scholarly journals Diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate

Molbank ◽  
10.3390/m1167 ◽  
2020 ◽  
Vol 2020 (4) ◽  
pp. M1167
Author(s):  
Serigne Abdou Khadir Fall ◽  
Saïd Achamlale ◽  
Younas Aouine ◽  
Asmae Nakkabi ◽  
Hassane Faraj ◽  
...  
Keyword(s):  
Infrared Spectroscopy ◽  
Elemental Analysis ◽  
Cycloaddition Reaction ◽  
2D Nmr ◽  
Solvent Mixture ◽  
Sodium Ascorbate ◽  
Dipolar Cycloaddition ◽  
Sulfate Pentahydrate ◽  
Copper Sulfate Pentahydrate

The title compound, diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate, was synthesized with excellent yield and high regioselectivity through 1,3-dipolar cycloaddition reaction between the α-azido diethyl amino methylphosphonate and the heterocyclic alkyne, 9-(prop-2-yn-1-yl)-9H-carbazole. The cyclization reaction by “click chemistry” was carried out in a water/ethanol solvent mixture (50/50), in the presence of copper sulfate pentahydrate and catalytic sodium ascorbate. The characterization of the structure of the resulting 1,4-regioisomer was performed by 1D and 2D-NMR experiments, infrared spectroscopy, and elemental analysis.

scholarly journals Synthesis and Characterization of the Structure of Diethyl [(4-{(1H-Benzo[d]Imidazol-1-yl)Methyl}-1H-1,2,3-Triazol-1-yl)(Benzamido)Methyl]Phosphonate Using 1D and 2D NMR Experiments

2021 ◽  
Vol 2 (1) ◽  
pp. 1-7
Author(s):  
F. Serigne Abdou Khadir ◽  
S. Boukhssas ◽  
S. Achamlale ◽  
Y. Aouine ◽  
A. Nakkabi ◽  
...  
Keyword(s):  
Click Chemistry ◽  
Cycloaddition Reaction ◽  
2D Nmr ◽  
Sodium Ascorbate ◽  
Synthesis And Characterization ◽  
Two Dimensional ◽  
Ethanol Mixture ◽  
Solvent Water ◽  
Pure Product

The biheterocyclic derivative of the phosphonic glycine analogue is prepared selectively by reaction between the α-azidoamino diethyl methylphosphonate and the 1-(prop-2-yn-1-yl)-1H-benzo[d]imidazole. The dipolar -1,3 cycloaddition reaction using Click Chemistry was carried out in a solvent water/ethanol mixture in a ratio of 1:1. Copper sulphate pentahydrate and sodium ascorbate are used in the reaction in catalytic amounts. The compound [diethyl [{4-[(1H-benzo[d]imidazol-1-yl)methyl]-1H-1,2,3-triazol-1-yl}(benzamido) methyl] phosphonate was isolated pure as a white powder, after chromatography on a silica gel column (ethyl acetate/hexane acetate: 1/1). The yield of pure product is 90%, after recrystallization in an ether/hexane mixture. The structure of the -1,4 isomer is attributed to the compound obtained by means of 1D and 2D NMR and based on data from the literature concerning the cycloaddition reaction via Click Chemistry. Two-dimensional NMR spectroscopy played a major role. The analysis of the different correlations between adjacent hydrogens and carbons, and also between hydrogens and distant carbons, confirmed the proposed structure.

scholarly journals Synthesis and Characterization of a Novel Biheterocyclic -amino Acid Precursor of the Triazole-Tetrazole Type, via the Copper (I) Catalyzed Alkyne-Azide Cycloaddition Reaction (CuAAC)

2021 ◽  
Vol 2 (2) ◽  
pp. 7-15
Author(s):  
Khadim Dioukhane ◽  
Younas Aouine ◽  
Salaheddine Boukhssas ◽  
Asmae Nakkabi ◽  
Hassane Faraj ◽  
...  
Keyword(s):  
Amino Acid ◽  
Cycloaddition Reaction ◽  
Sodium Ascorbate ◽  
Dipolar Cycloaddition ◽  
Resonance Spectroscopy ◽  
Compound A ◽  
Amino Acid Precursor ◽  
Acid Precursor

In this paper, we describe the regioselective synthesis of a novel tri-heterocyclic compound, a biheterocyclic amino acid precursor, derived from both triazole and tetrazole. The key step of our synthesis approach was the Huigsen 1,3-dipolar cycloaddition reaction, catalyzed by the copper (I) formed in situ by reduction of Cu(II) salts (CuSO4), 5H2O) by sodium ascorbate, and using as dipole the oxazoline azide derivative 4-(azidomethyl)-4-ethyl-2-phenyl-4,5-dihydrooxazole (4) and as dipolarophile 5-(4-methoxyphenyl)-2-(prop-2-yn-1-yl)-2H-tetrazole (3).  The Cu(I) catalysis allowed us to carry out the cycloaddition at room temperature during a reaction time of only 8 hours and also to selectively obtain the 1,4-regioisomer; one of the two possible isomers, with a yield of 90% after chromatography on a silica gel column (ether/hexane: 1/2), and recrystallization in an ether/acetone mixture. The desired compound, 4-ethyl-4-((4-((5-(4-methoxyphenyl)-2H-tetrazol-2-yl)methyl)-1H-1,2,3-triazol-1-yl)methyl)-2-phenyl-4,5-dihydrooxazole (5) was analyzed by 1D magnetic resonance spectroscopy (1H, 13C), and characterized physico-chemically by mass spectrometry and elemental analysis.

New Pyrrolo[1,2-b]pyridazine Derivatives by 1,3-Dipolar Cycloaddition of Mesoionic Oxazolopyridazinone

2008 ◽  
Vol 59 (11) ◽  
Author(s):  
Miron Teodor Caproiu ◽  
Florea Dumitrascu ◽  
Mino R. Caira
Keyword(s):  
Nmr Spectroscopy ◽  
Elemental Analysis ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Pyridazine Derivatives ◽  
New Compounds

New pyrrolo[1,2-b]pyridazine derivatives 8a-f were synthesized by 1,3-dipolar cycloaddition reaction between mesoionic 1,3-oxazolo[3,2-b]pyridazinium-2-oxides and diethyl or diisopropyl acetylenedicarboxylate as alkyne dipolarophiles. The structures of the new compounds were assigned by elemental analysis and NMR spectroscopy.

Simple, stepwise and alternative syntheses of indolyl triazoles via Huisgen,s 1, 3-dipolar cycloaddition reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Ch. Venkata Ramana Reddy ◽  
G. Ganga Reddy
Keyword(s):  
Reaction Time ◽  
Addition Reaction ◽  
Click Reaction ◽  
Cycloaddition Reaction ◽  
Sodium Ascorbate ◽  
Dipolar Cycloaddition ◽  
Spectroscopic Methods ◽  
Aryl Azides ◽  
Simple Processing ◽  
High Yields

: A series of new 2-((1-((1-(4-methoxy-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl)1H-indol-3-yl)me thylene)malononitrile derivatives were synthesized by the 1,3 dipolar cyclo addition reaction (click reaction) of 2-((1-(prop-2-yn-1-yl)-1H-indol-3-yl)methylene)malononitrile with different aryl azides in the presence of sodium ascorbate and copper sulphate in good yields. The advantages of this method are efficient, clean, high yields, easy workup procedures and shorter reaction time. These reactions are very facile giving products by simple processing that does not require purification by column chromatography. All the newly synthesized compounds were confirmed by spectroscopic methods.

Synthesis and Structural Elucidation of Novel Spiropyrazolines Precursors to Spiro-gem-dimethylcyclopropanes

2005 ◽  
Vol 2005 (8) ◽  
pp. 498-501
Author(s):  
Karim Ben Ali ◽  
Najeh Boukamcha ◽  
Abdelkader Khemiss ◽  
Marie-Thérèse Martin
Keyword(s):  
Cycloaddition Reaction ◽  
2D Nmr ◽  
Structural Elucidation ◽  
Dipolar Cycloaddition

1,3-dipolar cycloaddition reaction of 2-diazopropane (DAP) 1 with 2-arylidene-1-tetralone 2a–b led exclusively to spiro-Δ1-pyrazolines 3a–b. When 4-methyl-2-arylidene-1-tetralones 2c–d was used as starting dipolarophile a mixture of diastereiosomeric cycloadducts 4a–b and 5a–b was obtained. The photochemical nitrogen-extrusion studied for spiropyrazolines 3a–b and 4a–b led stereospecifically to spiro-gem-dimethylcyclopropanes. In all cases, the reaction regiochemistry and stereochemistry was discussed on the basis of 2D-NMR experiments.

Synthesis and In Vitro Anti-Ulcer Effect of Triazolo-Methyl Tetrahydrobenzofuran Oxime Ether Derivatives

2013 ◽  
Vol 746 ◽  
pp. 35-39 ◽  
Author(s):  
Hu Biao Fang ◽  
Lei Jin ◽  
Cheng Qiao Cao ◽  
Hua Jun Luo ◽  
Nian Yu Huang
Keyword(s):  
Elemental Analysis ◽  
Cycloaddition Reaction ◽  
Inhibitory Effect ◽  
Dipolar Cycloaddition ◽  
Reaction Sequence ◽  
Oxime Ether ◽  
Esi Ms ◽  
Mild Conditions ◽  
Activity Evaluation

The triazolo-methyl tetrahydrobenzofuran oxime ether isomers were prepared through Cu (II)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction in a high-yielding three-step reaction sequence under mild conditions. All of the intermediates and target compounds were characterized by NMR, IR, ESI-MS and elemental analysis. Thein vitroanti-ulcer activity evaluation indicated the (Z)-oxime isomer of triazolo-methyl tetrahydrobenzofuran oxime ether exhibited most potent H+/K+-ATPase inhibitory effect with the IC50˰̵̱̼͆ͅ˰̶̿˰̅˾́̅˰μ̝˾ These compounds could be potentially used as anti-ulcer agents for the treatment of acid related diseases.

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