C-NMR spectroscopy and FT-IR spectroscopy. Due to the peculiar coordination nature and optical property of the synthesized compound, this work presents a promising colorimetric sensing molecular compound. Full article
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Scheme 1

5 pages, 658 KiB  
Short Note
4,5-Di-tert-butyl-1,3,6,8-tetraphenyl-4,5,8a,8b-tetrahydro-as-indacene
by Shakira I. Colon-Madera, Abby R. Jennings, Scott T. Iacono and Gary J. Balaich
Molbank 2023, 2023(2), M1663; https://doi.org/10.3390/M1663 - 07 Jun 2023
Viewed by 882
Abstract
Reaction of triplet O2 with the bridged dipotassium dicyclopentadienyl salt, ansa-[(CHBut)2(Ph2C5H2)2]K2(THF)3 1, in dry MeCN facilitated an intramolecular cyclopentadienyl ring-C to ring-C bond formation [...] Read more.
Reaction of triplet O2 with the bridged dipotassium dicyclopentadienyl salt, ansa-[(CHBut)2(Ph2C5H2)2]K2(THF)3 1, in dry MeCN facilitated an intramolecular cyclopentadienyl ring-C to ring-C bond formation and the precipitation of the crude product 4,5-di-tert-butyl-1,3,6,8-tetraphenyl-4,5,8a,8b-tetrahydro-as-indacene 2 as an off-white solid in a 73% yield (>95% pure, 1H NMR). Characterization of 2 was carried out using multinuclear NMR spectroscopy (1H and 13C), single-crystal X-ray crystallography, FTIR spectroscopy, and thermal analytical techniques (SDT, DSC). The molecular structure consisted of a rigid, C2-symmetric six-membered ring in a chair conformation with four of the ring-C atoms fused to 1,3-diphenylcyclopentadiene rings and the other two ring-C atoms substituted with trans di-axial But groups. Full article
(This article belongs to the Section Organic Synthesis)
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Figure 1

6 pages, 1393 KiB  
Short Note
2-(5,6-Diphenyl-1,2,4-Triazin-3-yl)pyridinium Dichloroiodate (I)
by M. Carla Aragoni, Vito Lippolis, Annalisa Mancini, Anna Pintus, Enrico Podda, James B. Orton, Simon J. Coles and Massimiliano Arca
Molbank 2023, 2023(2), M1662; https://doi.org/10.3390/M1662 - 07 Jun 2023
Viewed by 1067
Abstract
2-(5,6-diphenyl-1,2,4-triazin-3-yl)pyridinium dichloroiodate (I) (1) was synthesized by reacting 3-(2-pyridyl)-5,6-diphenyl-1,2,4-triazine with ICl in dichloromethane solution. The structural characterization of 1 by SC-XRD analysis was accompanied by elemental analysis, FT-IR, and FT-Raman spectroscopy measurements. Full article
(This article belongs to the Section Structure Determination)
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Figure 1

7 pages, 1991 KiB  
Short Note
Methyl 8- and 5-Nitro-1,4-Benzodioxane-2-Carboxylate
by Edoardo Armano, Alessandro Giraudo, Camillo Morano, Marco Pallavicini and Cristiano Bolchi
Molbank 2023, 2023(2), M1661; https://doi.org/10.3390/M1661 - 06 Jun 2023
Viewed by 814
Abstract
2-Substituted 1,4-benzodioxanes bearing one or more substituents at benzene are important templates in the design and synthesis of a large variety of biologically active compounds. One of the most straightforward synthetic strategies to prepare them in racemic form and with a 2-substituent susceptible [...] Read more.
2-Substituted 1,4-benzodioxanes bearing one or more substituents at benzene are important templates in the design and synthesis of a large variety of biologically active compounds. One of the most straightforward synthetic strategies to prepare them in racemic form and with a 2-substituent susceptible to further synthetically useful conversions is the condensation of commercially available methyl 2,3-dibromopropionate with already suitably functionalized catechol. Here, we obtain methyl 8- and 5-nitro-1,4-benzodioxane-2-carboxylate by reaction of methyl 2,3-dibromopropionate with 3-nitrocatechol. After separation, the two positional isomers could be unequivocally identified by HMBC NMR analysis. Full article
(This article belongs to the Section Organic Synthesis)
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Figure 1

7 pages, 1251 KiB  
Short Note
[4,6-Di-tert-butyl-N-(2,6-Dimethylphenyl)-o-Amidophenolato][4,6-Di-tert-butyl-N-(2,6-Dimethylphenyl)-o-Iminobenzosemiquinolato](2,2′-Bipyridyl)Indium(III)
by Irina V. Ershova, Anton V. Cherkasov and Alexandr V. Piskunov
Molbank 2023, 2023(2), M1660; https://doi.org/10.3390/M1660 - 06 Jun 2023
Viewed by 858
Abstract
A six-coordinated indium(III) complex (APMe)(imSQMe)In(bipy) (1), bearing two types of redox-active ligands—mono- (imSQMe) and dianion (APMe) of 4,6-di-tert-butyl-N-(2,6-dimethylphenyl)-o-iminobenzoquinone and 2,2′-bipyridyl—was synthesized and characterized in detail. The intense, [...] Read more.
A six-coordinated indium(III) complex (APMe)(imSQMe)In(bipy) (1), bearing two types of redox-active ligands—mono- (imSQMe) and dianion (APMe) of 4,6-di-tert-butyl-N-(2,6-dimethylphenyl)-o-iminobenzoquinone and 2,2′-bipyridyl—was synthesized and characterized in detail. The intense, well-resolved ESR spectrum of 1 in dichloromethane solution clearly indicates the spin density delocalization between both AP and imSQ ligands. The UV-vis spectrum of 1 possesses an absorption band in the NIR region. The molecular structure of compound 1 was established by single-crystal X-ray diffraction analysis. Full article
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Figure 1

4 pages, 614 KiB  
Communication
Unexpected C–O Bond Cleavage by a Copper–Phosphido Compound
by Steven G. Dannenberg and Rory Waterman
Molbank 2023, 2023(2), M1659; https://doi.org/10.3390/M1659 - 05 Jun 2023
Viewed by 872
Abstract
Copper methoxide compound IPrCuOMe was unexpectedly formed in a reaction of IPrCuPPh2 with methyl acrylate. The alkoxide product was identified from the reaction mixture spectroscopically and structurally characterized. This C–O bond cleavage reaction likely depends on nucleophilicity of the Cu–P bond of [...] Read more.
Copper methoxide compound IPrCuOMe was unexpectedly formed in a reaction of IPrCuPPh2 with methyl acrylate. The alkoxide product was identified from the reaction mixture spectroscopically and structurally characterized. This C–O bond cleavage reaction likely depends on nucleophilicity of the Cu–P bond of IPrCuPPh2. Full article
(This article belongs to the Section Structure Determination)
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Graphical abstract

8 pages, 5565 KiB  
Short Note
Bis(3-aminobenzenesulfonato-N)-diaqua-bis(N,N’-dimethylformamide-O)-copper(II)
by Susanta Hazra and Anirban Karmakar
Molbank 2023, 2023(2), M1658; https://doi.org/10.3390/M1658 - 04 Jun 2023
Cited by 1 | Viewed by 958
Abstract
Reaction of 3-aminobenzenesulfonic acid (HL1) with Cu(NO3)2·2.5H2O in H2O/DMF leads to the formation of the new bis(3-aminobenzenesulfonato-κN)-diaqua-bis(dimethylformamide-κO)-copper(II) complex [Cu(L1)2(DMF)2(H2O)2] (1) (HL1 [...] Read more.
Reaction of 3-aminobenzenesulfonic acid (HL1) with Cu(NO3)2·2.5H2O in H2O/DMF leads to the formation of the new bis(3-aminobenzenesulfonato-κN)-diaqua-bis(dimethylformamide-κO)-copper(II) complex [Cu(L1)2(DMF)2(H2O)2] (1) (HL1 = 3-aminobenzenesulfonic acid and DMF = N,N-dimethylformamide). Single crystal X-ray analysis reveals that the hexacoordinated copper(II) center adopts a distorted octahedral geometry with trans-oriented two 3-aminobenzenesulfonate ligands (L1−), two water and two dimethylformamide (DMF) molecules. Comparison of its crystal structure with that of the known bis(4-aminobenzenesulfonato-κN)diaquabis(dimethylformamide-κO)-copper(II) complex [Cu(L2)2(DMF)2(H2O)2] (2) (HL2 = 4-aminobenzenesulfonic acid) discloses that 1 and 2 are the isomers with an identical empirical formula (C18H30CuN4O10S2) and equal numbers of same coordinated solvents (DMF and water). H-bonded supramolecular structures and their corresponding topological analyses revealed a 2D with 6-connected hxl/Shubnikov plane net (3,6) for 1 and a 3D with 8-connected bcu; 8/4/c1; sqc3 net for 2, which are completely different. Full article
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Figure 1

5 pages, 1698 KiB  
Short Note
(E)-N’-(1-(Benzofuran-2-yl)ethylidene)-1-(4-Methoxyphenyl)-5-Methyl-1H-1,2,3-Triazole-4-Carbohydrazide
by Bakr F. Abdel-Wahab, Mohamed S. Bekheit, Benson M. Kariuki and Gamal A. El-Hiti
Molbank 2023, 2023(2), M1657; https://doi.org/10.3390/M1657 - 03 Jun 2023
Cited by 3 | Viewed by 1149
Abstract
The reaction of equimolar equivalents of 1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide (1) and 2-acetylbenzofuran (2) in anhydrous ethanol containing a catalytic amount of concentrated hydrochloric acid under reflux for 2 h gave (E)-N’-(1-(benzofuran-2-yl)ethylidene)-1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide (3 [...] Read more.
The reaction of equimolar equivalents of 1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide (1) and 2-acetylbenzofuran (2) in anhydrous ethanol containing a catalytic amount of concentrated hydrochloric acid under reflux for 2 h gave (E)-N’-(1-(benzofuran-2-yl)ethylidene)-1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide (3) in 86% yield. The structure of the title heterocycle 3 was confirmed using nuclear magnetic resonance and X-ray diffraction. Full article
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Graphical abstract

5 pages, 619 KiB  
Short Note
(E)-6-Hydroxy-2-oxo-2H-chromen-7-yl 3-(4-hydroxy-3-methoxyphenyl)acrylate
by Yang-Heon Song
Molbank 2023, 2023(2), M1656; https://doi.org/10.3390/M1656 - 02 Jun 2023
Viewed by 1028
Abstract
A hybrid compound 5: (E)-6-hydroxy-2-oxo-2H-chromen-7-yl 3-(4-hydroxy-3-methoxyphenyl)acrylate composed of (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (ferulic acid) 1 and 6,7-hydroxycoumarin (esculetin) 3 was prepared in a 61% yield by the esterification reaction of protected ferulic acid 2a with esculetin 3 in [...] Read more.
A hybrid compound 5: (E)-6-hydroxy-2-oxo-2H-chromen-7-yl 3-(4-hydroxy-3-methoxyphenyl)acrylate composed of (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (ferulic acid) 1 and 6,7-hydroxycoumarin (esculetin) 3 was prepared in a 61% yield by the esterification reaction of protected ferulic acid 2a with esculetin 3 in the presence of triethylamine in dichloromethane for 3 h, followed by deprotection using 3M HCl. The structure of compound 5 was confirmed by 1H, 13C NMR spectroscopy, mass-spectrometry and elemental analysis. Full article
(This article belongs to the Section Organic Synthesis)
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Graphical abstract

8 pages, 1373 KiB  
Communication
Synthesis of Catena-bis(μ-bromo)-(O-methyl-N-phenylthiocarbamate)-dicopper(I) and Its Reactivity towards PAr3 (Ar = Ph, p-Tol)
by Wafa Arar, Lydie Viau, Isabelle Jourdain, Michael Knorr, Carsten Strohmann, Rebecca Scheel and Azaiez Ben Akacha
Molbank 2023, 2023(2), M1655; https://doi.org/10.3390/M1655 - 31 May 2023
Cited by 1 | Viewed by 1083
Abstract
In order to investigate the coordination chemistry of O-alkyl N-aryl thiocarbamate ligands toward coinage metals, CuBr was reacted with one equivalent of MeOC(=S)N(H)Ph L in MeCN solution to afford the 1D-polymeric title compound [{Cu(μ2-Br)2Cu}{μ2-MeOC(=S)N(H)Ph} [...] Read more.
In order to investigate the coordination chemistry of O-alkyl N-aryl thiocarbamate ligands toward coinage metals, CuBr was reacted with one equivalent of MeOC(=S)N(H)Ph L in MeCN solution to afford the 1D-polymeric title compound [{Cu(μ2-Br)2Cu}{μ2-MeOC(=S)N(H)Ph}2]n CP1. Compound 1 was characterized by IR spectroscopy and an elemental analysis. The formation of a polymeric 1D ribbon built upon μ2-bridging bromido and thione ligands via the C=S bond was ascertained by a single-crystal X-ray diffraction study performed at 100 K. In the presence of PAr3 (Ar = Ph, p-Tol), the polymer chain was broken to yield the mononuclear complexes [(Ar3P)2Cu{MeOC(=S)N(H)Ph}Br] C1 and C2. Full article
(This article belongs to the Section Organic Synthesis)
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Figure 1

9 pages, 3343 KiB  
Communication
Synthesis and Spectroscopic Characterization of Furan-2-Carbaldehyde-d
by Jonas Jaster, Elias Dressler, Robert Geitner and Gregor Alexander Groß
Molbank 2023, 2023(2), M1654; https://doi.org/10.3390/M1654 - 31 May 2023
Viewed by 1825
Abstract
Here, we present a protocol for the one-step synthesis of the title compound in quantitative yield using adapted Vilsmeier conditions. The product was characterized by 1H-,2H-,13C-NMR-, as well as IR and Raman spectroscopy. Spectral data are given in detail. Full article
(This article belongs to the Section Organic Synthesis)
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Figure 1

9 pages, 1534 KiB  
Communication
Phosphine–Stibine and Phosphine–Stiborane peri-Substituted Donor–Acceptor Complexes
by Jan U. Bergsch, Alexandra M. Z. Slawin, Petr Kilian and Brian A. Chalmers
Molbank 2023, 2023(2), M1653; https://doi.org/10.3390/M1653 - 30 May 2023
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Abstract
Two novel Sb(III) and Sb(V) peri-substituted acenaphthene phosphorus−antimony compounds were prepared. The Sb(III) compound, 1, was prepared via reacting the organolithium precursor with dichloro(p-tolyl)Stibine, and 2 was prepared by the chlorination of 1. Both 1 and 2 were [...] Read more.
Two novel Sb(III) and Sb(V) peri-substituted acenaphthene phosphorus−antimony compounds were prepared. The Sb(III) compound, 1, was prepared via reacting the organolithium precursor with dichloro(p-tolyl)Stibine, and 2 was prepared by the chlorination of 1. Both 1 and 2 were characterized by multinuclear (1H, 13C and 31P) NMR spectroscopy, and their molecular structures resolved by single-crystal X-ray diffraction. Both compounds show a dative P−Sb interaction with the antimony being the acceptor group in both cases owing to its Lewis acidity. Full article
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6 pages, 572 KiB  
Short Note
Isoetin 2′-O-α-l-arabinopyranoside-5′-O-β-d-glucopyranoside
by Mayra Galarza Pérez, Fabian Fell, Dimitrina Zheleva-Dimitrova and Christian Zidorn
Molbank 2023, 2023(2), M1652; https://doi.org/10.3390/M1652 - 26 May 2023
Viewed by 1020
Abstract
Isoetin derivatives are a rare class of flavonoids with a rather erratic occurrence across the plant kingdom. The Cichorieae tribe of the Asteraceae family has proven to be a rich source and a centre of chemical diversity of this class of compounds. Here, [...] Read more.
Isoetin derivatives are a rare class of flavonoids with a rather erratic occurrence across the plant kingdom. The Cichorieae tribe of the Asteraceae family has proven to be a rich source and a centre of chemical diversity of this class of compounds. Here, we describe the chromatographic isolation and mainly NMR-based structure elucidation of a previously undescribed isoetin derivative from Leontodon hispidus L. (Asteraceae, Cichorieae). The chemophenetic relevance is discussed briefly. Full article
(This article belongs to the Section Natural Products)
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6 pages, 646 KiB  
Short Note
1-(((6-(Methoxycarbonyl)-5-oxononan-4-yl)oxy)carbonyl)cyclopropane-1-carboxylic Acid
by Evgenii S. Gorlov, Diana V. Shuingalieva, Alexey I. Ilovaisky, Vera A. Vil’ and Alexander O. Terent’ev
Molbank 2023, 2023(2), M1651; https://doi.org/10.3390/M1651 - 24 May 2023
Viewed by 1037
Abstract
Here, we first report the 2′-acyloxy-1,3-dicarbonyl compound construction in a three-component oxidative reaction of alkyl ketene dimer with cyclic diacyl peroxide and trimethyl orthoformate. The discovered synthesis allows us to form 2′-functionalized 1,3-dicarbonyl compounds instead of the common 2-functionalized moiety. The reaction between [...] Read more.
Here, we first report the 2′-acyloxy-1,3-dicarbonyl compound construction in a three-component oxidative reaction of alkyl ketene dimer with cyclic diacyl peroxide and trimethyl orthoformate. The discovered synthesis allows us to form 2′-functionalized 1,3-dicarbonyl compounds instead of the common 2-functionalized moiety. The reaction between 4-butylidene-3-propyloxetan-2-one and cyclopropyl malonoyl peroxide proceeds in the presence of trifluoroacetic acid and trimethyl orthoformate at 120 °C for 1 h. The synthesized compound was characterized by NMR spectroscopy, mass spectrometry, and IR spectroscopy. Full article
(This article belongs to the Section Organic Synthesis)
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6 pages, 966 KiB  
Short Note
(R)-(+)-3,5-Dinitro-N-(1-phenylethyl)benzothioamide
by Matthew G. Donahue and Emily Crull
Molbank 2023, 2023(2), M1650; https://doi.org/10.3390/M1650 - 20 May 2023
Viewed by 1005
Abstract
(R)-(+)-3,5-dinitro-N-(1-phenylethyl)benzothioamide 1 is a potential chiral solvating agent (CSA) for the spectral resolution of enantiomers via 1H NMR spectroscopy. The single enantiomer of 1 was synthesized from commercially available (R)-(+)-a-methylbenzylamine 2 in two steps with 85% yield. Full article
(This article belongs to the Section Organic Synthesis)
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4 pages, 321 KiB  
Short Note
5,6-Dihydro-[1,2,5]oxadiazolo[3,4-d]pyridazine-4,7-dione
by Timofey N. Chmovzh, Karim S. Gaisin and Oleg A. Rakitin
Molbank 2023, 2023(2), M1649; https://doi.org/10.3390/M1649 - 18 May 2023
Viewed by 1109
Abstract
1,2,5-Chalcogenadiazoles fused with electron-withdrawing heterocycles have been actively investigated for the preparation of organic photovoltaic materials. [1,2,5]Oxadiazolo[3,4-d]pyridazines are much less studied than other chalcogenadiazolopyridazines due to their low availability. In this communication, we report our study showing that 5,6-dihydro-[1,2,5]oxadiazolo[3,4-d]pyridazine-4,7-dione, a key precursor for [...] Read more.
1,2,5-Chalcogenadiazoles fused with electron-withdrawing heterocycles have been actively investigated for the preparation of organic photovoltaic materials. [1,2,5]Oxadiazolo[3,4-d]pyridazines are much less studied than other chalcogenadiazolopyridazines due to their low availability. In this communication, we report our study showing that 5,6-dihydro-[1,2,5]oxadiazolo[3,4-d]pyridazine-4,7-dione, a key precursor for the synthesis of 4,7-dihalo-[1,2,5]oxadiazolo[3,4-d]pyridazines, is formed via the cyclization of 1,2,5-oxadiazole-3,4-dicarbohydrazide in hydrochloric acid. The structure of the newly synthesized compound was established by means of elemental analysis; high-resolution mass spectrometry; 1H and 13C NMR; IR spectroscopy, and mass spectrometry. Full article
(This article belongs to the Collection Heterocycle Reactions)
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6 pages, 1690 KiB  
Short Note
5-(4-Chlorophenyl)-N,1-di-o-tolyl-1H-imidazole-2-amine
by Francesco Messa, Paride Papadia, Serena Perrone and Antonio Salomone
Molbank 2023, 2023(2), M1648; https://doi.org/10.3390/M1648 - 17 May 2023
Viewed by 1102
Abstract
A new 2-amino imidazole derivative, 5-(4-chlorophenyl)-N,1-di-o-tolyl-1H-imidazole-2-amine (3), has been synthesized using a green approach. The reaction was conducted in a ChCl (cholinium chloride)/urea eutectic mixture, which is a nature-inspired and environmentally friendly reaction medium. The proposed reaction mechanism involves [...] Read more.
A new 2-amino imidazole derivative, 5-(4-chlorophenyl)-N,1-di-o-tolyl-1H-imidazole-2-amine (3), has been synthesized using a green approach. The reaction was conducted in a ChCl (cholinium chloride)/urea eutectic mixture, which is a nature-inspired and environmentally friendly reaction medium. The proposed reaction mechanism involves the preliminary regioselective alkylation of the Nsp2 of guanidine (2), followed by an intramolecular condensation between the carbonyl moiety and the secondary N′sp3. Finally, a tautomerization/aromatization step furnished the final product (3). Notably, 2-amino imidazole (3) could be isolated in high yield (91%), just by filtration from the DES/water mixture and subsequent crystallization; the remaining ChCl/urea could be recycled, after water removal, for four consecutive reactions without any significant drop in the (3) yield. The product has been fully characterized by 1H, 13C, 2D 1H-13C HSQC, and 2D 1H-13C HMBC NMR; FT-IR spectroscopy; and EI-MS spectrometry. Full article
(This article belongs to the Collection Heterocycle Reactions)
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11 pages, 4024 KiB  
Communication
Structural Elucidation of 2-(6-(Diethylamino)benzofuran-2-yl)-3-hydroxy-4H-chromen-4-one and Labelling of Mycobacterium aurum Cells
by Adrian Richter, Richard Goddard, Fabienne Siersleben, Lea Mann and Rüdiger W. Seidel
Molbank 2023, 2023(2), M1647; https://doi.org/10.3390/M1647 - 16 May 2023
Cited by 1 | Viewed by 1338
Abstract
Trehalose conjugates of 3-hydroxychromone (3HC) dyes have previously been utilized as fluorescence labels to detect metabolically active mycobacteria with a view to facilitating point-of-care detection of mycobacterial pathogens, especially Mycobacterium tuberculosis. We subjected the 3HC dye 2-(6-(diethylamino)benzofuran-2-yl)-3-hydroxy-4H-chromen-4-one (3HC-2) [...] Read more.
Trehalose conjugates of 3-hydroxychromone (3HC) dyes have previously been utilized as fluorescence labels to detect metabolically active mycobacteria with a view to facilitating point-of-care detection of mycobacterial pathogens, especially Mycobacterium tuberculosis. We subjected the 3HC dye 2-(6-(diethylamino)benzofuran-2-yl)-3-hydroxy-4H-chromen-4-one (3HC-2) to a combined X-ray crystallography and density functional theory (DFT) study, and conducted preliminary fluorescence labelling experiments with the model organism Mycobacterium aurum. In the crystal, 3HC-2 exhibits an s-cis conformation of the chromone and the benzofuran moieties about the central C–C bond. According to DFT calculations, the s-cis conformer is about 1.8 kcal mol−1 lower in energy than the s-trans conformer. The solid-state supramolecular structure features hydrogen-bonded dimers and π…π stacking. Fluorescence microscopy revealed fluorescence of M. aurum cells treated with the dye trehalose conjugate 3HC-2-Tre in the GFP channel. It was concluded that s-cis is the preferred conformation of 3HC-2 and that the generally considered non-pathogenic M. aurum can be labelled with the fluorescence probe 3HC-2-Tre for convenient in vitro drug screening of new antimycobacterial agents. Full article
(This article belongs to the Section Structure Determination)
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5 pages, 923 KiB  
Short Note
1-(3-Isoselenocyanatopropyl)adamantane
by Dmitry Pitushkin, Vladimir Burmistrov and Gennady Butov
Molbank 2023, 2023(2), M1646; https://doi.org/10.3390/M1646 - 15 May 2023
Viewed by 954
Abstract
The title compound, 1-(3-isoselenocyanatopropyl)adamantane, was synthesized for the first time from 3-(adamantan-1-yl)propan-1-amine by the two-stage reaction with 1-(3-isocyanopropyl)adamantane as intermediate. The product was characterized by NMR, GC-MS, and elemental analysis. Full article
(This article belongs to the Section Organic Synthesis)
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4 pages, 1139 KiB  
Communication
Synthesis and Structure of N-(1-(Bromomethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl)benzenesulfonamide
by Ivan A. Garagan, Mikhail Yu. Moskalik, Irina V. Sterkhova and Anton S. Ganin
Molbank 2023, 2023(2), M1645; https://doi.org/10.3390/M1645 - 15 May 2023
Viewed by 1061
Abstract
A new bicyclic sulfonamide derivative, N-(1-(bromomethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl)benzenesulfonamide, was synthesized in the reaction of benzenesulfonamide and camphene in the presence of N-bromosuccinimide in acetonitrile. The proposed mechanism of investigated reaction involves the Wagner–Meerwein rearrangement stage. 3-(Bromomethylene)-2,2-dimethylbicyclo[2.2.1]heptane was isolated as a minor product. The products were [...] Read more.
A new bicyclic sulfonamide derivative, N-(1-(bromomethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl)benzenesulfonamide, was synthesized in the reaction of benzenesulfonamide and camphene in the presence of N-bromosuccinimide in acetonitrile. The proposed mechanism of investigated reaction involves the Wagner–Meerwein rearrangement stage. 3-(Bromomethylene)-2,2-dimethylbicyclo[2.2.1]heptane was isolated as a minor product. The products were characterized by IR, NMR spectroscopy, X-ray diffraction analysis, HRMS and elemental analysis data. Full article
(This article belongs to the Section Organic Synthesis)
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4 pages, 1645 KiB  
Short Note
4,4′-(((Perfluoropropane-2,2-diyl)bis(4,1-phenylene))bis(oxy))-bis(2,3,5,6-tetrafluoropyridine)
by Katelyn D. Thompson, Nathan J. Weeks, Gary J. Balaich and Scott T. Iacono
Molbank 2023, 2023(2), M1644; https://doi.org/10.3390/M1644 - 15 May 2023
Viewed by 1520
Abstract
The title compound was synthesized in near-quantitative yield using nucleophilic aromatic substitution of 4,4′-(hexafluoroisopropylidene)diphenol (BPAF) with perfluoropyridine (PFP). The purity and structure were determined by NMR (1H, 13C, 19F), GC–EIMS, and single-crystal X-ray crystallography. Full article
(This article belongs to the Section Organic Synthesis)
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