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Molbank, Volume 2023, Issue 1 (March 2023) – 77 articles

Cover Story (view full-size image): The novel visible-emitting fluorophore 2,7-bis(pyridin-3-ylethynyl)fluoren-9-one [(3-PyE)2FO] was successfully prepared via the Sonogashira coupling reaction and its full characterization is presented. The absorption and emission properties of (3-PyE)2FO were investigated both in solution and in solid states. The UV-Vis spectrum of (3-PyE)2FO in CHCl3 exhibited four maxima centered at 304, 339, 349 and 436 nm, respectively, and a strong photoluminescence emission was observed at 554 nm. Solid-state measurements showed broad absorption in the diffuse reflectance spectrum in the 200−500 nm range and a strong emission band of 553 nm, similar to that observed in solution. Further studies are ongoing in our laboratories to evaluate the potential use of (3-PyE)2FO as a building block for the formation of luminescent supramolecular assemblies. View this paper
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7 pages, 2239 KiB  
Short Note
3-[4-(2-Phenylethyl)piperazin-1-yl]-7H-benzo[de]anthracen-7-one
by Romans Fridmans, Aleksandrs Puckins, Sergejs Osipovs, Sergey Belyakov and Elena Kirilova
Molbank 2023, 2023(1), M1607; https://doi.org/10.3390/M1607 - 23 Mar 2023
Viewed by 1122
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. Full article
(This article belongs to the Section Organic Synthesis)
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5 pages, 1305 KiB  
Communication
Manganese(II) Bromide Coordination toward the Target Product and By-Product of the Condensation Reaction between 2-Picolylamine and Acenaphthenequinone
by Vera V. Khrizanforova, Robert R. Fayzullin and Yulia H. Budnikova
Molbank 2023, 2023(1), M1606; https://doi.org/10.3390/M1606 - 22 Mar 2023
Cited by 1 | Viewed by 1069
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. Full article
(This article belongs to the Collection Molecules from Side Reactions)
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8 pages, 2118 KiB  
Short Note
[6-(Thiophen-2-yl)-2,2′-bipyridine]bis(triphenylphosphine) Copper(I) Tetrafluoroborate
by Panagiotis Kouvatsis, Dimitrios Glykos, John C. Plakatouras and Gerasimos Malandrinos
Molbank 2023, 2023(1), M1605; https://doi.org/10.3390/M1605 - 16 Mar 2023
Cited by 1 | Viewed by 1766
Abstract
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. Full article
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6 pages, 579 KiB  
Communication
Synthesis of 2-[2-(Ethoxymethoxy)phenyl]spiro[cyclopropane-1,2′-indene]-1′,3′-dione
by Olga A. Ivanova, Vitaly V. Shorokhov, Ivan A. Andreev, Nina K. Ratmanova, Victor B. Rybakov, Elena D. Strel’tsova and Igor V. Trushkov
Molbank 2023, 2023(1), M1604; https://doi.org/10.3390/M1604 - 14 Mar 2023
Viewed by 1445
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. Full article
(This article belongs to the Section Organic Synthesis)
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6 pages, 1153 KiB  
Short Note
6-[(2S,3R)-3-(2,4-Difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl]-5-fluoropyrimidine-4-carbaldehyde
by Joana L. C. Sousa, Hélio M. T. Albuquerque and Artur M. S. Silva
Molbank 2023, 2023(1), M1603; https://doi.org/10.3390/M1603 - 12 Mar 2023
Viewed by 1164
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. Full article
(This article belongs to the Section Organic Synthesis)
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6 pages, 706 KiB  
Short Note
New 2-(2,4-Dihydroxyphenyl)benzimidazolines
by Yordan Stremski, Maria Bachvarova, Desislava Kirkova and Stela Statkova-Abeghe
Molbank 2023, 2023(1), M1602; https://doi.org/10.3390/M1602 - 10 Mar 2023
Viewed by 1109
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. Full article
(This article belongs to the Collection Heterocycle Reactions)
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8 pages, 1478 KiB  
Short Note
2-[2,6-Diisopropylphenyl]-4-phenyl-5H-5,9b[1′,2′]-benzonaphtho[1,2-b]pyrrol-2-ium Tetrafluoroborate
by Masaru Tanaka, Shota Kamiyama, Akihiko Ishii and Norio Nakata
Molbank 2023, 2023(1), M1601; https://doi.org/10.3390/M1601 - 10 Mar 2023
Viewed by 1436
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 CH2Cl2em = 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). Full article
(This article belongs to the Section Structure Determination)
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6 pages, 1924 KiB  
Short Note
(Z)-5-Benzylidene-4-phenyl-2-(p-tolyl)-4,5-dihydrooxazole
by Nobuyoshi Morita, Hitomi Chiaki, Shino Aonuma, Kosaku Tanaka III, Yoshimitsu Hashimoto and Osamu Tamura
Molbank 2023, 2023(1), M1600; https://doi.org/10.3390/M1600 - 06 Mar 2023
Cited by 1 | Viewed by 1461
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. Full article
(This article belongs to the Topic Catalysis: Homogeneous and Heterogeneous)
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6 pages, 778 KiB  
Communication
Synthesis, Characterization and Chemistry of Tetrakis(Propargylisocyanide) Copper(I) Complex
by Alexandre Quelhas, Thierry Roisnel, Jean-Claude Guillemin and Yann Trolez
Molbank 2023, 2023(1), M1599; https://doi.org/10.3390/M1599 - 02 Mar 2023
Viewed by 1337
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. Full article
(This article belongs to the Section Organic Synthesis)
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12 pages, 3080 KiB  
Short Note
3-(5-Phenyl-2H-tetrazol-2-yl)pyridine
by Ivan S. Ershov, Kirill A. Esikov, Olga M. Nesterova, Mariya A. Skryl’nikova, Andrey V. Khramchikhin, Nadezda T. Shmaneva, Ivan S. Chernov, Ekaterina N. Chernova, Aleksandra M. Puzyk, Eugene V. Sivtsov, Yuliya N. Pavlyukova, Rostislav E. Trifonov and Vladimir A. Ostrovskii
Molbank 2023, 2023(1), M1598; https://doi.org/10.3390/M1598 - 28 Feb 2023
Viewed by 1404
Abstract
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. Full article
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6 pages, 1169 KiB  
Communication
Synthesis of a Novel 9-O Berberine Derivative and Evaluation of Its Hypoglycemic Effect
by Elizaveta D. Gladkova, Nicolae Valutsa, Sergey A. Borisov, Mikhail V. Khvostov, Olga A. Luzina, Tatiana G. Tolstikova and Nariman F. Salakhutdinov
Molbank 2023, 2023(1), M1597; https://doi.org/10.3390/M1597 - 24 Feb 2023
Viewed by 1106
Abstract
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. Full article
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3 pages, 321 KiB  
Short Note
4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide
by Natalia V. Obruchnikova and Oleg A. Rakitin
Molbank 2023, 2023(1), M1596; https://doi.org/10.3390/M1596 - 23 Feb 2023
Viewed by 1032
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. Full article
(This article belongs to the Collection Heterocycle Reactions)
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5 pages, 2853 KiB  
Short Note
4,4-Difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(naphthalen-2-yl)-4-bora-3a,4a-diaza-s-indacene
by Elena F. Sagitova, Olga V. Petrova, Denis N. Tomilin, Igor A. Ushakov, Lyubov N. Sobenina and Boris A. Trofimov
Molbank 2023, 2023(1), M1595; https://doi.org/10.3390/M1595 - 23 Feb 2023
Cited by 1 | Viewed by 938
Abstract
The title compound, 4,4-difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(2-naphthalen-2-yl)-4-bora-3a,4a-diaza-s-indacene (1), was synthesized for the first time in a 62% yield by the P2O5-promoted condensation of 2,2,2-trifluoro-1-[5-(naphthalen-2-yl)-1H-pyrrol-2-yl]-ethan-1-ol (2) with 3-phenyl-5-(1H-pyrrol-2-yl)isoxazole (3) followed by [...] Read more.
The title compound, 4,4-difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(2-naphthalen-2-yl)-4-bora-3a,4a-diaza-s-indacene (1), was synthesized for the first time in a 62% yield by the P2O5-promoted condensation of 2,2,2-trifluoro-1-[5-(naphthalen-2-yl)-1H-pyrrol-2-yl]-ethan-1-ol (2) with 3-phenyl-5-(1H-pyrrol-2-yl)isoxazole (3) followed by the oxidation of dipyrromethane 4 and the complexation of dipyrromethene thus formed with BF3. The product fluoresces in a long wave region (651–662 nm) with a high quantum yield (0.49–0.61). Full article
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7 pages, 2011 KiB  
Short Note
1-(4-Bromo-2,3,5,6-tetrafluoropheyl)-3-(3-phenylbenzyl)-4-methylimidazolium Bromide
by Udari A. I. Acharige, Priya D. Parsot and Graham C. Saunders
Molbank 2023, 2023(1), M1594; https://doi.org/10.3390/M1594 - 22 Feb 2023
Viewed by 1336
Abstract
In this paper, we report on the crystal structure of salt 1-(4-bromo-2,3,5,6-tetrafluorophenyl)-3-(3-phenylbenzyl)-4-methylimidazolium bromide, 3, synthesized by the sequential nucleophilic attack of 4-methylimidazole on bromopentafluorobenzene and then 3-phenylbenzyl bromide. The salt was characterized by 1H, 13C, and 19F NMR spectroscopy and mass spectrometry. Full article
(This article belongs to the Section Structure Determination)
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7 pages, 2512 KiB  
Short Note
(E)-1-(5-Methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one Oxime
by Bakr F. Abdel-Wahab, Abdelbasset A. Farahat, Benson M. Kariuki and Gamal A. El-Hiti
Molbank 2023, 2023(1), M1593; https://doi.org/10.3390/M1593 - 21 Feb 2023
Cited by 3 | Viewed by 1296
Abstract
The reaction of 1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one (1) with excess hydroxylamine hydrochloride (2 mole equivalents) in dry ethanol afforded (E)-1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one oxime (2) in 86% yield. The structure of the new heterocycle 2 was confirmed using nuclear magnetic resonance spectroscopy, single crystal X-ray and elemental analysis. Full article
(This article belongs to the Collection Heterocycle Reactions)
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5 pages, 509 KiB  
Short Note
N-(((1S,5R)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)-3-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-ene/ane-2-carboxamido)-N,N-dimethylpropan-1-aminium Bromide
by Ilmir R. Gilfanov, Roman S. Pavelyev, Liliya E. Nikitina, Larisa L. Frolova, Alexey V. Popov, Ilfat Z. Rakhmatullin, Vladimir V. Klochkov, Svetlana A. Lisovskaya, Elena Yu. Trizna, Denis Yu. Grishaev and Airat R. Kayumov
Molbank 2023, 2023(1), M1592; https://doi.org/10.3390/M1592 - 17 Feb 2023
Cited by 2 | Viewed by 1227
Abstract
The synthesis of the title compounds was performed from (-)-cis-myrtanic and (-)-myrtenic acids. The compounds obtained were characterized using 1H- and 13C-NMR, IR, and high-resolution mass spectrometry. Despite the presence of quaternary ammonium moiety, both compounds had moderate antimicrobial activity with [...] Read more.
The synthesis of the title compounds was performed from (-)-cis-myrtanic and (-)-myrtenic acids. The compounds obtained were characterized using 1H- and 13C-NMR, IR, and high-resolution mass spectrometry. Despite the presence of quaternary ammonium moiety, both compounds had moderate antimicrobial activity with a MIC of 128 µg/mL on S. aureus and 512 µg/mL on E. coli. The antifungal activity was low on Candida isolates, while also comparable with conventional antimycotic (Fluconazole) on filamentous fungi. These data suggest that two bulky bicyclic terpene fragments apparently both increase lipophilicity and close the quaternary ammonium moiety located in the center of molecules and thus drastically decrease the antimicrobial potential of bipharmacophore. Full article
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7 pages, 887 KiB  
Short Note
2,9-Dimethyl-4H-oxazolo[5’,4’:4,5]pyrano[3,2-f]quinolin-4-one
by Evangelia-Eirini N. Vlachou, Thomas D. Balalas, Dimitra J. Hadjipavlou-Litina, Konstantinos E. Litinas and Matina Douka
Molbank 2023, 2023(1), M1591; https://doi.org/10.3390/M1591 - 17 Feb 2023
Cited by 1 | Viewed by 1084
Abstract
The new 2,9-dimethyl-4H-oxazolo[5’,4’:4,5]pyrano[3,2-f]quinolin-4-one was successfully prepared through the three-component iodine-catalyzed reaction of n-butyl vinyl ether with the new 8-amino-2-methyl-4H-chromeno[3,4-d]oxazol-4-one. The latter was prepared by the reduction of 2-methyl-8-nitro-4H-chromeno[3,4-d]oxazol-4-one with Pd/C [...] Read more.
The new 2,9-dimethyl-4H-oxazolo[5’,4’:4,5]pyrano[3,2-f]quinolin-4-one was successfully prepared through the three-component iodine-catalyzed reaction of n-butyl vinyl ether with the new 8-amino-2-methyl-4H-chromeno[3,4-d]oxazol-4-one. The latter was prepared by the reduction of 2-methyl-8-nitro-4H-chromeno[3,4-d]oxazol-4-one with Pd/C in a hydrogen atmosphere. The above nitro compound was synthesized by the condensation of N-(4-hydroxy-6-nitro-2-oxo-2H-chromen-3-yl)acetamide with P2O5 under microwave irradiation. The above acetamide derivative was prepared during the nitration of 2-methyl-4H-chromeno[3,4-d]oxazol-4-one with H2SO4 and KNO3. The structure of the newly synthesized compounds was confirmed by FT-IR, LC-MS, 1H-NMR, and 13C-NMR analyses. Preliminary biological tests show significant anti-lipid peroxidation activity for the title compound and the other synthesized new intermediates, as well as interesting soybean lipoxygenase inhibition for acetamide 2 (IC50 55 μM) and nitro-compound 3 (IC50 27 μM). Full article
(This article belongs to the Section Organic Synthesis)
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5 pages, 1414 KiB  
Short Note
(2R,6′R,E)-3′-(1-Aminoethylidene)-7-chloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexane]-2′,3,4′-trione
by Boris V. Lichitsky, Andrey N. Komogortsev and Valeriya G. Melekhina
Molbank 2023, 2023(1), M1590; https://doi.org/10.3390/M1590 - 16 Feb 2023
Viewed by 1067
Abstract
A novel synthesis approach for griseofulvin derivatives was developed. The presented method is based on a two-stage process that includes preliminary acetylation of griseofulvic acid followed by condensation with ammonium acetate. The advantages of this protocol include readily available starting materials and a [...] Read more.
A novel synthesis approach for griseofulvin derivatives was developed. The presented method is based on a two-stage process that includes preliminary acetylation of griseofulvic acid followed by condensation with ammonium acetate. The advantages of this protocol include readily available starting materials and a simple target product isolation procedure. The structure of the synthesized polycyclic compound was approved by 1H, 13C-NMR spectroscopy, high-resolution mass spectrometry with electrospray ionization (ESI-HRMS), and X-ray diffraction. Full article
(This article belongs to the Section Organic Synthesis)
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7 pages, 1807 KiB  
Short Note
Triethylammonium 2-(3-Hydroxy-2-oxoindolin-3-yl)-5,5-dimethyl-3-oxocyclohex-1-en-1-olate
by Yuliya E. Ryzhkova, Fedor V. Ryzhkov and Michail N. Elinson
Molbank 2023, 2023(1), M1589; https://doi.org/10.3390/M1589 - 15 Feb 2023
Cited by 1 | Viewed by 1226
Abstract
In recent years, the application of privileged structures has become a powerful approach in the discovery of new biologically active molecules. Ion pairing is a strategy used to enhance the permeation of ionized topical drugs. A convenient and efficient method for the synthesis [...] Read more.
In recent years, the application of privileged structures has become a powerful approach in the discovery of new biologically active molecules. Ion pairing is a strategy used to enhance the permeation of ionized topical drugs. A convenient and efficient method for the synthesis of triethylammonium 2-(3-hydroxy-2-oxoindolin-3-yl)-5,5-dimethyl-3-oxocyclohex-1-en-1-olate has been developed. The presented protocol includes an aldol reaction and the formation of an ammonium salt. Triethylamine is both a reactant and a catalyst in the process. The structure of the synthesized title compound has been established by 1H, 13C-NMR and IR spectroscopy, mass spectrometry, and elemental analysis. Full article
(This article belongs to the Collection Heterocycle Reactions)
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7 pages, 1626 KiB  
Short Note
3-Methyl-1-phenyl-4-thioacetylpyrazol-5-one
by Zhanina Petkova, Rusi Rusew, Boris Shivachev and Vanya Kurteva
Molbank 2023, 2023(1), M1588; https://doi.org/10.3390/M1588 - 15 Feb 2023
Viewed by 1234
Abstract
The novel compound 3-methyl-1-phenyl-4-thioacetylpyrazol-5-one is obtained in excellent yield via a thionation of the corresponding oxygen analogue. The product is isolated in pure form using column chromatography and is characterised using 1D and 2D NMR experiments, ATR IR and HRMS spectra, and single-crystal [...] Read more.
The novel compound 3-methyl-1-phenyl-4-thioacetylpyrazol-5-one is obtained in excellent yield via a thionation of the corresponding oxygen analogue. The product is isolated in pure form using column chromatography and is characterised using 1D and 2D NMR experiments, ATR IR and HRMS spectra, and single-crystal XRD. Full article
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10 pages, 1746 KiB  
Short Note
2-(1H-Imidazol-2-yl)-2,3-dihydro-1H-perimidine
by Zhanina Petkova, Rusi Rusew, Snezhana Bakalova, Boris Shivachev and Vanya Kurteva
Molbank 2023, 2023(1), M1587; https://doi.org/10.3390/M1587 - 15 Feb 2023
Viewed by 1406
Abstract
The novel compound 2-(1H-imidazol-2-yl)-2,3-dihydro-1H-perimidine was obtained in very good yield via a known eco-friendly protocol. The product was isolated in pure form as a solvate by simple filtration from the crude mixture. Its structure was assigned by 1D and 2D NMR experiments and [...] Read more.
The novel compound 2-(1H-imidazol-2-yl)-2,3-dihydro-1H-perimidine was obtained in very good yield via a known eco-friendly protocol. The product was isolated in pure form as a solvate by simple filtration from the crude mixture. Its structure was assigned by 1D and 2D NMR experiments and was confirmed by high resolution MS and single crystal XRD. The temperature of methanol release was determined by DSC and the energy of the process theoretically estimated. Full article
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5 pages, 328 KiB  
Short Note
Dibenzyl-(1S*,2S*)-2,3-dihydro-1H-indene-1,2-dicarboxylate
by Diego Olivieri, Riccardo Tarroni and Carla Carfagna
Molbank 2023, 2023(1), M1586; https://doi.org/10.3390/M1586 - 15 Feb 2023
Viewed by 932
Abstract
The synthesis of dibenzyl-(1S*,2S*)-2,3-dihydro-1H-indene-1,2-dicarboxylate has been realized through a diastereospecific bis-alkoxycarbonylation reaction, which starts from the cheap and easily available 1H-indene, benzyl alcohol, and carbon monoxide. The catalyst is formed in situ by mixing Pd(TFA) [...] Read more.
The synthesis of dibenzyl-(1S*,2S*)-2,3-dihydro-1H-indene-1,2-dicarboxylate has been realized through a diastereospecific bis-alkoxycarbonylation reaction, which starts from the cheap and easily available 1H-indene, benzyl alcohol, and carbon monoxide. The catalyst is formed in situ by mixing Pd(TFA)2, the ligand N2,N3-bis(2,6-dimethylphenyl)butane-2,3-diimine, p-benzoquinone is used as an oxidant, and benzyl alcohol acts both as a nucleophile and as the main solvent. Full article
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Graphical abstract

6 pages, 1093 KiB  
Short Note
(Z)-2′-((Adamantan-1-yl)thio)-1,1′-dimethyl-2′,3′-dihydro-[2,4′-biimidazolylidene]-4,5,5′(1H,1′H,3H)-trione
by Vladimir Burmistrov, Vladimir Mokhov, Robert R. Fayzullin and Gennady M. Butov
Molbank 2023, 2023(1), M1585; https://doi.org/10.3390/M1585 - 14 Feb 2023
Viewed by 1234
Abstract
The title compound, (Z)-2′-((adamantan-1-yl)thio)-1,1′-dimethyl-2′,3′-dihydro-[2,4′-biimidazolylidene]-4,5,5′(1H,1′H,3H)-trione, was found to be a by-product of the reaction of 1,3-dehydroadamantane with 3-methyl-2-thioxoimidazolidin-4-one and characterized via single-crystal X-ray diffraction. Full article
(This article belongs to the Collection Molecules from Side Reactions)
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6 pages, 1545 KiB  
Short Note
Ethyl 12-Sulfamoyl-abieta-8,11,13-trien-18-oate
by Evgeniy S. Izmest’ev, Svetlana V. Pestova, Darya P. Gerasimova, Olga B. Babaeva, Olga A. Lodochnikova, Liliya E. Nikitina, Airat R. Kayumov and Svetlana A. Rubtsova
Molbank 2023, 2023(1), M1584; https://doi.org/10.3390/M1584 - 13 Feb 2023
Cited by 1 | Viewed by 1115
Abstract
We synthesized the novel compound ethyl 12-sulfamoyl-abieta-8,11,13-trien-18-oate in good yield from ethyl 12-sulfo-abieta-8,11,13-trien-18-oate via a two-step protocol. The product was comprehensively characterized by one- and two-dimensional NMR methods, single-crystal X-ray diffraction, IR spectroscopy, and high-resolution mass spectrometry. Full article
(This article belongs to the Section Structure Determination)
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4 pages, 1133 KiB  
Short Note
4-Benzoyl-2-(4-bromophenyl)-1-(4-methoxyphenyl)-1,2-dihydropyrimidino[4,3-c][1,4]benzoxazine-3,5-dione
by Ekaterina E. Khramtsova, Maksim V. Dmitriev and Andrey N. Maslivets
Molbank 2023, 2023(1), M1583; https://doi.org/10.3390/M1583 - 08 Feb 2023
Viewed by 1111
Abstract
The reaction of 3-benzoylpyrrolo[2,1-c][1,4]benzoxazin-1,2,4-trione with N-(4-bromophenyl)-1-(4-methoxyphenyl)methanimine under thermolytical conditions afforded 4-benzoyl-2-(4-bromophenyl)-1-(4-methoxyphenyl)-1,2-dihydropyrimidino[4,3-c][1,4]benzoxazine-3,5-dione in a good yield. The reaction proceeded via in situ generation of a reactive intermediate, acyl(imidoyl)ketene. The compound was fully characterized. Full article
(This article belongs to the Collection Heterocycle Reactions)
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4 pages, 781 KiB  
Communication
New Preparation of Ferrocene Carboxylic Acid Benzotriazol-1-yl Ester
by Lin-Yuan Zhang, Li-Jun Xu, Ya-Wen Wang and Yu Peng
Molbank 2023, 2023(1), M1582; https://doi.org/10.3390/M1582 - 06 Feb 2023
Viewed by 1245
Abstract
Ferrocene and its derivatives are very useful in the fields of chemistry, biomedicine and materials. Herein, a ferrocene derivative was synthesized in one step from benzotriazol-1-yl-oxytripyrrolidino-phosphonium hexafluorophosphate and ferrocenecarboxylic acid. Its accurate structure was determined by 1H and 13C NMR and [...] Read more.
Ferrocene and its derivatives are very useful in the fields of chemistry, biomedicine and materials. Herein, a ferrocene derivative was synthesized in one step from benzotriazol-1-yl-oxytripyrrolidino-phosphonium hexafluorophosphate and ferrocenecarboxylic acid. Its accurate structure was determined by 1H and 13C NMR and further confirmed by X-ray diffraction analysis of the corresponding single crystal. Full article
(This article belongs to the Section Organic Synthesis)
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6 pages, 778 KiB  
Communication
Synthesis and Crystal Structure of Ethyl 5-(4-Bromophenyl)-7-methyl-3-oxo-2,3-dihidro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate
by Artem Agarkov, Anna Nefedova, Alexander Ovsyannikov, Igor Litvinov, Svetlana Solovieva and Igor Antipin
Molbank 2023, 2023(1), M1581; https://doi.org/10.3390/M1581 - 06 Feb 2023
Viewed by 1372
Abstract
Thiazolopyrimidines are attractive to medical chemists as new antitumor agents due to their high inhibitory activity against the replication process of tumor cells and the easy modification of their structure by changing the number and nature of substituents. The presence of asymmetric C5 [...] Read more.
Thiazolopyrimidines are attractive to medical chemists as new antitumor agents due to their high inhibitory activity against the replication process of tumor cells and the easy modification of their structure by changing the number and nature of substituents. The presence of asymmetric C5 carbon atoms requires the development of racemic mixture separation procedures for these heterocycles. One of the most effective methods is the crystallization of a racemic compound in the form of a conglomerate. The prerequisite for such separation is the construction of chiral, supramolecular ensembles in the crystalline state. Halogen-π interactions were chosen as supramolecular synthons. In this context, ethyl 7-methyl-3-oxo-2,3-dihidro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate containing a 4-bromophenyl fragment at C5 was synthesized. The crystal structure of the resulting compound was established using SCXRD. The role of the halogen-π interaction on the formation of one-dimensional homochiral chains is revealed. Full article
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5 pages, 987 KiB  
Short Note
Methyl 9-(2-Iminothiazol-3(2H)-yl)-9-oxononanoate
by Gabriele Micheletti, Natalia Calonghi and Carla Boga
Molbank 2023, 2023(1), M1580; https://doi.org/10.3390/M1580 - 04 Feb 2023
Viewed by 1472
Abstract
Methyl 9-(2-iminothiazol-3(2H)-yl)-9-oxononanoate was synthesized through Schotten–Baumann type reaction between 2–aminothiazole and methyl 9-chloro-9-oxononanoate. The structure of the newly synthesized compound was elucidated based on 1H-NMR, 13C-NMR, DEPT, NOE, ESI-MS, FT-IR and UV-Vis spectroscopy. Full article
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3 pages, 477 KiB  
Short Note
Methyl 9-(1-methyl-1H-indol-3-yl)-9-oxononanoate
by Gabriele Micheletti and Carla Boga
Molbank 2023, 2023(1), M1579; https://doi.org/10.3390/M1579 - 04 Feb 2023
Viewed by 1447
Abstract
Methyl 9-(1-methyl-1H-indol-3-yl)-9-oxononanoate was synthesized using Friedel–Crafts acylation between N-methyl indole and methyl 9-chloro-9-oxononanoate. The structure of the newly synthesized compound was elucidated using 1H-NMR, 13C-NMR, NOESY-1D, ESI-MS, FT-IR, and UV-Vis spectroscopy. Full article
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Scheme 1

3 pages, 492 KiB  
Short Note
1-[2,6-Dimethyl-4-(pent-4-yn-1-yloxy)phenyl]-4-phenyl-1,2,4-triazolidine-3,5-dione
by Gary W. Breton
Molbank 2023, 2023(1), M1578; https://doi.org/10.3390/M1578 - 04 Feb 2023
Viewed by 1036
Abstract
Urazolyl radicals are a class of persistent nitrogen-centered radicals. In a previous work, we successfully formed self-assembled monolayers of substituted urazolyl radicals on gold surfaces. To extend the scope of these investigations, we sought to form a self-assembled monolayer using a urazolyl radical [...] Read more.
Urazolyl radicals are a class of persistent nitrogen-centered radicals. In a previous work, we successfully formed self-assembled monolayers of substituted urazolyl radicals on gold surfaces. To extend the scope of these investigations, we sought to form a self-assembled monolayer using a urazolyl radical species that we knew existed predominantly in the dimerized N-N form instead of existing predominantly as free N-centered radical species, as had previously been investigated. We successfully synthesized the precursor urazole compound needed to generate the desired urazolyl radical, and completely characterized its structure. Most importantly, it was determined that the alkyne functional group that is needed to adhere to the gold surface remained intact. Unfortunately, however, we only obtained ambiguous results from attempts at forming self-assembled monolayers of this species on gold. Full article
(This article belongs to the Section Structure Determination)
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Scheme 1

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