Molbank

Open AccessShort Note

3-[4-(2-Phenylethyl)piperazin-1-yl]-7H-benzo[de]anthracen-7-one

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Molbank 2023, 2023(1), M1607; https://doi.org/10.3390/M1607 - 23 Mar 2023

Viewed by 609

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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Open AccessCommunication

Manganese(II) Bromide Coordination toward the Target Product and By-Product of the Condensation Reaction between 2-Picolylamine and Acenaphthenequinone

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Vera V. Khrizanforova

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Robert R. Fayzullin

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Yulia H. Budnikova

Molbank 2023, 2023(1), M1606; https://doi.org/10.3390/M1606 - 22 Mar 2023

Cited by 1 | Viewed by 545

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 Special Issue Molecules from Side Reactions II)

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Figure 1

Open AccessShort Note

[6-(Thiophen-2-yl)-2,2′-bipyridine]bis(triphenylphosphine) Copper(I) Tetrafluoroborate

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Panagiotis Kouvatsis

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Dimitrios Glykos

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John C. Plakatouras

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Gerasimos Malandrinos

Molbank 2023, 2023(1), M1605; https://doi.org/10.3390/M1605 - 16 Mar 2023

Viewed by 1041

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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Graphical abstract

Open AccessCommunication

Synthesis of 2-[2-(Ethoxymethoxy)phenyl]spiro[cyclopropane-1,2′-indene]-1′,3′-dione

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Molbank 2023, 2023(1), M1604; https://doi.org/10.3390/M1604 - 14 Mar 2023

Viewed by 710

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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Graphical abstract

Open AccessShort 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

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Joana L. C. Sousa

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Hélio M. T. Albuquerque

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Artur M. S. Silva

Molbank 2023, 2023(1), M1603; https://doi.org/10.3390/M1603 - 12 Mar 2023

Viewed by 673

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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Figure 1

Open AccessShort Note

New 2-(2,4-Dihydroxyphenyl)benzimidazolines

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Yordan Stremski

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Maria Bachvarova

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Desislava Kirkova

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Stela Statkova-Abeghe

Molbank 2023, 2023(1), M1602; https://doi.org/10.3390/M1602 - 10 Mar 2023

Viewed by 575

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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Graphical abstract

Open AccessShort Note

2-[2,6-Diisopropylphenyl]-4-phenyl-5H-5,9b[1′,2′]-benzonaphtho[1,2-b]pyrrol-2-ium Tetrafluoroborate

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Molbank 2023, 2023(1), M1601; https://doi.org/10.3390/M1601 - 10 Mar 2023

Viewed by 689

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 (λ_em = 516 nm) and in the solid state (λ_em = 517 nm) with relatively high to moderate quantum yields (Φ_F(CH2Cl2) = 0.63; Φ_F(solid) = 0.34). Full article

(This article belongs to the Section Structure Determination)

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Figure 1

Open AccessShort Note

(Z)-5-Benzylidene-4-phenyl-2-(p-tolyl)-4,5-dihydrooxazole

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Molbank 2023, 2023(1), M1600; https://doi.org/10.3390/M1600 - 06 Mar 2023

Viewed by 814

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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Figure 1

Open AccessCommunication

Synthesis, Characterization and Chemistry of Tetrakis(Propargylisocyanide) Copper(I) Complex

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Alexandre Quelhas

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Thierry Roisnel

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Jean-Claude Guillemin

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Yann Trolez

Molbank 2023, 2023(1), M1599; https://doi.org/10.3390/M1599 - 02 Mar 2023

Viewed by 719

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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Scheme 1

Open AccessShort Note

3-(5-Phenyl-2H-tetrazol-2-yl)pyridine

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Ivan S. Ershov

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Kirill A. Esikov

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Olga M. Nesterova

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Mariya A. Skryl’nikova

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Andrey V. Khramchikhin

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Nadezda T. Shmaneva

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Ivan S. Chernov

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Ekaterina N. Chernova

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Aleksandra M. Puzyk

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Eugene V. Sivtsov

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Yuliya N. Pavlyukova

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Rostislav E. Trifonov

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Vladimir A. Ostrovskii

Molbank 2023, 2023(1), M1598; https://doi.org/10.3390/M1598 - 28 Feb 2023

Viewed by 724

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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Open AccessCommunication

Synthesis of a Novel 9-O Berberine Derivative and Evaluation of Its Hypoglycemic Effect

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Elizaveta D. Gladkova

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Tatiana G. Tolstikova

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Nariman F. Salakhutdinov

Molbank 2023, 2023(1), M1597; https://doi.org/10.3390/M1597 - 24 Feb 2023

Viewed by 643

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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Open AccessShort Note

4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide

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Natalia V. Obruchnikova

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Oleg A. Rakitin

Molbank 2023, 2023(1), M1596; https://doi.org/10.3390/M1596 - 23 Feb 2023

Viewed by 651

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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Scheme 1

Open AccessShort Note

4,4-Difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(naphthalen-2-yl)-4-bora-3a,4a-diaza-s-indacene

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Molbank 2023, 2023(1), M1595; https://doi.org/10.3390/M1595 - 23 Feb 2023

Viewed by 611

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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Scheme 1

Open AccessShort Note

1-(4-Bromo-2,3,5,6-tetrafluoropheyl)-3-(3-phenylbenzyl)-4-methylimidazolium Bromide

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Udari A. I. Acharige

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Priya D. Parsot

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Graham C. Saunders

Molbank 2023, 2023(1), M1594; https://doi.org/10.3390/M1594 - 22 Feb 2023

Viewed by 833

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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Graphical abstract

Open AccessShort Note

(E)-1-(5-Methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one Oxime

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Bakr F. Abdel-Wahab

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Abdelbasset A. Farahat

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Benson M. Kariuki

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Gamal A. El-Hiti

Molbank 2023, 2023(1), M1593; https://doi.org/10.3390/M1593 - 21 Feb 2023

Cited by 1 | Viewed by 705

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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Graphical abstract

Open AccessShort 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

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Ilfat Z. Rakhmatullin

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Vladimir V. Klochkov

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Svetlana A. Lisovskaya

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Elena Yu. Trizna

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Denis Yu. Grishaev

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Airat R. Kayumov

Molbank 2023, 2023(1), M1592; https://doi.org/10.3390/M1592 - 17 Feb 2023

Viewed by 658

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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Graphical abstract

Open AccessShort Note

2,9-Dimethyl-4H-oxazolo[5’,4’:4,5]pyrano[3,2-f]quinolin-4-one

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Evangelia-Eirini N. Vlachou

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Thomas D. Balalas

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Dimitra J. Hadjipavlou-Litina

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Konstantinos E. Litinas

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Matina Douka

Molbank 2023, 2023(1), M1591; https://doi.org/10.3390/M1591 - 17 Feb 2023

Viewed by 601

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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Open AccessShort 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

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Andrey N. Komogortsev

and

Valeriya G. Melekhina

Molbank 2023, 2023(1), M1590; https://doi.org/10.3390/M1590 - 16 Feb 2023

Viewed by 718

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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Graphical abstract

Open AccessShort Note

Triethylammonium 2-(3-Hydroxy-2-oxoindolin-3-yl)-5,5-dimethyl-3-oxocyclohex-1-en-1-olate

by

Yuliya E. Ryzhkova

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Fedor V. Ryzhkov

and

Michail N. Elinson

Molbank 2023, 2023(1), M1589; https://doi.org/10.3390/M1589 - 15 Feb 2023

Viewed by 718

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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Graphical abstract

Open AccessShort Note

3-Methyl-1-phenyl-4-thioacetylpyrazol-5-one

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Molbank 2023, 2023(1), M1588; https://doi.org/10.3390/M1588 - 15 Feb 2023

Viewed by 726

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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Figure 1

Open AccessShort Note

2-(1H-Imidazol-2-yl)-2,3-dihydro-1H-perimidine

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Molbank 2023, 2023(1), M1587; https://doi.org/10.3390/M1587 - 15 Feb 2023

Viewed by 885

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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Figure 1

Open AccessShort Note

Dibenzyl-(1S*,2S*)-2,3-dihydro-1H-indene-1,2-dicarboxylate

by

Diego Olivieri

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Riccardo Tarroni

and

Carla Carfagna

Molbank 2023, 2023(1), M1586; https://doi.org/10.3390/M1586 - 15 Feb 2023

Viewed by 605

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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(Z)-2′-((Adamantan-1-yl)thio)-1,1′-dimethyl-2′,3′-dihydro-[2,4′-biimidazolylidene]-4,5,5′(1H,1′H,3H)-trione

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Molbank 2023, 2023(1), M1585; https://doi.org/10.3390/M1585 - 14 Feb 2023

Viewed by 732

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 Special Issue Molecules from Side Reactions II)

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Ethyl 12-Sulfamoyl-abieta-8,11,13-trien-18-oate

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Molbank 2023, 2023(1), M1584; https://doi.org/10.3390/M1584 - 13 Feb 2023

Viewed by 647

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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Open AccessShort Note

4-Benzoyl-2-(4-bromophenyl)-1-(4-methoxyphenyl)-1,2-dihydropyrimidino[4,3-c][1,4]benzoxazine-3,5-dione

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Ekaterina E. Khramtsova

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Maksim V. Dmitriev

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Andrey N. Maslivets

Molbank 2023, 2023(1), M1583; https://doi.org/10.3390/M1583 - 08 Feb 2023

Viewed by 679

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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Open AccessCommunication

New Preparation of Ferrocene Carboxylic Acid Benzotriazol-1-yl Ester

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Molbank 2023, 2023(1), M1582; https://doi.org/10.3390/M1582 - 06 Feb 2023

Viewed by 674

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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Open AccessCommunication

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

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Anna Nefedova

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Alexander Ovsyannikov

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Igor Litvinov

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Svetlana Solovieva

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Igor Antipin

Molbank 2023, 2023(1), M1581; https://doi.org/10.3390/M1581 - 06 Feb 2023

Viewed by 836

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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Open AccessShort Note

Methyl 9-(2-Iminothiazol-3(2H)-yl)-9-oxononanoate

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Gabriele Micheletti

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Natalia Calonghi

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Carla Boga

Molbank 2023, 2023(1), M1580; https://doi.org/10.3390/M1580 - 04 Feb 2023

Viewed by 1047

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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Open AccessShort Note

Methyl 9-(1-methyl-1H-indol-3-yl)-9-oxononanoate

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Gabriele Micheletti

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Carla Boga

Molbank 2023, 2023(1), M1579; https://doi.org/10.3390/M1579 - 04 Feb 2023

Viewed by 751

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

Open AccessShort 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 718

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

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