Synthesis and properties of 5-aryl-3-diazo-3H-pyrazoles and 3-aryl-1H-pyrazole-5-diazonium salts. Preparation and cytolytic activity studies of 2-arylpyrazolo-[5,1-c][1,2,4]benzotriazines

Alekseeva, D. L.; Rakhimova, Viktoriya Yu.; Minin, Artem S.; Белоусова, Анна В.; Садчикова, Е. В.

doi:10.1007/s10593-019-02406-8

Cited by 6 publications

(2 citation statements)

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“…The reaction of azole diazonium salts 1 [ 24 ] with heterocyclic enamines 2 and 3 leads to azolo[5,1- c ][1,2,4]triazines 4 and 5 [ 25 ] ( Scheme 1 ). Analogous azolotriazines were synthesized previously by using enamines, obtained from various secondary linear N , N -dialkylamines, and cyclic amines—pyrrolidine, piperidine, morpholine [ 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 ].…”

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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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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“…In the current work, we studied the reaction of 4-substituted 5-diazoazoles (diazopyrazole and diazoimidazoles) with N,Ndimethyl-2-(1,2,3-thiadiazol-5-yl)ethen-1-amines to enlarge the scope of the azolotriazines. Since we previously showed 21,22 that spectroscopy data are a convenient tool for differentiation between the two active diazo components, 23 we applied NMR and IR spectroscopy to confirm the structure of the diazo component and monitor the reaction pathways and intermediates formation.…”

Section: Introductionmentioning

confidence: 99%

Non-aromatic azolo[5,1-c][1,2,4]triazines: a pot, atom and step economic (PASE) synthesis, mechanistic insight and fluorescence properties

et al. 2022

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Bicyclic 5-6 Systems With One Bridgehead (Ring Junction) Nitrogen Atom: Three Extra Heteroatoms 1:2

David¹

2022

Comprehensive Heterocyclic Chemistry IV

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Synthesis and properties of 5-aryl-3-diazo-3H-pyrazoles and 3-aryl-1H-pyrazole-5-diazonium salts. Preparation and cytolytic activity studies of 2-arylpyrazolo-[5,1-c][1,2,4]benzotriazines

Cited by 6 publications

References 15 publications

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

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

Non-aromatic azolo[5,1-c][1,2,4]triazines: a pot, atom and step economic (PASE) synthesis, mechanistic insight and fluorescence properties

Bicyclic 5-6 Systems With One Bridgehead (Ring Junction) Nitrogen Atom: Three Extra Heteroatoms 1:2

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