Synthesis of 2‐Aryl‐1,2,3‐triazoles by Oxidative Cyclization of 2‐(Arylazo)ethene‐1,1‐diamines: A One‐Pot Approach

Gavlik, Kseniya D.; Lesogorova, Svetlana G.; Sukhorukova, Ekaterina S.; Subbotina, Julia O.; Слепухин, П. А.; Benassi, Enrico; Belskaya, Nataliya P.

doi:10.1002/ejoc.201600256

Cited by 23 publications

(23 citation statements)

References 54 publications

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“…In the solid state, molecule 1b is expected to be symmetrically H-bonded in a cyclic dimer form through the –COOH group, as in related molecules [ 17 ] with carboxylic groups [ 21 ]. Thus, the dimeric structure of 1b was optimized, as plotted in Figure 2 .…”

Section: Resultsmentioning

confidence: 99%

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Study of the Molecular Architectures of 2-(4-Chlorophenyl)-5-(pyrrolidin-1-yl)-2H-1,2,3-triazole-4-carboxylic Acid Using Their Vibrational Spectra, Quantum Chemical Calculations and Molecular Docking with MMP-2 Receptor

Palafox,

Belskaya,

Kostova

2023

Pharmaceutics

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1,2,3-triazole skeleton is a valuable building block for the discovery of new promising anticancer agents. In the present work, the molecular structure of the synthesized anticancer drug 2-(4-chlorophenyl)-5-(pyrrolidin-1-yl)-2H-1,2,3-triazole-4-carboxylic acid (1b) and its anionic form (2b) was characterized by means of the B3LYP, M06-2X and MP2 quantum chemical methods, optimizing their monomer, cyclic dimer and stacking forms using the Gaussian16 program package. The molecular structure was found to be slightly out of plane. The good agreement between the IR and Raman bands experimentally observed in the solid state with those calculated theoretically confirms the synthesized structures. All of the bands were accurately assigned according to functional calculations (DFT) in the monomer and dimer forms, together with the polynomic scaling equation procedure (PSE). Therefore, the effect of the substituents on the triazole ring and the effect of the chlorine atom on the molecular structure and on the vibrational spectra were evaluated through comparison with its non-substituted form. Through molecular docking calculations, it was evaluated as to how molecule 1b interacts with few amino acids of the MMP-2 metalloproteinase receptor, using Sybyl-X 2.0 software. Thus, the relevance of triazole scaffolds in established hydrogen bond-type interactions was demonstrated.

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Section: Resultsmentioning

confidence: 99%

“…Molecules 1b and 2b were obtained by means of the alkaline hydrolysis of 2-(4-chlorophenyl)-5-(pyrrolidin-1-yl)-2 H -1,2,3-triazole-4-carbonitrile according to previously developed procedures [ 17 , 21 ]. 1,2,3-triazole-containing molecules form a white powder at room temperature.…”

Section: Methodsmentioning

confidence: 99%

Study of the Molecular Architectures of 2-(4-Chlorophenyl)-5-(pyrrolidin-1-yl)-2H-1,2,3-triazole-4-carboxylic Acid Using Their Vibrational Spectra, Quantum Chemical Calculations and Molecular Docking with MMP-2 Receptor

Palafox,

Belskaya,

Kostova

2023

Pharmaceutics

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“…Triazoles 1a and 2a were obtained by alkaline hydrolysis of 2-(4-methoxyphenyl)-5-(pyrrolidin-1-yl)-2 H -1,2,3-triazole-4-carbonitrile according to previously developed procedures [ 24 , 25 ]. The IR spectra in the powder form were recorded in the 400–4000 cm –1 range on a Brüker IFS-66 FTIR spectrometer equipped with a Globar source, Ge/KBr beam splitter and a TGS detector.…”

Section: Methodsmentioning

confidence: 99%

Peculiarities of the Spatial and Electronic Structure of 2-Aryl-1,2,3-Triazol-5-Carboxylic Acids and Their Salts on the Basis of Spectral Studies and DFT Calculations

Alcolea Palafox,

Belskaya,

Kostova

2023

IJMS

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The molecular structure and vibrational spectra of six 1,2,3-triazoles-containing molecules with possible anticancer activity were investigated. For two of them, the optimized geometry was determined in the monomer, cyclic dimer and stacking forms using the B3LYP, M06-2X and MP2 methods implemented in the GAUSSIAN-16 program package. The effect of the para-substitution on the aryl ring was evaluated based on changes in the molecular structure and atomic charge distribution of the triazole ring. An increment in the positive N4 charge was linearly related to a decrease in both the aryl ring and the carboxylic group rotation, with respect to the triazole ring, and by contrast, to an increment in the pyrrolidine ring rotation. Anionic formation had a larger effect on the triazole ring structure than the electronic nature of the different substituents on the aryl ring. Several relationships were obtained that could facilitate the selection of substituents on the triazole ring for their further synthesis. The observed IR and Raman bands in the solid state of two of these compounds were accurately assigned according to monomer and dimer form calculations, together with the polynomic scaling equation procedure (PSE). The large red-shift of the C=O stretching mode indicates that strong H-bonds in the dimer form appear in the solid state through this group.

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“…Only a few 1,2,4-triazine derivatives have been employed as building blocks for organic photoactive materials, particularly organic light-emitting diodes [ 12 , 13 , 14 , 15 , 16 , 17 , 18 ]. However, their closed nitrogen congeners (such as triazoles, pyrimidines, and s -triazines) are an inexhaustible source of numerous photoactive substances for various applications in optoelectronics and luminescent materials [ 19 , 20 , 21 , 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties

et al. 2023

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New fluorescent dyes containing an assembled 1,4-dihydroazolo[5,1-c][1,2,4]triazine (DAT) core and an isoxazole ring were synthesized through a reaction between diazopyrazole or diazoimidazoles and isoxazolyl-derived enamines in mild conditions. The photophysical characteristics (maxima absorption and emission, Stokes shifts, fluorescent quantum yields, and fluorescence lifetimes) of the new fluorophores were obtained. The prepared DATs demonstrated emission maxima ranging within 433–487 nm, quantum yields within 6.1–33.3%, and a large Stokes shift. The photophysical characteristics of representative DAT examples were studied in ten different solvents. Specific (hydrogen bonds) and non-specific (dipole–dipole) intermolecular and intramolecular interactions were analyzed using XRD data and spectral experiments. Solvatochromism was analyzed using Lippert–Mataga and Dimroth–Reichardt plots, revealing the relationship between the DAT structure and the nature of solute–solvent interactions. The significant advantages of DATs are the fluorescence of their powders (QY up to 98.7%). DAT-NMe2 10 expressed bright aggregation-induced emission (AIE) behavior in DMSO and THF as the water content increased. The numerous possible variations of the structures of the heterocycles included in the DATs, as well as substituents, create excellent prospects for adjusting their photophysical and physicochemical properties.

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Synthesis of 2‐Aryl‐1,2,3‐triazoles by Oxidative Cyclization of 2‐(Arylazo)ethene‐1,1‐diamines: A One‐Pot Approach

Cited by 23 publications

References 54 publications

Study of the Molecular Architectures of 2-(4-Chlorophenyl)-5-(pyrrolidin-1-yl)-2H-1,2,3-triazole-4-carboxylic Acid Using Their Vibrational Spectra, Quantum Chemical Calculations and Molecular Docking with MMP-2 Receptor

Study of the Molecular Architectures of 2-(4-Chlorophenyl)-5-(pyrrolidin-1-yl)-2H-1,2,3-triazole-4-carboxylic Acid Using Their Vibrational Spectra, Quantum Chemical Calculations and Molecular Docking with MMP-2 Receptor

Peculiarities of the Spatial and Electronic Structure of 2-Aryl-1,2,3-Triazol-5-Carboxylic Acids and Their Salts on the Basis of Spectral Studies and DFT Calculations

Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties

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