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

Molecules ◽  
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’.

scholarly journals Synthesis of a Novel Series of Cu(I) Complexes Bearing Alkylated 1,3,5-Triaza-7-phosphaadamantane as Homogeneous and Carbon-Supported Catalysts for the Synthesis of 1- and 2-Substituted-1,2,3-triazoles

Nanomaterials ◽  
2021 ◽  
Vol 11 (10) ◽  
pp. 2702
Author(s):  
Ivy L. Librando ◽  
Abdallah G. Mahmoud ◽  
Sónia A. C. Carabineiro ◽  
M. Fátima C. Guedes da Silva ◽  
Carlos F. G. C. Geraldes ◽  
...  
Keyword(s):  
Aqueous Medium ◽  
Sodium Azide ◽  
Supported Catalysts ◽  
Cycloaddition Reaction ◽  
Water Soluble ◽  
Terminal Alkynes ◽  
One Pot ◽  
Catalytic Systems ◽  
Immobilized Catalyst ◽  
High Yields

The N-alkylation of 1,3,5-triaza-7-phosphaadamantane (PTA) with ortho-, meta- and para-substituted nitrobenzyl bromide under mild conditions afforded three hydrophilic PTA ammonium salts, which were used to obtain a new set of seven water-soluble copper(I) complexes. The new compounds were fully characterized and their catalytic activity was investigated for the low power microwave assisted one-pot azide–alkyne cycloaddition reaction in homogeneous aqueous medium to obtain disubstituted 1,2,3-triazoles. The most active catalysts were immobilized on activated carbon (AC), multi-walled carbon nanotubes (CNT), as well as surface functionalized AC and CNT, with the most efficient support being the CNT treated with nitric acid and NaOH. In the presence of the immobilized catalyst, several 1,4-disubstituted-1,2,3-triazoles were obtained from the reaction of terminal alkynes, organic halides and sodium azide in moderate yields up to 80%. Furthermore, the catalyzed reaction of terminal alkynes, formaldehyde and sodium azide afforded 2-hydroxymethyl-2H-1,2,3-triazoles in high yields up to 99%. The immobilized catalyst can be recovered and recycled through simple workup steps and reused up to five consecutive cycles without a marked loss in activity. The described catalytic systems proceed with a broad substrate scope, under microwave irradiation in aqueous medium and according to “click rules”.

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 ◽  
2019 ◽  
Vol 31 (03) ◽  
pp. 267-271 ◽  
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.

scholarly journals Three Multi-Components Reaction: Synthesis and X-Ray Single-Crystal of Hydroacridinone-Based Hydrazino-S-Triazine Derivative as a New Class of Urease Inhibitor

Crystals ◽  
2019 ◽  
Vol 10 (1) ◽  
pp. 14 ◽  
Author(s):  
Assem Barakat ◽  
Saied M. Soliman ◽  
Ayman El-Faham ◽  
M. Ali ◽  
Abdullah Mohammed Al-Majid ◽  
...  
Keyword(s):  
Structural Features ◽  
Acetohydroxamic Acid ◽  
Orthorhombic Crystal System ◽  
Orthorhombic Crystal ◽  
One Pot ◽  
X Ray ◽  
New Class ◽  
Hirshfeld Surfaces ◽  
The One

The one-pot fashion of three multi-component reaction provides the desired hydroacridinone-based hydrazino-s-triazine scaffold 4. Compound 4 was crystallized in an orthorhombic crystal system and Pbca space group with a = 11.6271(2) Å, b = 18.2018(4) Å, c = 32.4721(6) Å, and α = β = γ = 90° with one formula unit per asymmetric unit and eight molecules per unit cell. Additionally, structural features, Hirshfeld surfaces, and DFT studies were also investigated. Its packing in the crystal is controlled by H…H (63.4%), O…H (12.7%), Cl…H (7.2%), N…H (4.7%), and C…H (10.2%) contacts, where the O…H and Cl…H contacts were found the strongest. In vitro urease inhibition evaluation showed that the hydroacridinone-based hydrazino-s-triazine is more active (IC50 = 17.9 ± 0.47 µM) than the standard acetohydroxamic acid (IC50 = 20.3 ± 0.43 µM).

scholarly journals Solvent-free synthesis of 1-amidoalkyl-2-naphthol and 3-amino-1-phenyl-1H benzo[f]chromene-2-carbonitrile derivatives by Fe3O4@enamine-B(OSO3H)2 as an efficient and novel heterogeneous magnetic nanostructure catalyst

2020 ◽  
Vol 22 (2) ◽  
pp. 9-19 ◽  
Author(s):  
Fangping Li ◽  
Jun Zhang ◽  
Longjiang Wang ◽  
Weijian Liu ◽  
Qahtan A. Yousif
Keyword(s):  
Reaction Times ◽  
Catalytic Amount ◽  
X Ray Diffraction ◽  
One Pot ◽  
X Ray ◽  
Magnetic Nanostructure ◽  
The One ◽  
High Yields ◽  
Green Procedure ◽  
Work Up

AbstractA green procedure for the one-pot three-component synthesis of 1-amidoalkyl-2-naphthol and 3-amino-1-phenyl-1H benzo[f]chromene-2-carbonitrile derivatives from the reaction of 2-naphtol, aldehydes, and malononitrile/acetamide in the presence of a catalytic amount of Fe3O4@enamine-B(OSO3H)2 as an efficient and novel heterogeneous magnetic nanostructure catalyst is described. The catalyst was characterized using Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), vibrating sample magnetometry (VSM), energy dispersive X-ray spectroscopy (EDX), and X-ray diffraction (XRD). These strategies possess some merits such as simple work-up method, easy preparation of the catalyst, short reaction times, good-to-high yields, and non-use of hazardous solvents during all steps of the reactions. Moreover, due to the magnetic nature of the catalyst, it was readily recovered by magnetic decantation and can be recycled at least six runs with no considerable decrease in catalytic activity.

scholarly journals Synthesis of 1-aryl-1-phenylpropenes using an alkylation-rearrangement-methylation-isomerization one-pot reaction sequence

2011 ◽  
Vol 9 (5) ◽  
pp. 904-909 ◽  
Author(s):  
Nenad Maraš ◽  
Franc Perdih ◽  
Marijan Kočevar
Keyword(s):  
Claisen Rearrangement ◽  
Structural Features ◽  
X Ray Diffraction ◽  
Reaction Sequence ◽  
One Pot ◽  
Double Bond Migration ◽  
X Ray ◽  
Crystalline Product ◽  
Tetramethylammonium Chloride ◽  
The One

Abstract(Z/E)-1-(2-Methoxyaryl)-1-phenylpropenes have been prepared in good yields by heating a mixture of a phenolic substrate, cinnamyl chloride, tetramethylammonium chloride and K2CO3 in polyethyleneglycol at 180°C. The one-pot synthesis proceeds through four discrete reaction steps: alkylation of the phenol with cinnamyl chloride, Claisen rearrangement, O-methylation and double-bond migration. The configuration of one crystalline product was determined using a single-crystal X-ray diffraction analysis. The thermodynamic and structural features of the products were evaluated using computational chemistry techniques.

scholarly journals Copper(II) Anchored on Amine-Functionalized MMT: A Highly Efficient Catalytic System for the One-Pot Synthesis of Bispyrano[2,3-c]pyrazole Derivatives

2021 ◽  
Vol 2021 ◽  
pp. 1-11
Author(s):  
Majid Ahmadzadeh ◽  
Masoud Sadeghi ◽  
Javad Safari
Keyword(s):  
Condensation Reaction ◽  
Significant Loss ◽  
Pyrazole Derivatives ◽  
X Ray Diffraction ◽  
Phenyl Hydrazine ◽  
One Pot ◽  
X Ray ◽  
Amine Functionalized ◽  
The One ◽  
High Yields

In this study, preparation of pyridine-2-carboimine copper complex immobilized on amine-functionalized nanoclay montmorillonite K10 was reported. The products were characterized by Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), and thermogravimetric analysis (TGA). The catalytic activity of this new nanocatalyst, as a natural, renewable, inexpensive, and heterogeneous catalyst, was very effective for the four-component condensation reaction of hydrazine hydrate (or phenyl hydrazine), malononitrile, β-ketoester, and terephthalaldehyde (or isophthalaldehyde) toward the synthesis of multisubstituted bispyrano[2,3-c]pyrazole derivatives. From the viewpoint of green chemistry, the advantages of this approach are accessibility, simplicity, and high yields synthesis. The catalyst was recycled and reused four times without significant loss of activity.

A highly efficient and green approach for the synthesis of pyrimido[4,5-b]quinolines using N,N-diethyl-N-sulfoethanaminium chloride

2021 ◽  
Vol 76 (2) ◽  
pp. 85-90
Author(s):  
Abdolkarim Zare ◽  
Manije Dianat
Keyword(s):  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Catalyst Amount ◽  
Green Protocol ◽  
Highly Efficient ◽  
Green Approach ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields

Abstract A highly efficient and green protocol for the synthesis of pyrimido[4,5-b]quinolines has been described. The one-pot multicomponent reaction of dimedone with arylaldehydes and 6-amino-1,3-dimethyluracil in the presence of N,N-diethyl-N-sulfoethanaminium chloride ([Et3N–SO3H][Cl]) as an ionic liquid (IL) catalyst under solvent-free conditions afforded the mentioned compounds in high yields and short reaction times. Our protocol is superior to many of the reported protocols in terms of two or more of these factors: the reaction times, yields, conditions (solvent-free versus usage of organic solvents), temperature and catalyst amount.

scholarly journals A Water-Soluble Copper-Immobilized Covalent Organic Framework Functioning as an “OFF–ON” Fluorescent Sensor for Amino Acids

2021 ◽  
Author(s):  
Lamiaa Reda Ahmed ◽  
Ahmed F. M. EL-Mahdy ◽  
Cheng-Tang Pan ◽  
Shiao-Wei Kuo
Keyword(s):  
Amino Acids ◽  
Fluorescent Sensor ◽  
Water Soluble ◽  
One Pot ◽  
Covalent Organic Framework ◽  
The One ◽  
Organic Framework

In this paper, we describe the construction of a new fluorescent hydroxyl- and hydrazone-based covalent organic framework (TFPB-DHTH COF) through the one-pot polycondensation of 1,3,5-tris(4-formylphenyl)benzene (TFPB) and 2,5-dihydroxyterephthalohydrazide (DHTH) under...

Rapid and Green One-Pot Synthesis of Novel 2-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-diones

2021 ◽  
Vol 18 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Zahra Ghahremany ◽  
Madieh Sadeghpour
Keyword(s):  
Aromatic Amines ◽  
Low Cost ◽  
Guanidine Hydrochloride ◽  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields ◽  
Work Up

: A green and efficient protocol was developed for the one-pot three-component synthesis of novel 2-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-dione derivatives by the reaction of 4-hydroxycoumarin, ninhydrin and aromatic amines in the presence of guanidine hydrochloride as an organocatalyst under solvent-free conditions. The present approach offers several advantages such as low cost, simple work-up, short reaction times, chromatography-free purification, high yields and greener conditions.

scholarly journals One-Pot Synthesis of Ru-Doped ZnO Oxides for Photodegradation of 4-Chlorophenol

2018 ◽  
Vol 2018 ◽  
pp. 1-12 ◽  
Author(s):  
Maria E. Manríquez ◽  
Luis Enrique Noreña ◽  
Jin An Wang ◽  
Lifang Chen ◽  
Jose Salmones ◽  
...  
Keyword(s):  
Band Gap ◽  
Mixed Oxides ◽  
Active Surface ◽  
Band Gap Energy ◽  
X Ray Diffraction ◽  
Electron Hole ◽  
One Pot ◽  
Notable Increase ◽  
Doped Zno ◽  
The One

The photocatalytic degradation of 4-chlorophenol in water using Ru-doped ZnO mixed oxides (0, 0.5, 1, and 3 wt% RuO2) synthesized by the one-pot homogeneous coprecipitation method is reported. ZnO with wurtzite structure was present in the mixed oxide as corroborated by Raman spectroscopy and X-ray diffraction analysis. All the samples showed nanorod morphological features. The presence of Ru6+/Ru4+ couples on ZnO modified the band gap of the mixed oxides and led to a shift of the band gap energy from 3.20 eV to 3.07 eV. Ru addition increased the surface area and significantly promoted the formation of active surface oxygen species such as hydroradicals evidenced by the fluorescence spectroscopy measurement. In the photodegradation of 4-chlorophenol solution under UV irradiation, a notable increase in photoactivity was obtained as the amount of RuO2 in the mixed oxides increased to 3 wt%. The charge transfer between Ru6+/Ru4+ couples and ZnO nanoparticles together with the formation of free radical oxidant species effectively inhibits electron-hole recombination rate, thus favoring the photodegradation of 4-chlorophenol.

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