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Keywords = fluorinated pyrazolines

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15 pages, 3362 KB  
Article
(3+2)-Cycloadditions of Levoglucosenone (LGO) with Fluorinated Nitrile Imines Derived from Trifluoroacetonitrile: An Experimental and Computational Study
by Grzegorz Mlostoń, Katarzyna Urbaniak, Marcin Palusiak, Zbigniew J. Witczak and Ernst-Ulrich Würthwein
Molecules 2023, 28(21), 7348; https://doi.org/10.3390/molecules28217348 - 30 Oct 2023
Cited by 4 | Viewed by 2326
Abstract
The in situ-generated N-aryl nitrile imines derived from trifluoroacetonitrile smoothly undergo (3+2)-cycloadditions onto the enone fragment of the levoglucosenone molecule, yielding the corresponding, five-membered cycloadducts. In contrast to the ‘classic’ C(Ph),N(Ph) nitrile imine, reactions with fluorinated C(CF3 [...] Read more.
The in situ-generated N-aryl nitrile imines derived from trifluoroacetonitrile smoothly undergo (3+2)-cycloadditions onto the enone fragment of the levoglucosenone molecule, yielding the corresponding, five-membered cycloadducts. In contrast to the ‘classic’ C(Ph),N(Ph) nitrile imine, reactions with fluorinated C(CF3),N(Ar) analogues lead to stable pyrazolines in a chemo- and stereoselective manner. Based on the result of X-ray single crystal diffraction analysis, their structures were established as exo-cycloadducts with the location of the N-Ar terminus of the 1,3-dipole at the α-position of the enone moiety. The DFT computation demonstrated that the observed reaction pathway results from the strong dominance of kinetic control over thermodynamic control. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Synthesis)
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6 pages, 1052 KB  
Short Note
5-(4-Fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-1H-pyrazole
by Jasril Jasril, Neni Frimayanti, Yuana Nurulita, Adel Zamri, Ihsan Ikhtiarudin and Guntur Guntur
Molbank 2021, 2021(1), M1197; https://doi.org/10.3390/M1197 - 10 Mar 2021
Cited by 3 | Viewed by 5967
Abstract
A new fluorinated pyrazole, 5-(4-fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-1H-pyrazole was successfully synthesized via a two-step reaction. Firstly, the synthesis of pyrazoline was performed via one-pot three-component reaction under microwave irradiation. Secondly, the synthesis of pyrazole was performed via oxidative aromatization of pyrazoline under conventional heating. [...] Read more.
A new fluorinated pyrazole, 5-(4-fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-1H-pyrazole was successfully synthesized via a two-step reaction. Firstly, the synthesis of pyrazoline was performed via one-pot three-component reaction under microwave irradiation. Secondly, the synthesis of pyrazole was performed via oxidative aromatization of pyrazoline under conventional heating. The structure of the synthesized compound was confirmed by spectroscopic analysis, including FT-IR, HR-MS, 1D and 2D NMR analysis. Then, molecular docking study showed that the binding affinity of the synthesized compound to human estrogen alpha receptor (ERα) was close to 4-OHT as a native ligand. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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8 pages, 1476 KB  
Short Note
3-(3,4-Dimethoxyphenyl)-5-(2-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole
by Adel Zamri, Hilwan Y. Teruna, Sri Wulansari, Noval Herfindo, Neni Frimayanti and Ihsan Ikhtiarudin
Molbank 2019, 2019(4), M1088; https://doi.org/10.3390/M1088 - 12 Nov 2019
Cited by 7 | Viewed by 4105
Abstract
A new analogue of fluorinated pyrazoline (compound 1) has been synthesized via one-pot three-component reaction in a sealed-vessel reactor, Monowave 50. The structure of compound 1 has been established by spectroscopy analysis, including UV, FT-IR, HRMS, 1H and 13C NMR [...] Read more.
A new analogue of fluorinated pyrazoline (compound 1) has been synthesized via one-pot three-component reaction in a sealed-vessel reactor, Monowave 50. The structure of compound 1 has been established by spectroscopy analysis, including UV, FT-IR, HRMS, 1H and 13C NMR spectroscopy. Based on the in silico studies, this compound showed a good potential as an inhibitor for dengue virus type 2 (DEN2) NS2B/NS3 serine protease and can be used as a reference in the next design of an antidengue virus. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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13 pages, 1551 KB  
Article
Eco-Friendly Synthesis, Characterization and Biological Evaluation of Some Novel Pyrazolines Containing Thiazole Moiety as Potential Anticancer and Antimicrobial Agents
by Mastoura M. Edrees, Sraa Abu- Melha, Amirah M. Saad, Nabila A. Kheder, Sobhi M. Gomha and Zeinab A. Muhammad
Molecules 2018, 23(11), 2970; https://doi.org/10.3390/molecules23112970 - 14 Nov 2018
Cited by 64 | Viewed by 4956
Abstract
The one-pot synthesis of a series of pyrazoline derivatives containing the bioactive thiazole ring has been performed through a 1,3-dipolar cycloaddition reaction of N-thiocarbamoylpyrazoline and different hydrazonoyl halides or α-haloketones in the presence of DABCO (1,4-diazabicyclo[2.2.2] octane) as an eco-friendly catalyst using [...] Read more.
The one-pot synthesis of a series of pyrazoline derivatives containing the bioactive thiazole ring has been performed through a 1,3-dipolar cycloaddition reaction of N-thiocarbamoylpyrazoline and different hydrazonoyl halides or α-haloketones in the presence of DABCO (1,4-diazabicyclo[2.2.2] octane) as an eco-friendly catalyst using the solvent-drop grinding method. The structure of the synthesized compounds was elucidated using elemental and spectroscopic analyses (IR, NMR, and Mass). The activity of these compounds against human hepatocellular carcinoma cell line (HepG2) was tested and the results showed that the pyrazoline 11f, which has a fluorine substituent, is the most active. The antimicrobial activities of the newly synthesized compounds were determined against two fungi and four bacterial strains, and the results indicated that some of the newly synthesized pyrazolines are more potent than the standard drugs against test organisms. Full article
(This article belongs to the Collection Heterocyclic Compounds)
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7 pages, 1890 KB  
Communication
High Solid Fluorescence of a Pyrazoline Derivative through Hydrogen Bonding
by Liang Zhang, Jie Liu, Junkuo Gao, Feng Zhang and Liang Ding
Molecules 2017, 22(8), 1304; https://doi.org/10.3390/molecules22081304 - 4 Aug 2017
Cited by 14 | Viewed by 4768
Abstract
Pyrazoline and its derivatives often exhibit strong emissions in dilute solutions, but their emission intensity is often dramatically reduced in the solid state due to strong intermolecular interactions between neighboring molecules. In this report, we successfully synthesized a new pyrazoline 4-(3-(4-(decyloxy)phenyl)-1-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazol-5-yl)-N,N-diethylaniline (PPDPD), into [...] Read more.
Pyrazoline and its derivatives often exhibit strong emissions in dilute solutions, but their emission intensity is often dramatically reduced in the solid state due to strong intermolecular interactions between neighboring molecules. In this report, we successfully synthesized a new pyrazoline 4-(3-(4-(decyloxy)phenyl)-1-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazol-5-yl)-N,N-diethylaniline (PPDPD), into which seven fluorine (F) atoms were incorporated. In the solid state, PPDPD emits a strong blue light at λmax 430 nm with a fluorescence quantum yield of up to 41.3%. Single-crystal analysis showed the presence of intra/intermolecular C-H···F bonds that may impede molecular motion and block the non-radiative decay channel. Compound PPDPD therefore shows high emission efficiency in the solid state. Full article
(This article belongs to the Section Photochemistry)
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5 pages, 521 KB  
Short Note
5-(4-Fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-4,5-dihydro-1H-pyrazole
by Jasril Jasril, Adel Zamri, Ihsan Ikhtiarudin and Hilwan Y. Teruna
Molbank 2016, 2016(2), M891; https://doi.org/10.3390/M891 - 29 Mar 2016
Cited by 4 | Viewed by 4638
Abstract
A new fluorinated 1-naphtyl pyrazoline (4) has been successfully synthesized by reacting a fluorinated 1-naphtyl chalcone (3) with phenyl hydrazine under microwave irradiation. The structure of compound 4 was characterized by UV-Vis, FTIR, HRMS, 1D NMR and 2D NMR spectroscopies. Full article
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