Synthesis and Electrochemistry of New Furylpyrazolino[60]fullerene Derivatives by Efficient Microwave Radiation

Efficient one-pot synthesis of new series of furylpyrazolino[60]fullerene derivatives was prepared by [3 + 2] cycloaddition reaction mediated with (diacetoxyiodo)benzene (PhI(OAc)2) as an oxidant in o-dichlorobenzene (ODCB) under microwave irradiation. Different techniques have been used to confirm the structural identity including FT-IR, fast atom bombardment (FAB)-mass, NMR, and single-crystal X-ray diffraction, in addition to investigating the photophysical properties and the electrochemical properties for the new compounds using UV-Vis spectra, fluorescence spectra, cyclic voltammetry, and square wave voltammetry. Three of these pyrazolino[60]fullerene compounds showed better electron affinity than the parent C60 in the ground state.

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Water Promoted One-pot Three-Step Synthesis of Novel N-Saccharin Isoxazolines/Isoxazoles Using KI/Oxone Under Ultrasonic Activation

Current Organic Chemistry ◽

10.2174/1385272823666190621115726 ◽

2019 ◽

Vol 23 (11) ◽

pp. 1270-1281 ◽

Cited By ~ 1

Author(s):

Hamza Tachallait ◽

Mohsine Driowya ◽

Eleuterio Álvarez ◽

Rachid Benhida ◽

Khalid Bougrin

Keyword(s):

Cycloaddition Reaction ◽

Hydroxylamine Hydrochloride ◽

Spectroscopic Techniques ◽

X Ray Diffraction ◽

Ultrasonic Activation ◽

One Pot ◽

Ultrasonic Probe ◽

X Ray ◽

X Ray Crystallography ◽

New Compounds

A green and efficient regioselective protocol was developed for the preparation of novel isoxazolines and isoxazoles of N-saccharin derivatives via the water-promoted cycloaddition reaction of nitrile oxides with alkenes and alkynes. It is noteworthy that KI/Oxone/water-promoted one-pot three-component reactions of aldehyde, hydroxylamine hydrochloride, and alkene or alkyne were observed to be very satisfactory. The synthesis of all adducts (4a-j/5a-j) has been carried out by this method with high to excellent yields (70-95%) at 25°C within 30 min, using ultrasonic probe. All the new compounds were thoroughly characterized by spectroscopic techniques and also 5b, 5c and 5f were structurally identified by single-crystal X-ray diffraction methods. X-ray crystallography structure analysis clearly supported the regioselectivity of the cycloaddition reaction.

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Nitroxide radicals appended to phthalonitriles: synthesis, structural characterization and photophysical properties

Acta Crystallographica Section C Structural Chemistry ◽

10.1107/s2053229621001832 ◽

2021 ◽

Vol 77 (3) ◽

pp. 137-143

Author(s):

Ismail Fidan ◽

Emel Onal ◽

Catherine Hirel

Keyword(s):

Magnetic Measurements ◽

Photophysical Properties ◽

Nucleophilic Aromatic Substitution ◽

Structural Studies ◽

Aromatic Substitution ◽

Nitronyl Nitroxide ◽

X Ray Diffraction ◽

X Ray ◽

Microwave Assisted ◽

Ft Ir

The syntheses of 4-[4-(4,4,5,5-tetramethyl-2-imidazoline-3-oxide-1-oxyl-2-yl)phenoxy]phthalonitrile (3, C21H19N4O3) and 4-[4-(4,4,5,5-tetramethyl-2-imidazoline-1-oxyl-2-yl)phenoxy]phthalonitrile (4) were carried out by microwave-assisted nucleophilic aromatic substitution of 4-nitrophthalonitrile (2) by the pre-formed 2-(4-hydroxyphenyl)-4,4,5,5-tetramethyl-2-imidazoline-3-oxide-1-oxyl (1). Compounds 3 and 4 were characterized unambiguously by a rich array of analyses, such as melting point, FT–IR, MALDI–TOF MS, elemental analysis, UV–Vis, CV, EPR, magnetic measurements and single-crystal X-ray diffraction. Structural studies demonstrate that the C—H...X and C—X...π (X = O and N) interactions in the radical nitronyl nitroxide groups play an important role in the assembly of the crystal structures. Moreover, cyclic voltammetry analyses show that the phthalonitrile substituent retains the redox properties of the Ullman radicals.

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Synthesis of new bimetallic phosphate (Al/Ag3PO4) and study for its Catalytic performance in the synthesis of 1,2-dihydro-l-phenyl-3H-naphth [1,2-e]-[1,3] oxazin-3-one derivatives

Mediterranean Journal of Chemistry ◽

10.13171/mjc02108091579elhallaoui ◽

2021 ◽

Vol 11 (3) ◽

pp. 215

Author(s):

Achraf El Hallaoui ◽

Tourya Ghailane ◽

Soukaina Chehab ◽

Youssef Merroun ◽

Rachida Ghailane ◽

...

Keyword(s):

Reaction Times ◽

Catalytic Performance ◽

X Ray Diffraction ◽

One Pot ◽

X Ray ◽

Silver Sulfate ◽

Triple Super Phosphate ◽

Aryl Aldehyde ◽

Ft Ir ◽

First Time

This work aims to prepare a new bimetallic phosphate catalyst using a new simple and effective method. This new catalyst was ready for the first time by a modification of Triple Super Phosphate (TSP) fertilizer with silver sulfate (AgSO4), followed by the impregnation of the aluminum atoms using aluminum nitrate (Al(NO3)3). The use of Al/Ag3PO4, for the first time as a heterogeneous catalyst in organic chemistry, offers a new, efficient, and green pathway for synthesizing 1,2-dihydro-l-phenyl-3H-naphth[1,2-e]-[1,3]oxazin-3-one derivatives by one-pot three-component cyclocondensation of b-naphthol, aryl aldehyde, and urea. The structure and the morphology of the prepared catalyst were characterized by spectroscopic methods such as X-Ray Diffraction (XRD), Fourier Transform Infrared spectroscopy (FT-IR), and dispersive X-ray spectrometry coupled with a scanning electron microscope (EDX-SEM). In addition, the optimization of the reaction parameters was carried out considering the effect of catalyst amount, the temperature, and the solvent. The procedure described herein allowed a comfortable preparation of oxazine derivatives with excellent yields, short reaction times, and in the absence of organic solvent.

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Fe-Doped UiO-66 Combined with ZnIn2S4 for Adsorption and Degradation of RhB Under Visible Light

NANO ◽

10.1142/s1793292020500897 ◽

2020 ◽

Vol 15 (07) ◽

pp. 2050089

Author(s):

Litong Niu ◽

Shaoping Hu ◽

Yali Ma ◽

Mingming Wang ◽

Bolin Lv ◽

...

Keyword(s):

Visible Light ◽

Electrochemical Impedance ◽

Diffuse Reflectance Spectroscopy ◽

Photogenerated Electron ◽

Impedance Spectrum ◽

Solvothermal Reaction ◽

Electrochemical Impedance Spectrum ◽

X Ray Diffraction ◽

One Pot ◽

Ft Ir

Novel ZnIn2S4/FeUiO-66 (ZFeU) photocatalyst with different proportion of FeUiO-66 has been successfully prepared by a facile one-pot solvothermal reaction. The as-synthesized nanocomposites have been thoroughly characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM), Fourier transform-infrared spectroscopy (FT-IR), UV-Vis diffuse reflectance spectroscopy (UV-Vis DRS), Brunauer–Emmett–Teller (BET) characterization, photoluminescence (PL) analysis and electrochemical impedance spectrum (EIS). The photocatalytic performance of ZFeU nanocomposites for the photodegradation of RhB under visible light irradiation was better than that of ZnIn2S4 and FeUiO-66 alone. The experiment results showed the 20% ZFeU nanocomposites had the best photocatalytic properties. At the same time, a probable mechanism was discussed and it was believed that introduction of FeUiO-66 on ZnIn2S4 would minimize the recombination of photogenerated electron-hole pairs, leading to the enhancement of the photocatalytic activity.

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Water-Soluble O-, S- and Se-Functionalized Cyclic Acetyl-triaza-phosphines. Synthesis, Characterization and Application in Catalytic Azide-alkyne Cycloaddition

Molecules ◽

10.3390/molecules25225479 ◽

2020 ◽

Vol 25 (22) ◽

pp. 5479

Author(s):

Abdallah Mahmoud ◽

Piotr Smoleński ◽

M. Guedes da Silva ◽

Armando Pombeiro

Keyword(s):

Cycloaddition Reaction ◽

Structural Features ◽

Water Soluble ◽

31P Nmr Spectroscopy ◽

The Novel ◽

X Ray Diffraction ◽

One Pot ◽

Hirshfeld Surfaces ◽

The One ◽

High Yields

The 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA) derivatives, viz. the already reported 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane 5-oxide (DAPTA=O, 1), the novel 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane-5-sulfide (DAPTA=S, 2), and 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane-5-selenide (DAPTA=Se, 3), have been synthesized under mild conditions. They are soluble in water and most common organic solvents and have been characterized using 1H and 31P NMR spectroscopy and, for 2 and 3, also by single crystal X-ray diffraction. The effect of O, S, or Se at the phosphorus atom on the structural features of the compounds has been investigated, also through the analyses of Hirshfeld surfaces. The presence of 1–3 enhances the activity of copper for the catalytic azide-alkyne cycloaddition reaction in an aqueous medium. The combination of cheaply available copper (II) acetate and compound 1 has been used as a catalyst for the one-pot and 1,4-regioselective procedure to obtain 1,2,3-triazoles with high yields and according to ‘click rules’.

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Synthesis and photophysical properties of zinc phthalocyanines substituted with quinolinoxy group

Journal of Porphyrins and Phthalocyanines ◽

10.1142/s108842460900156x ◽

2009 ◽

Vol 13 (12) ◽

pp. 1206-1213 ◽

Cited By ~ 1

Author(s):

Jinping Xue ◽

Lixuan Cai ◽

Naisheng Chen ◽

Jinling Huang

Keyword(s):

Absorption Spectra ◽

Electronic Absorption ◽

Elemental Analysis ◽

Fluorescence Spectra ◽

Electronic Absorption Spectra ◽

Photophysical Properties ◽

Electronic Spectroscopy ◽

Zinc Phthalocyanines ◽

New Compounds ◽

First Time

The synthesis of tetrasubstituted zinc phthalocyanines bearing quinolinoxy groups are reported for the first time. The new compounds have been characterized by elemental analysis, IR, MS and electronic spectroscopy. The photophysical properties, such as the electronic absorption spectra and fluorescence spectra, have also been investigated and discussed together with the influence of substituent position and organic solvents on these properties. The introduction of quinolinoxy group to the Pc ring was found to affect these photophysical properties to some extent.

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Platinum(II) Complex of Benzimidazole-Derived N-Heterocyclic Carbene: Synthesis, Characterization, and Photophysical Properties

VNU Journal of Science Natural Sciences and Technology ◽

10.25073/2588-1140/vnunst.5165 ◽

2021 ◽

Vol 37 (1) ◽

Author(s):

Nguyen Van Ha ◽

Trieu Thi Nguyet ◽

Doan Thanh Dat

Keyword(s):

Electronic Structure ◽

Magnetic Resonance ◽

Dft Calculations ◽

Photophysical Properties ◽

X Ray Diffraction ◽

One Pot ◽

Emission Process ◽

X Ray ◽

Absorption Shoulder ◽

Uv Lamp

Platinum(II) complex of benzimidazole-derived N-heterocyclic carbene with formula [PtCl2(DMSO)(bimy)] was successfully synthesized via one pot reaction between 1,3-diisopropyl benzimidazolium (bimy×HBr), Ag2O and [PtCl2(DMSO)] (DMSO = dimethyl sulfoxide). The complex was characterized by means of multinuclear (1H and 13C{1H}) magnetic resonance and single crystal X-ray diffraction (XRD). The UV-Vis absorption spectra of the compound show an absorption shoulder above 300 nm. Under excitation by 285 nm UV lamp, solution of the compound in DCM is highly emissive showing emission maxima at around 410 nm. DFT calculations were also carried out for the complex to gain insight on its electronic structure and the nature of electronic transition involved in the absorption/emission process.

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Ag2O/GO/TiO2 Composite Nanostructure: an efficient heterogeneous catalyst for one pot synthesis of Bis (dihydropyrimidinone) and tetrahydro-4H-chromenes derivatives

10.21203/rs.3.rs-240323/v1 ◽

2021 ◽

Author(s):

Fatemeh Samandi Zadeh ◽

Mohammad Kazem Mohammadi ◽

Ayeh Raeiatzadeh ◽

Neda Hasanzadeh

Keyword(s):

Condensation Reaction ◽

Aromatic Aldehydes ◽

Synthesis Methods ◽

X Ray Diffraction ◽

One Pot ◽

Transmission Electron ◽

One Pot Condensation ◽

Effective Synthesis ◽

Ft Ir ◽

Biginelli Condensation

Abstract The simple and efficient synthesis reaction was used for preparing Bis (dihydropyrimidinone) derivatives through Biginelli condensation reaction of terephthalic aldehyde, 1, 3-dicarbonyl compounds and (thio) urea or guanidine and tetrahydro-4H-chromenes via one pot condensation of aromatic aldehydes, malononitrile and dimedone with Ag2O/GO/TiO2 composite nanostructures as a catalyst. The structural functionalities and morphological observations of catalyst were obtained using characterization techniques of field emission scanning electron microscopy (FESEM), X-ray diffraction (XRD), Fourier transfer infrared (FT-IR) spectroscopy and transmission electron microscope (TEM). The structures of Bis (dihydropyrimidinone) and tetrahydro-4H-chromenes confirmed by FT- IR, NMR and mass spectroscopy. Excellent yields of the products, simple reaction process and simple work-up are attractive features of these effective synthesis methods.

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Anti-Mycobacterium tuberculosis Terpenoids from Resina Commiphora

Molecules ◽

10.3390/molecules24081475 ◽

2019 ◽

Vol 24 (8) ◽

pp. 1475 ◽

Cited By ~ 4

Author(s):

Chuan-Zhi Zhu ◽

Bin-Yuan Hu ◽

Jia-Wang Liu ◽

Yi Cai ◽

Xin-Chun Chen ◽

...

Keyword(s):

Nmr Spectra ◽

Human Cancer ◽

Cycloaddition Reaction ◽

Diels Alder ◽

Drug Resistant ◽

X Ray Diffraction ◽

Cellular Toxicity ◽

X Ray ◽

Human Cancer Cells ◽

New Compounds

Four new compounds including two new sesquiterpenoid dimers, commiphoroids E (1) and F (2), a new triterpenoid (3), and a new sesquiterpenoid (4), along with three known terpenoids (5−7) were isolated from Resina Commiphora, whose structures were identified by NMR spectra, HRESIMS, and X-ray diffraction analysis. Compounds 1 and 2 both bear an O-bridge ring and feature a plausible [4 + 2] Diels–Alder cycloaddition reaction. Antimycobacterial activities show that all the tested compounds (200 μM) could inhibit the growth of both sensitive and clinically multi-drug resistant (MDR) isolated strains. In addition, cellular toxicity of the isolates against human cancer cells and THP-1 monocyte cells was examined.

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Regio- and Diastereoselective Synthesis of Novel Polycyclic Pyrrolo[2,1-a]isoquinolines Bearing Indeno[1,2-b]quinoxaline Moieties by a Three-Component [3+2]-Cycloaddition Reaction

Synlett ◽

10.1055/s-0039-1690768 ◽

2019 ◽

Vol 31 (03) ◽

pp. 267-271 ◽

Cited By ~ 2

Author(s):

Firouz Matloubi Moghaddam ◽

Atiyeh Moafi ◽

Behzad Jafari ◽

Alexander Vilinger ◽

Peter Langer

Keyword(s):

Cycloaddition Reaction ◽

Reaction Times ◽

Dipolar Cycloaddition ◽

Diastereoselective Synthesis ◽

X Ray Diffraction ◽

Reaction Conditions ◽

One Pot ◽

Three Component Reaction ◽

Relative Stereochemistry ◽

High Yields

A regio- and diastereoselective synthesis of 2,3-dihydro-10b′H-spiro[indeno[1,2-b]quinoxaline-11,1′-pyrrolo[2,1-a]isoquinoline]-2′,3′-diylbis(phenylmethanone) derivatives containing four contiguous chiral stereocenters was achieved through 1,3-dipolar cycloaddition of isoquinolinium N-ylides in a one-pot three-component reaction. The desired products were obtained in short reaction times and in moderate to high yields (up to 92%) under relatively mild reaction conditions. The structure and relative stereochemistry of the desired product was confirmed by X-ray diffraction analysis.

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