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Methyl 9-(2-Iminothiazol-3(2H)-yl)-9-oxononanoate
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1-[2-(1H-Pyrrole-2-carbonyl)phenyl]-3-(4-methoxyphenyl)urea
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Synthesis of 3-Bromo-4-phenylisothiazole-5-carboxylic Acid and 3-Bromoisothiazole-5-carboxylic Acid
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(µ2-η4-N-(2-Butynyl)phthalimide)(hexacarbonyl)dicobalt
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1-{(1S,2S,4R)-7,7-Dimethyl-1-[(pyrrolidin-1-yl)methyl]bicyclo [2.2.1]heptan-2-yl}-1H-benzo[d]imidazole
Journal Description
Molbank
Molbank
is a peer-reviewed, open access journal comprised of a unique collection of one-compound-per-paper short notes on synthetic compounds and natural products. Molbank has been published online quarterly since 2009 (previously published irregularly).
- Open Access— free for readers, with article processing charges (APC) paid by authors or their institutions.
- High Visibility: indexed within Scopus, ESCI (Web of Science), Reaxys, CAPlus / SciFinder, and other databases.
- Rapid Publication: manuscripts are peer-reviewed and a first decision is provided to authors approximately 13.1 days after submission; acceptance to publication is undertaken in 2.9 days (median values for papers published in this journal in the second half of 2022).
- Recognition of Reviewers: reviewers who provide timely, thorough peer-review reports receive vouchers entitling them to a discount on the APC of their next publication in any MDPI journal, in appreciation of the work done.
Latest Articles
6,6′-Di-(8″-quinoline)-2,2′-bipyridine Cobalt(II) Complex
Molbank 2023, 2023(2), M1615; https://doi.org/10.3390/M1615 (registering DOI) - 31 Mar 2023
Abstract
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This short note describes the synthesis of a novel compound, 6,6′-di-(8″-quinoline)-2,2′-bypyridine (2), that bears a bipyridyl backbone and quinoline donors. Compound 2 coordinates with a cobalt(II) ion in a tetradentate manner and affords the complex [CoII(2)(TfO)2
[...] Read more.
This short note describes the synthesis of a novel compound, 6,6′-di-(8″-quinoline)-2,2′-bypyridine (2), that bears a bipyridyl backbone and quinoline donors. Compound 2 coordinates with a cobalt(II) ion in a tetradentate manner and affords the complex [CoII(2)(TfO)2], whose molecular structure has been identified by single crystal X-ray diffraction crystallographic analysis. The coordination features of 2 were compared with those of 2,2′:6′,2″:6″,2‴-quaterpyridine (qtpy, 1), a well-studied tetradentate polypyridine ligand. Compound 2 presents a new example of tetradentate chelators for 3d metal ions.
Full article
Open AccessShort Note
tert-Butyl (E)-3-oxo-2-(3-oxoisobenzofuran-1(3H)-ylidene)butanoate
Molbank 2023, 2023(2), M1614; https://doi.org/10.3390/M1614 - 30 Mar 2023
Abstract
Non-fullerene acceptors have recently attracted much attention as components of organic solar cells. 1H-indene-1,3(2H)-dione is a key compound for the synthesis of the end-capping component of non-fullerene acceptors. In this communication, an intermediate for the synthesis of this compound,
[...] Read more.
Non-fullerene acceptors have recently attracted much attention as components of organic solar cells. 1H-indene-1,3(2H)-dione is a key compound for the synthesis of the end-capping component of non-fullerene acceptors. In this communication, an intermediate for the synthesis of this compound, tert-butyl (E)-3-oxo-2-(3-oxoisobenzofuran-1(3H)-ylidene)butanoate, was prepared by the reaction between phthalic anhydride and tert-butyl acetoacetate. Further treatment with sodium methoxide in methanol led to the formation of 1H-indene-1,3(2H)-dione in a high yield. The structure of the newly synthesized compound was established by means of elemental analysis, high-resolution mass spectrometry, 1H, 13C NMR, IR spectroscopy, mass spectrometry and X-ray analysis.
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(This article belongs to the Collection Heterocycle Reactions)
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Supplementary material:
Supplementary File 1 (PDF, 395 KiB)
Supplementary File 2 (INCHI, 859 B)
Supplementary File 3 (MOL, 3 KiB)
Supplementary File 1 (PDF, 395 KiB)
Supplementary File 2 (INCHI, 859 B)
Supplementary File 3 (MOL, 3 KiB)
Open AccessShort Note
6-Chloro-3-nitro-8-(phenylthio)-2-[(phenylthio)methyl] imidazo[1,2-a]pyridine
by
, , , , , , , , , and
Molbank 2023, 2023(2), M1613; https://doi.org/10.3390/M1613 (registering DOI) - 30 Mar 2023
Abstract
As part of our ongoing antikinetoplastid structure–activity relationship study focused on positions 2 and 8 of the 3-nitroimidazo[1,2-a]pyridine scaffold, we were able to introduce a phenylthioether moiety at both position 2 and position 8 in one step. Using a previously reported
[...] Read more.
As part of our ongoing antikinetoplastid structure–activity relationship study focused on positions 2 and 8 of the 3-nitroimidazo[1,2-a]pyridine scaffold, we were able to introduce a phenylthioether moiety at both position 2 and position 8 in one step. Using a previously reported synthetic route developed in our laboratory, we obtained 6-chloro-3-nitro-8-(phenylthio)-2-[(phenylthio)methyl]imidazo[1,2-a]pyridine in 74% yield. The in vitro cell viability of this compound was assessed on the HepG2 cell line, and its in vitro activity was evaluated against the promastigote form of L. donovani, the axenic amastigote form of L. infantum and the trypomastigote blood stream form of T. b. brucei. It showed low solubility in HepG2 culture medium (CC50 > 7.8 µM), associated with weak activity against both the promastigote form of L. donovani (EC50 = 8.8 µM), the axenic amastigote form of L. infantum (EC50 = 9.7 µM) and the trypomastigote blood stream form of T. b. brucei (EC50 = 12.8 µM).
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(This article belongs to the Section Organic Synthesis)
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Supplementary material:
Supplementary File 1 (PDF, 1319 KiB)
Supplementary File 2 (INCHI, 923 B)
Supplementary File 3 (MOL, 2 KiB)
Supplementary File 1 (PDF, 1319 KiB)
Supplementary File 2 (INCHI, 923 B)
Supplementary File 3 (MOL, 2 KiB)
Open AccessShort Note
3-Cyclohexyl-6-phenyl-1-(p-tolyl)pyrimidine-2,4(1H,3H)-dione
Molbank 2023, 2023(2), M1611; https://doi.org/10.3390/M1611 - 28 Mar 2023
Abstract
The synthesis of a novel uracil derivative, 3-cyclohexyl-6-phenyl-1-(p-tolyl)pyrimidine-2,4(1H,3H)-dione (4), is reported via a four-component reaction involving an α-chloroketone (1), an aliphatic isocyanate (2), a primary aromatic amine (3)
[...] Read more.
The synthesis of a novel uracil derivative, 3-cyclohexyl-6-phenyl-1-(p-tolyl)pyrimidine-2,4(1H,3H)-dione (4), is reported via a four-component reaction involving an α-chloroketone (1), an aliphatic isocyanate (2), a primary aromatic amine (3) and carbon monoxide. The proposed reaction mechanism involves a Pd-catalyzed carbonylation of 2-chloro-1-phenylethan-1-one (1), leading to a β-ketoacylpalladium key intermediate, and, at the same time, in situ formation of non-symmetrical urea deriving from cyclohexyl isocyanate (2) and p-toluidine (3). After a chemo-selective acylation of the non-symmetrical urea and the subsequent cyclization of the acylated intermediate, 3-cyclohexyl-6-phenyl-1-(p-tolyl)pyrimidine-2,4(1H,3H)-dione (4) is formed. Uracil derivative 4 was isolated in good yield (73%) and fully characterized by 1H, 13C, 2D 1H-13C HSQC and 2D 1H-13C HMBC NMR, FT-IR spectroscopy and GC-MS spectrometry.
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(This article belongs to the Collection Molecules from Catalytic Processes)
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Supplementary material:
Supplementary File 1 (PDF, 695 KiB)
Supplementary File 2 (INCHI, 1 KiB)
Supplementary File 3 (MOL, 4 KiB)
Supplementary File 1 (PDF, 695 KiB)
Supplementary File 2 (INCHI, 1 KiB)
Supplementary File 3 (MOL, 4 KiB)
Open AccessCommunication
Bis((5-allyl-2-(benzo[d][1,3]dioxol-5-yl)benzofuran-7-yl)oxy)methane: An Unusual Nor-Neolignan Dimer from Magnolia grandiflora L.
Molbank 2023, 2023(2), M1612; https://doi.org/10.3390/M1612 - 28 Mar 2023
Abstract
An unreported and unusual nor-neolignan dimer, namely bis((5-allyl-2-(benzo[d][1,3]dioxol-5-yl)benzofuran-7-yl)oxy)methane (1), was isolated from the bark-derived chloroform extract of Magnolia grandiflora L. Compound 1 was structurally elucidated through the detailed analysis of the spectroscopic data (one- and two-dimensional nuclear magnetic
[...] Read more.
An unreported and unusual nor-neolignan dimer, namely bis((5-allyl-2-(benzo[d][1,3]dioxol-5-yl)benzofuran-7-yl)oxy)methane (1), was isolated from the bark-derived chloroform extract of Magnolia grandiflora L. Compound 1 was structurally elucidated through the detailed analysis of the spectroscopic data (one- and two-dimensional nuclear magnetic resonance, infrared, and high-resolution mass spectrometry). The effect of compound 1 on the mycelial growth of Fusarium oxysporum was also determined, affording moderate antifungal activity.
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(This article belongs to the Section Natural Products)
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Bis(2-phenylpyridinato,-C2′,N)[4,4′-bis(4-Fluorophenyl)-6,6′-dimethyl-2,2′-bipyridine] Iridium(III) Hexafluorophosphate
Molbank 2023, 2023(2), M1610; https://doi.org/10.3390/M1610 - 24 Mar 2023
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A new bis cyclometallated Ir(III) phosphor, [Ir(ppy)2L]PF6 (ppy = 2-phenylpyridine, L = 4,4′-bis(4-fluorophenyl)-6,6′-dimethyl-2,2′-bipyridine was prepared and structurally characterized in the solid state (X-ray diffraction) and solution (1 and 2D NMR spectroscopy). The compound exhibited yellow photoluminescence (λem = 562
[...] Read more.
A new bis cyclometallated Ir(III) phosphor, [Ir(ppy)2L]PF6 (ppy = 2-phenylpyridine, L = 4,4′-bis(4-fluorophenyl)-6,6′-dimethyl-2,2′-bipyridine was prepared and structurally characterized in the solid state (X-ray diffraction) and solution (1 and 2D NMR spectroscopy). The compound exhibited yellow photoluminescence (λem = 562 nm). The quantum yield Φ was solvent-dependent (5% in acetonitrile and 19% in dichloromethane solutions, respectively).
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Figure 1
Open AccessShort Note
3-[4-(2-Phenylethyl)piperazin-1-yl]-7H-benzo[de]anthracen-7-one
Molbank 2023, 2023(1), M1607; https://doi.org/10.3390/M1607 - 23 Mar 2023
Abstract
The present work describes the synthesis of the new benzanthrone dye-3-[4-(2-phenylethyl)piperazin-1-yl]-7H-benzo[de]anthracen-7-one by bromine atom nucleophilic substitution reaction. The structure of the obtained benzanthrone derivative is characterized by NMR spectroscopy, mass spectrometry, and X-ray diffraction analysis. The photophysical properties of
[...] Read more.
The present work describes the synthesis of the new benzanthrone dye-3-[4-(2-phenylethyl)piperazin-1-yl]-7H-benzo[de]anthracen-7-one by bromine atom nucleophilic substitution reaction. The structure of the obtained benzanthrone derivative is characterized by NMR spectroscopy, mass spectrometry, and X-ray diffraction analysis. The photophysical properties of the target compound are investigated by means of UV-Vis and fluorescence spectroscopy in various organic solvents.
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(This article belongs to the Section Organic Synthesis)
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Open AccessCommunication
Photodimerization of (E)-3-(2,6-Difluorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one in the Crystalline Solid State
Molbank 2023, 2023(2), M1609; https://doi.org/10.3390/M1609 - 23 Mar 2023
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(E)-3-(2,6-difluorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one (1) was synthesized and characterized by 1H and 13C NMR, mass spectrometry, and single-crystal X-ray diffraction. Photolysis (λirr = 300 nm) of chalcone 1 in the crystalline solid state resulted in the stereospecific formation of the syn-head-to-head photodimer (β-truxinic).
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Figure 1
Open AccessShort Note
1-(2-Chlorophenyl)-6,7-dimethoxy-3-methyl-3,4-dihydroisoquinoline
Molbank 2023, 2023(2), M1608; https://doi.org/10.3390/M1608 - 23 Mar 2023
Abstract
This article concerns the synthesis and in silico evaluation of 1-(2-chlorophenyl)-6-7-dimethoxy-3-methyl-3,4-dihydrogioquinoline (DIQ). A variety of in silico simulations were applied to assess the potential biological activity and toxicity of the compound. Based on these analyses, the target molecule DIQ was chosen for the
[...] Read more.
This article concerns the synthesis and in silico evaluation of 1-(2-chlorophenyl)-6-7-dimethoxy-3-methyl-3,4-dihydrogioquinoline (DIQ). A variety of in silico simulations were applied to assess the potential biological activity and toxicity of the compound. Based on these analyses, the target molecule DIQ was chosen for the synthesis. DIQ was synthesized from starting 2-chloro-N-(1-(3,4-dimethoxyphenyl)propan-2-yl)benzamide applied in the Bischler–Napieralski reaction. The newly obtained 3,4-dihydroisoquinoline derivative was fully analyzed and characterized. Based on the in silico calculations, the target molecule was synthesized with respect to its contractile activity, which is a permanent interest of our studies. Thus, further investigation into the possible medicinal applications of this compound is warranted in the future.
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(This article belongs to the Section Organic Synthesis)
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Open AccessCommunication
Manganese(II) Bromide Coordination toward the Target Product and By-Product of the Condensation Reaction between 2-Picolylamine and Acenaphthenequinone
Molbank 2023, 2023(1), M1606; https://doi.org/10.3390/M1606 - 22 Mar 2023
Abstract
A heteroleptic binuclear manganese complex was obtained and characterized by single-crystal X-ray diffraction. Manganese ions coordinate with the target product and by-product of the condensation reaction between 2-picolylamine and acenaphthenequinone are characterized by different geometries in the resulting complex.
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(This article belongs to the Special Issue Molecules from Side Reactions II)
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[6-(Thiophen-2-yl)-2,2′-bipyridine]bis(triphenylphosphine) Copper(I) Tetrafluoroborate
Molbank 2023, 2023(1), M1605; https://doi.org/10.3390/M1605 - 16 Mar 2023
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The novel heteroleptic copper (I) complex [6-(thiophen-2-yl)-2,2′-bipyridine]bis(triphenylphosphine) copper(I) tetrafluoroborate (1), formulated as [CuL(PPh3)2]BF4, was synthesized in two steps, utilizing the diimine type ligand L = 6-(thiophen-2-yl)-2,2′-bipyridine and triphenylphosphine (PPh3). The compound was characterized both in
[...] Read more.
The novel heteroleptic copper (I) complex [6-(thiophen-2-yl)-2,2′-bipyridine]bis(triphenylphosphine) copper(I) tetrafluoroborate (1), formulated as [CuL(PPh3)2]BF4, was synthesized in two steps, utilizing the diimine type ligand L = 6-(thiophen-2-yl)-2,2′-bipyridine and triphenylphosphine (PPh3). The compound was characterized both in the solid state and in solution by employing single crystal X-ray diffraction, IR, UV, and NMR spectroscopies. The complex is an orange emitter that demonstrates a photoluminescence quantum yield of 2.6% in the solid state.
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Open AccessCommunication
Synthesis of 2-[2-(Ethoxymethoxy)phenyl]spiro[cyclopropane-1,2′-indene]-1′,3′-dione
by
, , , , , and
Molbank 2023, 2023(1), M1604; https://doi.org/10.3390/M1604 - 14 Mar 2023
Abstract
An 1,3-indanedione-derived donor–acceptor cyclopropane, bearing the ethoxymethyl-protected phenolic group at the ortho-position of the donor aryl substituent, has been synthesized using a reaction sequence involving the Knoevenagel condensation of 1,3-indanedione with the corresponding protected salicylaldehyde followed by the Corey–Chaykovsky cyclopropanation of the
[...] Read more.
An 1,3-indanedione-derived donor–acceptor cyclopropane, bearing the ethoxymethyl-protected phenolic group at the ortho-position of the donor aryl substituent, has been synthesized using a reaction sequence involving the Knoevenagel condensation of 1,3-indanedione with the corresponding protected salicylaldehyde followed by the Corey–Chaykovsky cyclopropanation of the obtained adduct with dimethylsulfoxonium methylide. The structure of the synthesized cyclopropane was unambiguously proved by single-crystal X-ray diffraction data.
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(This article belongs to the Section Organic Synthesis)
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6-[(2S,3R)-3-(2,4-Difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl]-5-fluoropyrimidine-4-carbaldehyde
Molbank 2023, 2023(1), M1603; https://doi.org/10.3390/M1603 - 12 Mar 2023
Abstract
Voriconazole (VN) is an antifungal drug indicated for the treatment of several fungal infections. Due to its side effects, some works involving late-stage functionalization of VN have been reported in the literature. Here, we disclose a new VN derivative, the 6-[(2
[...] Read more.
Voriconazole (VN) is an antifungal drug indicated for the treatment of several fungal infections. Due to its side effects, some works involving late-stage functionalization of VN have been reported in the literature. Here, we disclose a new VN derivative, the 6-[(2S,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl]-5-fluoropyrimidine-4-carbaldehyde (VN-CHO). This compound results from the photoredox-catalyzed hydroxymethylation of VN, affording a hydroxymethylated derivative (VN-CH2OH), followed by oxidation of the former CH2OH group. VN-CHO was obtained in good yield (70% yield) and its structure was unveiled by 1D (1H and 13C) and 2D (HSQC and HMBC) NMR techniques. The introduction of a formyl group in VN structure creates a very promising site for further functionalization in a molecule which originally does not have many active sites.
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(This article belongs to the Section Organic Synthesis)
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2-[2,6-Diisopropylphenyl]-4-phenyl-5H-5,9b[1′,2′]-benzonaphtho[1,2-b]pyrrol-2-ium Tetrafluoroborate
Molbank 2023, 2023(1), M1601; https://doi.org/10.3390/M1601 - 10 Mar 2023
Abstract
A novel α,β-unsaturated iminium salt (3) incorporated into a rigid dibenzobarrelene backbone was synthesized by heating N-(anthracen-9-ylmethyl)-2,6-diisopropylaniline (2) and 3-phenyl-2-propynal in THF in the presence of excess amounts of magnesium sulfate and 0.5 equivalents of an HBF4
[...] Read more.
A novel α,β-unsaturated iminium salt (3) incorporated into a rigid dibenzobarrelene backbone was synthesized by heating N-(anthracen-9-ylmethyl)-2,6-diisopropylaniline (2) and 3-phenyl-2-propynal in THF in the presence of excess amounts of magnesium sulfate and 0.5 equivalents of an HBF4-Et2O complex. The molecular structure of 3 was characterized unambiguously by NMR spectroscopy and single-crystal X-ray diffraction (SCXRD) analyses. Compound 3 exhibits yellow luminescence in CH2Cl2 (λem = 516 nm) and in the solid state (λem = 517 nm) with relatively high to moderate quantum yields (ΦF(CH2Cl2) = 0.63; ΦF(solid) = 0.34).
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(This article belongs to the Section Structure Determination)
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New 2-(2,4-Dihydroxyphenyl)benzimidazolines
Molbank 2023, 2023(1), M1602; https://doi.org/10.3390/M1602 - 10 Mar 2023
Abstract
New 2-(2,4-dihydroxyphenyl)benzimidazolines are synthesized in an easily accessible approach. The method is based on the reaction of resorcinol with in situ-formed electrophilic N-ethoxycarbonylbenzimidazolium reagents. The structure of the two newly formed products was spectrally characterized by 1D and 2D NMR, IR, and
[...] Read more.
New 2-(2,4-dihydroxyphenyl)benzimidazolines are synthesized in an easily accessible approach. The method is based on the reaction of resorcinol with in situ-formed electrophilic N-ethoxycarbonylbenzimidazolium reagents. The structure of the two newly formed products was spectrally characterized by 1D and 2D NMR, IR, and MS spectral analyses.
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(This article belongs to the Collection Heterocycle Reactions)
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(Z)-5-Benzylidene-4-phenyl-2-(p-tolyl)-4,5-dihydrooxazole
by
, , , , and
Molbank 2023, 2023(1), M1600; https://doi.org/10.3390/M1600 - 06 Mar 2023
Abstract
By strategic use of the valence difference between hard gold(III) and soft gold(I) catalysts, one-pot synthesis of (Z)-5-benzylidene-4-phenyl-2-(p-tolyl)-4,5-dihydrooxazole (15) from propargylic alcohol (9) and p-toluamide (13) was achieved via gold(III)-catalyzed propargylic substitution
[...] Read more.
By strategic use of the valence difference between hard gold(III) and soft gold(I) catalysts, one-pot synthesis of (Z)-5-benzylidene-4-phenyl-2-(p-tolyl)-4,5-dihydrooxazole (15) from propargylic alcohol (9) and p-toluamide (13) was achieved via gold(III)-catalyzed propargylic substitution followed by gold(I)-catalyzed cyclization. The structure of 15 was confirmed by X-ray crystallographic analysis.
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(This article belongs to the Topic Catalysis: Homogeneous and Heterogeneous)
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Open AccessCommunication
Synthesis, Characterization and Chemistry of Tetrakis(Propargylisocyanide) Copper(I) Complex
Molbank 2023, 2023(1), M1599; https://doi.org/10.3390/M1599 - 02 Mar 2023
Abstract
The kinetically unstable propargylisocyanide was reacted with the tetrakis(acetonitrile) copper(I) hexafluorophosphate and the formed complex was then involved in a copper-catalyzed alkyne-azide cycloaddition reaction (CuAAC). After the decomplexation of the adduct, the isocyanide was engaged in a Ugi reaction. By such a complexation,
[...] Read more.
The kinetically unstable propargylisocyanide was reacted with the tetrakis(acetonitrile) copper(I) hexafluorophosphate and the formed complex was then involved in a copper-catalyzed alkyne-azide cycloaddition reaction (CuAAC). After the decomplexation of the adduct, the isocyanide was engaged in a Ugi reaction. By such a complexation, reactions can be carried out on the CC triple bond without the constraint of the instability of the free compound or the competitive reactivity of the isocyanide group.
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(This article belongs to the Section Organic Synthesis)
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3-(5-Phenyl-2H-tetrazol-2-yl)pyridine
by
, , , , , , , , , , , and
Molbank 2023, 2023(1), M1598; https://doi.org/10.3390/M1598 - 28 Feb 2023
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3-(5-Phenyl-2H-tetrazol-2-yl)pyridine was synthesized by treating 5-phenyl-1H-tetrazole with pyridin-3-ylboronic acid under Chan–Evans–Lam coupling conditions. The structure and identity were confirmed by 1H, 13C-NMR spectroscopy, IR spectroscopy, UV–Vis spectroscopy, high-resolution mass spectrometry, and TLC. The molecular structure was studied
[...] Read more.
3-(5-Phenyl-2H-tetrazol-2-yl)pyridine was synthesized by treating 5-phenyl-1H-tetrazole with pyridin-3-ylboronic acid under Chan–Evans–Lam coupling conditions. The structure and identity were confirmed by 1H, 13C-NMR spectroscopy, IR spectroscopy, UV–Vis spectroscopy, high-resolution mass spectrometry, and TLC. The molecular structure was studied experimentally by sequential X-ray diffraction analysis and theoretically by DFT B3LYP quantum chemistry calculation.
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Open AccessCommunication
Synthesis of a Novel 9-O Berberine Derivative and Evaluation of Its Hypoglycemic Effect
by
, , , , , and
Molbank 2023, 2023(1), M1597; https://doi.org/10.3390/M1597 - 24 Feb 2023
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Berberine is a phytogenic isoquinoline alkaloid which demonstrates several pharmacological effects, including a hypoglycemic effect. Its medical use is limited by its very low bioavailability. Synthesizing new berberine derivatives might help in overcoming this problem. In this work, we report on the synthesis
[...] Read more.
Berberine is a phytogenic isoquinoline alkaloid which demonstrates several pharmacological effects, including a hypoglycemic effect. Its medical use is limited by its very low bioavailability. Synthesizing new berberine derivatives might help in overcoming this problem. In this work, we report on the synthesis and biological evaluation of a novel berberine 9-O-derivative. At an oral dose of 25 mg/kg, the compound demonstrated hypoglycemic activity in an oral glucose tolerance test performed using C57BL/6 mice.
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4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide
Molbank 2023, 2023(1), M1596; https://doi.org/10.3390/M1596 - 23 Feb 2023
Abstract
1,2,5-Oxadiazole oxides (furoxans) are well known nitric oxide donors; among them, 4-fluorofuroxans have recently been found to be important photoinduced nitric oxide donors. In this research, it was shown that the reaction of 4,4′-dinitro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-dioxide with fluoro-containing reagents (tetrabutylammonium fluoride or cesium fluoride)
[...] Read more.
1,2,5-Oxadiazole oxides (furoxans) are well known nitric oxide donors; among them, 4-fluorofuroxans have recently been found to be important photoinduced nitric oxide donors. In this research, it was shown that the reaction of 4,4′-dinitro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-dioxide with fluoro-containing reagents (tetrabutylammonium fluoride or cesium fluoride) selectively gave the bis-substitution product 4,4′-difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-dioxide. The structure of the synthesized compound was established by elemental analysis, 13C, 19F-NMR and IR spectroscopy, and mass-spectrometry.
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(This article belongs to the Collection Heterocycle Reactions)
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