Molbank

Open AccessShort Note

tert-Butyl (E)-3-oxo-2-(3-oxoisobenzofuran-1(3H)-ylidene)butanoate

by

Alexandra S. Chechulina

,

Ekaterina A. Knyazeva

,

Bin Kan

,

Tainan Duan

and

Oleg A. Rakitin

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. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Figure 1

Open AccessShort Note

6-Chloro-3-nitro-8-(phenylthio)-2-[(phenylthio)methyl] imidazo[1,2-a]pyridine

by

Romain Paoli-Lombardo

,

Nicolas Primas

,

Sébastien Hutter

,

Sandra Bourgeade-Delmas

,

Clotilde Boudot

,

Caroline Castera-Ducros

,

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,

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). Full article

(This article belongs to the Section Organic Synthesis)

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Scheme 1

Open AccessShort Note

3-Cyclohexyl-6-phenyl-1-(p-tolyl)pyrimidine-2,4(1H,3H)-dione

by

Francesco Messa

,

Serena Perrone

and

Antonio Salomone

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. Full article

(This article belongs to the Collection Molecules from Catalytic Processes)

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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.

by

Diego Cárdenas-Laverde

,

Diego Quiroga

and

Ericsson Coy-Barrera

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. Full article

(This article belongs to the Section Natural Products)

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Graphical abstract

Open AccessShort Note

Bis(2-phenylpyridinato,-C^2′,N)[4,4′-bis(4-Fluorophenyl)-6,6′-dimethyl-2,2′-bipyridine] Iridium(III) Hexafluorophosphate

by

Dimitrios Glykos

,

John C. Plakatouras

and

Gerasimos Malandrinos

Molbank 2023, 2023(2), M1610; https://doi.org/10.3390/M1610 - 24 Mar 2023

Abstract

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 (λ_em = 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 (λ_em = 562 nm). The quantum yield Φ was solvent-dependent (5% in acetonitrile and 19% in dichloromethane solutions, respectively). Full article

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Figure 1

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

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

Photodimerization of (E)-3-(2,6-Difluorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one in the Crystalline Solid State

by

Adriano Farias de Paula

,

Dari Cesarin-Sobrinho

and

José Carlos Netto-Ferreira

Molbank 2023, 2023(2), M1609; https://doi.org/10.3390/M1609 - 23 Mar 2023

Abstract

(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 (λ_irr = 300 nm) of chalcone 1 in the crystalline solid state resulted in the stereospecific formation of the syn-head-to-head photodimer (β-truxinic). Full article

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Figure 1

Open AccessShort Note

1-(2-Chlorophenyl)-6,7-dimethoxy-3-methyl-3,4-dihydroisoquinoline

by

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and

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. Full article

(This article belongs to the Section Organic Synthesis)

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Scheme 1

Open AccessCommunication

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

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

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

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

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

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

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

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

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

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

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

(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

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

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

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

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

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

by

Elizaveta D. Gladkova

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Tatiana G. Tolstikova

and

Nariman F. Salakhutdinov

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

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

by

Natalia V. Obruchnikova

and

Oleg A. Rakitin

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. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Scheme 1

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