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Molbank
Volume 2022
Issue 4
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Molbank, Volume 2022, Issue 4 (December 2022) – 82 articles

Cover Story (view full-size image): Despite being known for 65 years, tert-butyl carbazate has not had its solid state structure investigated until now. Quite surprisingly, the X-ray crystal structure shows four independent molecules in the unit cell. These are arranged in rectangular groups that form a repeat unit packed in the crystal in alternating pairs with an orthogonal orientation, and are further joined into infinite chains by hydrogen bonding. View this paper
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4 pages, 1209 KiB  
Short Note
Aminophenyl-Aza-BODIPY
by Dmitry Merkushev, Tatyana Kokurina and Yuriy Marfin
Molbank 2022, 2022(4), M1530; https://doi.org/10.3390/M1530 - 19 Dec 2022
Cited by 2 | Viewed by 1174
Abstract
aza-BODIPYs are a promising class of IR fluorescent dyes. The introduction of specific substituents could allow these compounds to act as fluorescent sensors. In this work, a new aminophenyl-substituted aza-BODIPY was synthesized for future application as a near-IR pH probe. Full article
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Figure 1

5 pages, 382 KiB  
Communication
Ultrasound Assisted One-Pot Synthesis of Novel 3-(Aryl)-5-((4-(phenyldiazenyl)phenoxy)methyl)isoxazolines in Water
by Ayoub El Mahmoudi, Khalid Karrouchi, Hamza Tachallait and Khalid Bougrin
Molbank 2022, 2022(4), M1529; https://doi.org/10.3390/M1529 - 17 Dec 2022
Cited by 1 | Viewed by 1354
Abstract
In this work, we present an efficient one-pot method for the synthesis of three new azo-isoxazoline derivatives (4a–c) from aromatic aldehydes, hydroxylamine hydrochloride and 4-(allyloxy)azobenzene. Thus, the azo-isoxazoline derivatives (4a–c) were synthesized via 1,3-dipolar cycloaddition [...] Read more.
In this work, we present an efficient one-pot method for the synthesis of three new azo-isoxazoline derivatives (4a–c) from aromatic aldehydes, hydroxylamine hydrochloride and 4-(allyloxy)azobenzene. Thus, the azo-isoxazoline derivatives (4a–c) were synthesized via 1,3-dipolar cycloaddition using sodium dichloroisocyanurate (SDIC) as an eco-friendly and inexpensive oxidizing agent under ultrasound cavitation in water as a green solvent. The desired compounds 4a–c were obtained in high to excellent yields of 75–90%. Full article
(This article belongs to the Topic Heterocyclic Carbene Catalysis)
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Scheme 1

4 pages, 642 KiB  
Short Note
(S,S)-2-(((Hydroxynaphth-1-yl)(4′-nitrophenyl)methyl)amino)-3-methylbutanoic Acid Methyl Ester
by Maria Annunziata M. Capozzi and Cosimo Cardellicchio
Molbank 2022, 2022(4), M1528; https://doi.org/10.3390/M1528 - 15 Dec 2022
Cited by 2 | Viewed by 1276 | Correction
Abstract
The solvent-free Betti reaction of 2-naphthol, 4-nitrobenzaldehyde and (S)-valine methyl ester gave the corresponding aminobenzylnaphthol of the (S,S)-2-(((hydroxynaphth-1-yl)(4′-nitrophenyl)methyl)amino)-3-methylbutanoic acid methyl ester in good yield (59%). This product was fully characterized. We observed that the racemization that occurs [...] Read more.
The solvent-free Betti reaction of 2-naphthol, 4-nitrobenzaldehyde and (S)-valine methyl ester gave the corresponding aminobenzylnaphthol of the (S,S)-2-(((hydroxynaphth-1-yl)(4′-nitrophenyl)methyl)amino)-3-methylbutanoic acid methyl ester in good yield (59%). This product was fully characterized. We observed that the racemization that occurs in some Betti reactions with (S)-valine methyl ester was absent in this reaction, and thus the predominant (S,S)-product was obtained. Full article
(This article belongs to the Section Organic Synthesis)
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Graphical abstract

5 pages, 825 KiB  
Short Note
4′-(3,5-Dimethoxy-4-propargyloxyphenyl)-2,2′:6′,2″-terpyridine
by Romain Chameroy, Clément Deboskre, Jérôme Husson, Isabelle Jourdain and Michael Knorr
Molbank 2022, 2022(4), M1527; https://doi.org/10.3390/M1527 - 14 Dec 2022
Viewed by 1143
Abstract
The preparation and characterization of a new terpyridine molecule containing an acetylenic moiety is described. Part of this molecule, unknown in the literature, is obtained from a biomass-derived synthon that is formed from the naturally occurring syringaldehyde 4-hydroxy-3,5-dimethoxybenzaldehyde. The title compound was fully [...] Read more.
The preparation and characterization of a new terpyridine molecule containing an acetylenic moiety is described. Part of this molecule, unknown in the literature, is obtained from a biomass-derived synthon that is formed from the naturally occurring syringaldehyde 4-hydroxy-3,5-dimethoxybenzaldehyde. The title compound was fully characterized by NMR spectroscopy (1H and 13C), as well as by high-resolution mass spectrometry and infrared spectroscopy. Full article
(This article belongs to the Section Organic Synthesis)
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Figure 1

4 pages, 399 KiB  
Communication
Methyl 12-Methyl-3,9-dinitro-5,6,7,12-tetrahydro-13-oxodibenzo[b.g]bicyclo[3.3.1]nonane-6-carboxylate and Related Compounds
by Dylan R. Nanney and Richard A. Bunce
Molbank 2022, 2022(4), M1526; https://doi.org/10.3390/M1526 - 12 Dec 2022
Viewed by 945
Abstract
A synthesis of the title compound and related structures is reported. The procedure involves double alkylation of a β-ketoester followed by double SNAr ring closure from the γ carbon to give a dibenzo[3.3.1]bicyclic unit. This paper appears to be the first [...] Read more.
A synthesis of the title compound and related structures is reported. The procedure involves double alkylation of a β-ketoester followed by double SNAr ring closure from the γ carbon to give a dibenzo[3.3.1]bicyclic unit. This paper appears to be the first to generate a mid-sized bicyclic target by a double SNAr process. The synthesis can be performed in one step, but yields are superior (52–62%) when a two-stage procedure is used. Full article
(This article belongs to the Section Organic Synthesis)
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Graphical abstract

3 pages, 502 KiB  
Short Note
7,7-Difluoropentaphen-6(7H)-one
by Ok Ton Dyan and Pavel A. Zaikin
Molbank 2022, 2022(4), M1525; https://doi.org/10.3390/M1525 - 12 Dec 2022
Viewed by 912
Abstract
A new fluorinated pentaphene derivative has been obtained as a potential precursor for fluorinated polycyclic aromatic hydrocarbons. In this work, 7,7-difluoropentaphen-6(7H)-one was prepared from 1,1-difluoroanthracen-2(1H)-one via the Diels–Alder reaction with o-quinodimethane generated in situ from o-bis(dibromomethyl)benzene. The [...] Read more.
A new fluorinated pentaphene derivative has been obtained as a potential precursor for fluorinated polycyclic aromatic hydrocarbons. In this work, 7,7-difluoropentaphen-6(7H)-one was prepared from 1,1-difluoroanthracen-2(1H)-one via the Diels–Alder reaction with o-quinodimethane generated in situ from o-bis(dibromomethyl)benzene. The structure of the newly synthesized compound was confirmed by 1H, 13C, 19F NMR, IR and UV/Vis spectroscopy, as well as high-resolution mass spectrometry. Full article
(This article belongs to the Section Organic Synthesis)
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Graphical abstract

6 pages, 1722 KiB  
Short Note
9,14-Diphenyl-9,9a,10,13,13a,14-hexahydro-9,14:10,13-dimethanobenzo[f]tetraphen-15-one
by Brian A. Chalmers, David B. Cordes, Thomas Doig, Yuanyuan Du, Tomas Lebl, Meiyue Liu, Fraser Mealyou, Jasmine Rainer, Siobhan R. Smith, Ryan Walker and Iain A. Smellie
Molbank 2022, 2022(4), M1524; https://doi.org/10.3390/M1524 - 10 Dec 2022
Viewed by 1392
Abstract
X-ray crystallography has been used to characterise the title compound for the first time, 1H NMR, 13C NMR and IR spectroscopic data has also been updated from earlier reports. Full article
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Graphical abstract

5 pages, 1030 KiB  
Short Note
1,3,3,3′,3′-Pentaisopropyl-1,3,3′,6,6′,7,7′-heptahydro-1λ5-1,1′-spirobi[acenaphtho 5,6-cd][1,2,6]oxadiphosphinine]-3,3′-diium Triiodide
by Daniel Picthall, Matthew James Ray, Alexandra Martha Zoya Slawin and Petr Kilian
Molbank 2022, 2022(4), M1523; https://doi.org/10.3390/M1523 - 08 Dec 2022
Viewed by 937
Abstract
Reaction of bis(peri-substituted) triphosphine iPrP(AcenapPiPr2)2 (Acenap = acenaphthene-5,6-diyl) with iodine, followed by hydrolysis, afforded ionic species with [iPrP(AcenapP(O)iPr2)2] dication, containing P-O-P-O-P motif, balanced by triiodide anions. The [...] Read more.
Reaction of bis(peri-substituted) triphosphine iPrP(AcenapPiPr2)2 (Acenap = acenaphthene-5,6-diyl) with iodine, followed by hydrolysis, afforded ionic species with [iPrP(AcenapP(O)iPr2)2] dication, containing P-O-P-O-P motif, balanced by triiodide anions. The new species were fully characterised, including single crystal X-ray diffraction. The formation of the unusual double-bridged motif is likely a result of crowding in the peri-region. Full article
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Graphical abstract

4 pages, 686 KiB  
Short Note
(S,S)-1-(Phenyl((1′-4-nitrophenyl-ethyl)amino)methyl)-2-naphthol
by Maria Annunziata M. Capozzi and Cosimo Cardellicchio
Molbank 2022, 2022(4), M1522; https://doi.org/10.3390/M1522 - 08 Dec 2022
Cited by 3 | Viewed by 984
Abstract
The Betti reaction of 2-naphthol, benzaldehyde and (S)-1-(4-nitrophenyl)ethylamine without any solvent gave the corresponding aminobenzylnaphthol, that is the (S,S)-1-(phenyl((1′-4-nitrophenyl-ethyl)amino)methyl)-2-naphthol, in good yield (56%). The absolute configuration of the title compound was attributed by NMR analysis, a procedure [...] Read more.
The Betti reaction of 2-naphthol, benzaldehyde and (S)-1-(4-nitrophenyl)ethylamine without any solvent gave the corresponding aminobenzylnaphthol, that is the (S,S)-1-(phenyl((1′-4-nitrophenyl-ethyl)amino)methyl)-2-naphthol, in good yield (56%). The absolute configuration of the title compound was attributed by NMR analysis, a procedure that is reliable if compared with the data obtained by X-ray diffraction experiments. Full article
(This article belongs to the Section Organic Synthesis)
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Figure 1

8 pages, 788 KiB  
Short Note
(3-Methylene-2,3-dihydronaphtho[2,3-b][1,4]dioxin-2-yl)methanol
by Lorenzo Suigo, Giulia Lodigiani, Valentina Straniero and Ermanno Valoti
Molbank 2022, 2022(4), M1521; https://doi.org/10.3390/M1521 - 06 Dec 2022
Cited by 1 | Viewed by 1421
Abstract
(3-Methylene-2,3-dihydronaphtho[2,3-b][1,4]dioxin-2-yl)methanol was unexpectedly achieved as the main reaction product while applying a standard Johnson–Corey–Chaykovsky procedure to the 2,3-dihydronaphtho[2,3-b][1,4]dioxine-2-carbaldehyde, aiming at obtaining the corresponding epoxide. The structure of the recovered compound was confirmed through NMR and HRMS, the melting point [...] Read more.
(3-Methylene-2,3-dihydronaphtho[2,3-b][1,4]dioxin-2-yl)methanol was unexpectedly achieved as the main reaction product while applying a standard Johnson–Corey–Chaykovsky procedure to the 2,3-dihydronaphtho[2,3-b][1,4]dioxine-2-carbaldehyde, aiming at obtaining the corresponding epoxide. The structure of the recovered compound was confirmed through NMR and HRMS, the melting point was measured by DSC, and the organic purity was assessed using HPLC. We hypothesized the possible mechanism for the obtainment of this side product, which should involve the opening of the dioxane ring soon after the nucleophilic attack of the ylide to the carbonyl function. The consequent transfer of the negative charge allows the achievement of the phenolate function. The tautomer further rearranges, forming the unstable oxirane, which opening is favored by the acidic phenolic function, thus closing into the more stable six-membered ring compound. We confirmed the hypothesized reaction mechanism by applying the same reaction conditions while starting from the corresponding methyl ketone. This undesired compound, easily and quantitatively obtained by standard Johnson–Corey–Chaykovsky conditions, could pave the way to a new methodology for the obtainment of 2,3-disubstituted 1,4-naphthodioxanes, further derivatizable. Full article
(This article belongs to the Collection Molecules from Side Reactions)
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Figure 1

5 pages, 815 KiB  
Short Note
1-(4-Chlorophenyl)-2-methyl-2-phenyl-5-(thiophen-2-yl)-1,2-dihydro-3H-pyrrol-3-one
by Pavel A. Volkov, Kseniya O. Khrapova, Anton A. Telezhkin, Ivan A. Bidusenko, Alexander I. Albanov and Boris A. Trofimov
Molbank 2022, 2022(4), M1520; https://doi.org/10.3390/M1520 - 06 Dec 2022
Viewed by 1165
Abstract
1-(4-Chlorophenyl)-2-methyl-2-phenyl-5-(thiophen-2-yl)-1,2-dihydro-3H-pyrrol-3-one, was synthesized for the first time in 75% yield by the base-catalyzed intramolecular cyclization of 4-((4-chlorophenyl)amino)-4-phenyl-1-(thiophen-2-yl)pent-2-yn-1-one. The starting aminoacetylenic ketone was prepared by cross-coupling of available propargylamines with acyl chlorides in the presence of the PdCl2/CuI/Ph3P catalytic system. Full article
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Figure 1

6 pages, 1225 KiB  
Short Note
4-Methoxyphenethyl (E)-3-(o-tolyl)acrylate
by Mardi Santoso, Egar Pamela, Ersya Yanu Ramadhani, Yan Alamanda Ilfahmi, Nur Pasca Aijijiyah, Adi Setyo Purnomo and Surya Rosa Putra
Molbank 2022, 2022(4), M1519; https://doi.org/10.3390/M1519 - 05 Dec 2022
Cited by 1 | Viewed by 1440
Abstract
4-Methoxyphenethyl (E)-3-(o-tolyl)acrylate (1) was obtained in a good yield by the reaction of 2-methylcinnamic acid, 4-methoxyphenethyl alcohol, 2-methyl-6-nitrobenzoic anhydride, 4-dimethylaminopyridine, and triethylamine at room temperature for 40 min. The structure of 4-methoxyphenethyl (E)-3-(o-tolyl)acrylate [...] Read more.
4-Methoxyphenethyl (E)-3-(o-tolyl)acrylate (1) was obtained in a good yield by the reaction of 2-methylcinnamic acid, 4-methoxyphenethyl alcohol, 2-methyl-6-nitrobenzoic anhydride, 4-dimethylaminopyridine, and triethylamine at room temperature for 40 min. The structure of 4-methoxyphenethyl (E)-3-(o-tolyl)acrylate (1) was established by FTIR, NMR, and the high resolution of mass spectroscopies. 4-Methoxyphenethyl (E)-3-(o-tolyl)acrylate (1) showed higher α-glucosidase inhibition activity than standard drug acarbose. The molecular docking study exhibited that the title compound 1 had a good affinity for α-glucosidase (PDB ID: 3W37) and formed some interactions with the α-glucosidase active site residue. Full article
(This article belongs to the Section Organic Synthesis)
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Figure 1

4 pages, 639 KiB  
Short Note
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl (R)-4-methylbenzenesulfonimidate
by Arianna Tota, Michael Andresini, Marco Colella, Roberta Savina Dibenedetto, Leonardo Degennaro and Renzo Luisi
Molbank 2022, 2022(4), M1518; https://doi.org/10.3390/M1518 - 05 Dec 2022
Cited by 1 | Viewed by 1430
Abstract
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (R)-4-methylbenzenesulfonimidate was synthesized via the stereoselective NH-transfer to (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (S)-4-methylbenzenesulfinate. The reaction employed diacetoxyiodobenzene (DIB) and ammonium carbamate, and occurred in acetonitrile at room temperature. The [...] Read more.
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (R)-4-methylbenzenesulfonimidate was synthesized via the stereoselective NH-transfer to (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (S)-4-methylbenzenesulfinate. The reaction employed diacetoxyiodobenzene (DIB) and ammonium carbamate, and occurred in acetonitrile at room temperature. The imidation of sulfur proceeded with complete stereocontrol, and the reaction afforded the desired product as a single diastereoisomer and with high enantiocontrol (e.r. = 97:3) in 70% yield. The product was characterized by 1H-NMR, 13C-NMR, COSY, HSQC, IR spectroscopy, HRMS, and the enantiomeric ratio was established by HPLC analysis at the chiral stationary phase. Full article
(This article belongs to the Section Organic Synthesis)
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Graphical abstract

7 pages, 1598 KiB  
Short Note
Bis(3,4-diphenyl)(2-methythienyl)cyclopentadienyl Terbium Chloride
by Alexander A. Vinogradov, Pavel D. Komarov, Lada N. Puntus, Konstantin A. Lyssenko, Ilya E. Nifant’ev, Evgenia A. Varaksina, Ilya V. Taydakov and Dmitrii M. Roitershtein
Molbank 2022, 2022(4), M1517; https://doi.org/10.3390/M1517 - 05 Dec 2022
Viewed by 1075
Abstract
A new terbium(III) complex with a (3,4-diphenyl)(2-methylthienyl)cyclopentadienyl ligand was synthesized. Single-crystal X-ray analysis revealed a binuclear biscyclopentadienyl complex with a [TbCl2K]2 core. Luminescence properties of the terbium complex were analyzed. Full article
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Figure 1

6 pages, 1738 KiB  
Short Note
3-Phenyl-10-(2,3,4-trimethoxyphenyl)-9,10-dihydro-4H,8H-pyrano [2,3-f]chromene-4,8-dione
by Boris V. Lichitsky, Andrey N. Komogortsev and Valeriya G. Melekhina
Molbank 2022, 2022(4), M1516; https://doi.org/10.3390/M1516 - 05 Dec 2022
Viewed by 1110
Abstract
An efficient telescoped method for synthesis of 3-phenyl-10-(2,3,4-trimethoxyphenyl)-9,10-dihydro-4H,8H-pyrano[2,3-f]chromene-4,8-dione was elaborated. The presented protocol includes the one-pot multicomponent reaction of 7-hydroxy-3-phenyl-4H-chromen-4-one, 2,3,4-trimethoxybenzaldehyde and Meldrum’s acid. Advantages of this method are the application of readily available starting [...] Read more.
An efficient telescoped method for synthesis of 3-phenyl-10-(2,3,4-trimethoxyphenyl)-9,10-dihydro-4H,8H-pyrano[2,3-f]chromene-4,8-dione was elaborated. The presented protocol includes the one-pot multicomponent reaction of 7-hydroxy-3-phenyl-4H-chromen-4-one, 2,3,4-trimethoxybenzaldehyde and Meldrum’s acid. Advantages of this method are the application of readily available starting reagents, atom economy and easy procedure of preparation and purification of the target product. The structure of the synthesized polycyclic compound was proved by 1H, 13C-NMR, IR spectroscopy and high-resolution mass spectrometry with electrospray ionization (ESI-HRMS). Full article
(This article belongs to the Section Organic Synthesis)
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Figure 1

9 pages, 2138 KiB  
Short Note
5-(4-Nitrophenyl)furan-2-carboxylic Acid
by Matteo Mori, Andrea Tresoldi, Stefania Villa, Giulia Cazzaniga, Marco Bellinzoni and Fiorella Meneghetti
Molbank 2022, 2022(4), M1515; https://doi.org/10.3390/M1515 - 02 Dec 2022
Viewed by 1259
Abstract
The ever-evolving research in the field of antitubercular agents has led to the identification of several new potential drug classes. Among them, 5-phenyl-furan-2-carboxylic acids have emerged as innovative potential therapeutics, targeting iron acquisition in mycobacterial species. In our efforts to characterize the molecular [...] Read more.
The ever-evolving research in the field of antitubercular agents has led to the identification of several new potential drug classes. Among them, 5-phenyl-furan-2-carboxylic acids have emerged as innovative potential therapeutics, targeting iron acquisition in mycobacterial species. In our efforts to characterize the molecular interactions between these compounds and their protein target (MbtI from M. tuberculosis) by means of co-crystallization experiments, we unexpectedly obtained the structure of 5-(4-nitrophenyl)furan-2-carboxylic acid (1). Herein, we describe the preparation of the compound and its analysis by 1H NMR, 13C NMR, HRMS, and SC-XRD. Full article
(This article belongs to the Section Structure Determination)
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Figure 1

4 pages, 244 KiB  
Short Note
2-(2,5-Dimethoxyphenoxy)isoindoline-1,3-dione
by Stanislav A. Paveliev, Oleg O. Segida and Alexander O. Terent’ev
Molbank 2022, 2022(4), M1514; https://doi.org/10.3390/M1514 - 02 Dec 2022
Viewed by 1323
Abstract
In this work, the direct C-H functionalization reaction of 1,4-dimethoxybenzene with N-hydroxyphthalimide has been disclosed. A previously unknown product of the C-O coupling of 1,4-dimethoxybenzene and N-hydroxyphthalimide was obtained. The reaction proceeded under mild conditions, in which a commercially available manganese-based [...] Read more.
In this work, the direct C-H functionalization reaction of 1,4-dimethoxybenzene with N-hydroxyphthalimide has been disclosed. A previously unknown product of the C-O coupling of 1,4-dimethoxybenzene and N-hydroxyphthalimide was obtained. The reaction proceeded under mild conditions, in which a commercially available manganese-based oxidizing agent was used for generation of a phthalimide-N-oxyl radical. The obtained compound is a promising valuable precursor of O-aryl hydroxylamine. Full article
(This article belongs to the Section Organic Synthesis)
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Scheme 1

3 pages, 339 KiB  
Short Note
3-(3-Bromophenyl)-7-acetoxycoumarin
by Petri A. Turhanen, Liisa P. Nousiainen and Juri M. Timonen
Molbank 2022, 2022(4), M1513; https://doi.org/10.3390/M1513 - 02 Dec 2022
Viewed by 1071
Abstract
In natural product synthesis, the procurement of easily accessible starting materials is crucial. Chromenones and their subclass, coumarins, are a wide family of small, oxygen-containing aromatic heterocycles. Phenylcoumarins offer a particularly excellent starting point for a diverse chemical space of natural products, and [...] Read more.
In natural product synthesis, the procurement of easily accessible starting materials is crucial. Chromenones and their subclass, coumarins, are a wide family of small, oxygen-containing aromatic heterocycles. Phenylcoumarins offer a particularly excellent starting point for a diverse chemical space of natural products, and thus are excellent staring materials for more complex natural products. Herein, we report an efficient synthesis of an easily accessible 3-phenylcoumarin bearing two orthogonally substitutable groups, bromine, and an acetyl-protected phenylic hydroxyl group. Full article
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Scheme 1

6 pages, 1377 KiB  
Short Note
N,N′-4,5-Dimethoxy-1,2-phenylenebis(salicylideneiminato)nickel(II)
by Evgenia Smirnova, Ruslan Baichurin, Nikolai Viktorov, Dar’ya Spiridonova, Alexander Timonov and Mikhail Karushev
Molbank 2022, 2022(4), M1512; https://doi.org/10.3390/M1512 - 02 Dec 2022
Cited by 2 | Viewed by 1076
Abstract
The title compound, which is potentially interesting as a building block for electrochemically active metallopolymers, was synthesized and characterized by single-crystal X-ray diffraction, IR and NMR spectroscopies. Full article
(This article belongs to the Section Structure Determination)
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Figure 1

5 pages, 728 KiB  
Short Note
6,6′-((Ethane-1,2-diylbis(azanediyl))bis(methylene))bis(2,4-bis(2-phenylpropan-2-yl)phenolate)zirconium(IV) Dichlorido
by Joana Hipólito, Ana M. Martins and Luis G. Alves
Molbank 2022, 2022(4), M1511; https://doi.org/10.3390/M1511 - 01 Dec 2022
Cited by 1 | Viewed by 1123
Abstract
The salan zirconium complex of formula [(H2N2O2)ZrCl2] (H2N2O2H2 = HOPh’CH2NH(CH2)2NHCH2Ph’OH, where Ph’ = 2,4-(CMe2Ph)C6H2) [...] Read more.
The salan zirconium complex of formula [(H2N2O2)ZrCl2] (H2N2O2H2 = HOPh’CH2NH(CH2)2NHCH2Ph’OH, where Ph’ = 2,4-(CMe2Ph)C6H2) was synthesized and fully characterized by NMR and single-crystal X-ray diffraction. The solid-state molecular structure of [(H2N2O2)ZrCl2] shows distorted octahedral geometry around the zirconium center with the salan ligand adopting a β-Λ-cis conformation. Full article
(This article belongs to the Section Structure Determination)
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Figure 1

6 pages, 1723 KiB  
Short Note
2-Furanylmethyl N-(2-propenyl)carbamate
by Noah C. Baker, Abby L. Mock, Ivy B. Nguyen, Savan D. Patel and David C. Forbes
Molbank 2022, 2022(4), M1510; https://doi.org/10.3390/M1510 - 01 Dec 2022
Viewed by 1193
Abstract
The overexpression of protein phosphatase 5 (PP5) has been correlated to tumor cell reproduction, making it a candidate for small molecule drug therapy. Prior work has focused on functionalized and decorated scaffolds that maximize contacts within and around the active site. The assembly [...] Read more.
The overexpression of protein phosphatase 5 (PP5) has been correlated to tumor cell reproduction, making it a candidate for small molecule drug therapy. Prior work has focused on functionalized and decorated scaffolds that maximize contacts within and around the active site. The assembly and testing of cantharidin derivatives decorated with functionalized attachments has been our focus in order to affect the optimal binding of PP5. Condensation of 2-hydroxymethylfuran with allyl isocyanate meets the metrics of the rapid installment of functionality, as part of the core scaffold. Once condensed, cycloaddition followed by hydrogenation produces the desired derivative of norcantharidin in three synthetic steps. Full article
(This article belongs to the Section Organic Synthesis)
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Graphical abstract

13 pages, 9300 KiB  
Communication
N-(p-Toluenesulfonyl)-1-(4′-acetylphenoxy)acrylimidate: Synthesis, Crystal Structure and Theoretical Studies
by Flor María Escandón-Mancilla, Alberto Cedillo-Cruz, Raúl Eduardo Gordillo-Cruz, Diego Martínez-Otero, M. V. Basavanag Unnamatla and Erick Cuevas-Yañez
Molbank 2022, 2022(4), M1509; https://doi.org/10.3390/M1509 - 28 Nov 2022
Viewed by 1295
Abstract
The formation of N-sulfonyl-1-aryloxy acrylimidate is described, for the first time, from a consecutive process, which involves a CuAAC reaction, a ketenimine formation and subsequent rearrangement between an aryl propargyl ether and a sulfonyl azide. The structure of this newly synthesized compound was [...] Read more.
The formation of N-sulfonyl-1-aryloxy acrylimidate is described, for the first time, from a consecutive process, which involves a CuAAC reaction, a ketenimine formation and subsequent rearrangement between an aryl propargyl ether and a sulfonyl azide. The structure of this newly synthesized compound was analyzed by NMR spectra and unambiguously established by X-ray analysis. In addition, theoretical calculations, which included a Hirshfeld surface, FMO, QTAIM and NCI indices analysis, corroborated the formation of π-π stacking interactions among aromatic rings, as well as C-H···O interactions between vinyl hydrogens with ketone carbonyl oxygen. Full article
(This article belongs to the Section Organic Synthesis)
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9 pages, 2069 KiB  
Communication
Diverse Hydrogen-Bonded Structural Motifs in 1,4-Diazabicyclo[2.2.2]octane N,N’-Dioxide Salts with Oxoanions
by Ksenia D. Abasheeva, Pavel A. Demakov and Vladimir P. Fedin
Molbank 2022, 2022(4), M1508; https://doi.org/10.3390/M1508 - 25 Nov 2022
Cited by 2 | Viewed by 1296
Abstract
Four new hybrid inorganic–organic salts of 1,4-diazabicyclo[2.2.2]octane N,N’-dioxide (odabco) with the formulae odabco·2HNO3 (1), odabco·HClO4 (2), odabco·H2SO4 (3) and odabco·2H2SO4 (4) were synthesized and characterized by single-crystal [...] Read more.
Four new hybrid inorganic–organic salts of 1,4-diazabicyclo[2.2.2]octane N,N’-dioxide (odabco) with the formulae odabco·2HNO3 (1), odabco·HClO4 (2), odabco·H2SO4 (3) and odabco·2H2SO4 (4) were synthesized and characterized by single-crystal x-ray diffraction (XRD), powder XRD and infrared spectroscopy. Compound 1 is based on the isolated (H2odabco)2+ fragments, representing 0D structure. 2 is based on cationic 1D {Hodabco}nn+ hydrogen-bonded chains. Compound 3 comprising a strongly coordinated sulfate anion consists of two-component hydrogen-bonded {-H2odabco-SO4−} fragments forming uncharged 1D helical chains. 4 contains both {-HSO4-}nn– and {-HSO4-H2odabco-HSO4−} hydrogen bonding motifs, resulting in a 3D polymeric network. A comparative structural analysis of both the obtained and the previously reported cognate structures was performed to rationalize the impact of the degree of odabco protonation and the anion donor ability on the structural features and dimensionalities of odabco-based hydrogen-bonded lattices. Full article
(This article belongs to the Section Structure Determination)
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5 pages, 481 KiB  
Communication
Synthesis of 6-Methyluracilpentylviologen Resorcinarene Cavitand
by Albina Y. Ziganshina, Elina E. Mansurova, Marina M. Shulaeva, Viktor V. Syakaev, Vyacheslav E. Semenov and Igor S. Antipin
Molbank 2022, 2022(4), M1507; https://doi.org/10.3390/M1507 - 25 Nov 2022
Cited by 1 | Viewed by 1154
Abstract
Resorcinarenes, as macrocyclic compounds, are widely used to recognize substrates and create supramolecular assemblies. Their bowl-like form organizes functional groups at the upper and lower rims, which has a substantial impact on the molecular recognition of various substrates. As a result, resorcinarenes make [...] Read more.
Resorcinarenes, as macrocyclic compounds, are widely used to recognize substrates and create supramolecular assemblies. Their bowl-like form organizes functional groups at the upper and lower rims, which has a substantial impact on the molecular recognition of various substrates. As a result, resorcinarenes make good drug nanocarrier candidates. This paper presents the synthesis of a new resorcinarene cavitand functionalized along the upper rim with methyluracil and viologen fragments for its potential use in drug delivery. Methyluracils and viologens are well-known receptor-targeted compounds capable of facilitating the vector transfer of drugs and increasing the effectiveness of their action on cells. The paper describes the synthesis of resorcinarene modified with methyluracil and viologen groups along with its structure determined by 1H-, 13C-NMR and IR spectroscopy. Full article
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4 pages, 780 KiB  
Short Note
Dichloro[N-[(η6-phenyl)methyl]-4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8tetrahydronaphthalen-2-yl)vinyl)benzamide](1,3,5-triaza-7-phosphatricyclo [3.3.1.13,7]decane-κP7)ruthenium
by Ilya A. Shutkov, Dmitrii M. Mazur, Nataliya E. Borisova, Elena R. Milaeva and Alexey A. Nazarov
Molbank 2022, 2022(4), M1506; https://doi.org/10.3390/M1506 - 25 Nov 2022
Viewed by 1093
Abstract
Bexarotene-tethered RuII(arene) compounds with 1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane (PTA) were prepared as an analog of RAPTA antitumor complexes in order to evaluate their in vitro antiproliferative activity against human cancer cell lines. Full article
(This article belongs to the Section Organic Synthesis)
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6 pages, 1658 KiB  
Communication
Novel Schiff Bases of C-Methylresorcinarene Derivatives
by Albina Y. Ziganshina, Olga S. Saranova, Rezeda R. Fazleeva, Vitaly V. Yanilkin and Igor S. Antipin
Molbank 2022, 2022(4), M1505; https://doi.org/10.3390/M1505 - 25 Nov 2022
Viewed by 1081
Abstract
The article presents the synthesis and properties of two new Schiff bases of resorcinarene derivatives. The Schiff bases were obtained by the reaction of formylresorcinarene with aromatic (o-aminophenol) and aliphatic (N,N-dimethyldiaminoethane) amines in chloroform. The synthesized Schiff [...] Read more.
The article presents the synthesis and properties of two new Schiff bases of resorcinarene derivatives. The Schiff bases were obtained by the reaction of formylresorcinarene with aromatic (o-aminophenol) and aliphatic (N,N-dimethyldiaminoethane) amines in chloroform. The synthesized Schiff bases exist in equilibrium of several tautomers, as evident from the IR, UV, NMR spectra and cyclic voltammetry data analysis. In DMF, methanol, and acetonitrile, the tautomeric equilibrium is shifted toward the enol-imine tautomers. Full article
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4 pages, 918 KiB  
Short Note
(E)-3-(2-(4-methylthiazol-2-yl)hydrazineylidene)chromane-2,4-dione
by Fatlinda Rahmani, Aurélien Crochet and Fabio Zobi
Molbank 2022, 2022(4), M1504; https://doi.org/10.3390/M1504 - 24 Nov 2022
Cited by 1 | Viewed by 1172
Abstract
(E)-3-(2-(4-methylthiazol-2-yl)hydrazineylidene)chromane-2,4-dione was synthesized for the first time and the compound was characterized by 1H and 13C spectroscopy, IR spectroscopy, and UV-Vis. The chemical structure and isomeric configuration of the molecule were confirmed by single-crystal X-ray diffraction. Full article
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7 pages, 729 KiB  
Short Note
2-Benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one
by Ivette Morales-Salazar, Mónica A. Rincón-Guevara, Eduardo González-Zamora and Alejandro Islas-Jácome
Molbank 2022, 2022(4), M1503; https://doi.org/10.3390/M1503 - 23 Nov 2022
Cited by 1 | Viewed by 1137
Abstract
The new polyheterocyclic compound 2-benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (1) was synthesized via a one-pot process involving an Ugi-Zhu three-component reaction coupled to a cascade aza-Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration process, using toluene as the solvent, ytterbium (III) triflate as the [...] Read more.
The new polyheterocyclic compound 2-benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (1) was synthesized via a one-pot process involving an Ugi-Zhu three-component reaction coupled to a cascade aza-Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration process, using toluene as the solvent, ytterbium (III) triflate as the Lewis acid catalyst, and microwave-dielectric heating to increase the overall yield by up to 73%, while decreasing the reaction time to less than one hour. Product 1 was fully characterized by its physicochemical properties and using spectroscopic techniques (IR, HRMS and NMR). Full article
(This article belongs to the Collection Heterocycle Reactions)
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8 pages, 1784 KiB  
Short Note
(η4-Tetraphenylcyclobutadiene)-(η5-pentaphenylcyclopentadienyl)-cobalt
by Christian Klein-Heßling and Karlheinz Sünkel
Molbank 2022, 2022(4), M1502; https://doi.org/10.3390/M1502 - 21 Nov 2022
Viewed by 1293
Abstract
A one-pot reaction starting with C5Ph5Br, n-BuLi and [CoCl(PPh3)3] followed by the addition of diphenylethyne produces the title compound with 12% yield. Spectroscopic characterization involved 1H, 13C-NMR, UV-Vis and mass spectrometry. A [...] Read more.
A one-pot reaction starting with C5Ph5Br, n-BuLi and [CoCl(PPh3)3] followed by the addition of diphenylethyne produces the title compound with 12% yield. Spectroscopic characterization involved 1H, 13C-NMR, UV-Vis and mass spectrometry. A crystal structure determination showed that the central aromatic rings are exactly parallel with the cyclobutadiene ring further apart from the metal as usual. The pentaphenyl–cyclopentadienyl ligand shows an usual paddlewheel orientation, whereas in the tetraphenyl–cyclobutadiene ligand, two of the phenyl groups are nearly coplanar with the four-membered ring. There are also numerous C–H…C(π) interactions between the phenyl groups on the same ring, as well as between rings. Full article
(This article belongs to the Section Structure Determination)
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6 pages, 1411 KiB  
Communication
N4-(2-Amino-4-fluorophenyl)-N1-(3-{2-[2-(3-{[2-(2,6-dioxo-3-piperidyl)-1,3-dioxoisoindolin-4-yl]amino}propoxy)ethoxy]ethoxy}propyl)terephthalamide
by Mohamed Abdelsalam, Matthes Zessin, Matthias Schmidt, Mike Schutkowski and Wolfgang Sippl
Molbank 2022, 2022(4), M1501; https://doi.org/10.3390/M1501 - 21 Nov 2022
Viewed by 1168
Abstract
The design of proteolysis targeting chimeras (PROTACs) has become a promising technology for modifying a protein of interest (POI) through protein degradation. Herein, we describe the synthetic pathway to develop N4-(2-amino-4-fluorophenyl)-N1-(3-{2-[2-(3-{[2-(2,6-dioxo-3-piperidyl)-1,3-dioxoisoindolin-4-yl]amino}propoxy)ethoxy]ethoxy}propyl)terephthalamide, which was designed to work as a [...] Read more.
The design of proteolysis targeting chimeras (PROTACs) has become a promising technology for modifying a protein of interest (POI) through protein degradation. Herein, we describe the synthetic pathway to develop N4-(2-amino-4-fluorophenyl)-N1-(3-{2-[2-(3-{[2-(2,6-dioxo-3-piperidyl)-1,3-dioxoisoindolin-4-yl]amino}propoxy)ethoxy]ethoxy}propyl)terephthalamide, which was designed to work as a selective degrader of histone deacetylase-3 (HDAC3). The newly synthesized compounds were characterized by 1H-NMR, 13C-NMR, IR and HRMS. The title compound was tested in vitro against human class-I HDACs isoforms and showed IC50 = 3.4 µM against HDAC3; however, it did not show degradation for the targeted HDACs. Full article
(This article belongs to the Section Organic Synthesis)
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