A convenient synthesis of 4(5)-(2-hydroxyaroyl)-5(4)-trifluoromethyl-1,2,3-triazoles from 2-trifluoromethylchromones and chromen-4-imines

Sosnovskikh, Vyacheslav Ya.; Usachev, Boris I.

doi:10.1070/mc2002v012n02abeh001562

Cited by 20 publications

(17 citation statements)

References 13 publications

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“…The 1 and 2 compounds were characterized by solution NMR ( 1 H, 13 C, 19 F) and electronic (UV-Vis) spectroscopy, and mass spectrometry. The solid state vibration behavior was studied by infrared (IR) absorption and Raman dispersion spectroscopy.…”

Section: Methodsmentioning

confidence: 99%

“…The gas phase geometry optimization of both molecules was performed by quantum chemical calculations. Additional theoretical studies were selected for calculating vibration mode frequencies (IR, Raman), UV-Vis transitions and NMR chemical shifts ( 1 H, 13 C, 19 F).…”

Section: Methodsmentioning

confidence: 99%

“…One of the most employed methods for the synthesis of chromones involves the reaction of ortho-hydroxyacetophenones with several acid anhydrides, followed by intra-molecular cyclization and subsequent dehydration [15][16][17][18]. The preparation of new 2-trifluoromethylchromones using the above method with trifluoroacetic ethyl ester has been reported by Sosnovskikh's group [19][20][21][22]. More recently, a new chemical pathway involving esterification and cyclization in one step using trifluoroacetic anhydride was developed in our laboratory [23].…”

Section: Introductionmentioning

confidence: 99%

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A detailed experimental and theoretical study of two novel substituted trifluoromethylchromones. The influence of the bulky bromine atom on the crystal packing

León

Echeverría

Piro

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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The new 3-methyl-2-trifluoromethylchromone (1) and 3-bromomethyl-2-trifluoromethylchromone (2) compounds were synthesized and characterized by vibrational (IR, Raman), UV-Vis and NMR ((1)H, (13)C and (19)F) spectroscopy and MS spectrometry. The crystal structures of 1 and 2 were determined by X-ray diffraction methods. Both compounds crystallize in the monoclinic P21/c space group with Z=4 molecules per unit cell. The structures were solved from 1423 (1) and 1856 (2) reflections with I>2σ (I) and refined by full-matrix least-squares to agreement R1-values of 0.0403 (1) and 0.0554 (2). Because of π-bonding delocalization, the organic molecular skeletons are planar and the molecular bonding structures can be described by formally single, double and resonant bonds. In 2, the CF3 group revealed a strong rotational disorder around the CCF3 bond, which could be explained in terms of four split positions with about uniform angular distribution. The vibrational, electronic and NMR, spectra were discussed and assigned with the assistance of DFT calculations.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A detailed experimental and theoretical study of two novel substituted trifluoromethylchromones. The influence of the bulky bromine atom on the crystal packing

León

Echeverría

Piro

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…S1-S21 in the supporting information). Triazoles 1-6 were synthesized using a metal-free domino reaction from aryl trifluoromethyl ketones and aryl azides in the presence of a base (DBU or triethylamine) in a 1:1:3 ratio (Sosnovskikh & Usachev, 2002;Usachev et al, 2011Usachev et al, , 2014. Triazole 7, which contains a hydroxy group, was prepared at room temperature using a catalytic amount of base DBU or trimethylamine from enolizable aryl trifluoromethyl ketones and aryl azides (Shashank et al, 2014) (Fig.…”

Section: Figurementioning

confidence: 99%

The structures of 1,4-diaryl-5-trifluoromethyl-1H-1,2,3-triazoles related to J147, a drug for treating Alzheimer's disease

et al. 2018

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J147 [N-(2,4-dimethylphenyl)-2,2,2-trifluoro-N'-(3-methoxybenzylidene)acetohydrazide] has recently been reported as a promising new drug for the treatment of Alzheimer's disease. The X-ray structures of seven new 1,4-diaryl-5-trifluoromethyl-1H-1,2,3-triazoles, namely 1-(3,4-dimethylphenyl)-4-phenyl-5-trifluoromethyl-1H-1,2,3-triazole (CHFN, 1), 1-(3,4-dimethylphenyl)-4-(3-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (CHFNO, 2), 1-(3,4-dimethylphenyl)-4-(4-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (CHFNO, 3), 1-(2,4-dimethylphenyl)-4-(4-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (CHFNO, 4), 1-[2,4-bis(trifluoromethyl)phenyl]-4-(3-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (CHFNO, 5), 1-(3,4-dimethoxyphenyl)-4-(3,4-dimethoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (CHFNO, 6) and 3-[4-(3,4-dimethoxyphenyl)-5-(trifluoromethyl)-1H-1,2,3-triazol-1-yl]phenol (CHFNO, 7), have been determined and compared to that of J147. B3LYP/6-311++G(d,p) calculations have been performed to determine the potential surface and molecular electrostatic potential (MEP) of J147, and to examine the correlation between hydrazone J147 and the 1,2,3-triazoles, both bearing a CF substituent. Using MEPs, it was found that the minimum-energy conformation of 4, which is nearly identical to its X-ray structure, is closely related to one of the J147 seven minima.

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“…The reactions of 2-trifl uoromethylchromones and 2-trifl uoromethyl-4H-chromen-4-imines with sodium azide in the presence of acetic acid gave ketone (or imine) derivatives of 5(4)-trifl uoromethyl-1,2,3-triazole 62 in high yields [ 67 ]. [ 68 ].…”

mentioning

confidence: 98%

Fluorinated Triazoles and Tetrazoles

Островский

Trifonov

2014

Fluorine in Heterocyclic Chemistry Volume 1

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A convenient synthesis of 4(5)-(2-hydroxyaroyl)-5(4)-trifluoromethyl-1,2,3-triazoles from 2-trifluoromethylchromones and chromen-4-imines

Cited by 20 publications

References 13 publications

A detailed experimental and theoretical study of two novel substituted trifluoromethylchromones. The influence of the bulky bromine atom on the crystal packing

A detailed experimental and theoretical study of two novel substituted trifluoromethylchromones. The influence of the bulky bromine atom on the crystal packing

The structures of 1,4-diaryl-5-trifluoromethyl-1H-1,2,3-triazoles related to J147, a drug for treating Alzheimer's disease

Fluorinated Triazoles and Tetrazoles

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