Synthesis of isomerically pure 3-(5-trifluoromethyl-1,2,3-triazol-4-yl)cinnamic acid derivatives via the reaction of 4-aryl-6-trifluoromethyl-2-pyrones with sodium azide

Usachev, Sergey А.; Usachev, Boris I.; Eltsov, Oleg S.; Sosnovskikh, Vyacheslav Ya.

doi:10.1016/j.tet.2014.09.093

Cited by 11 publications

(6 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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

View full text Add to dashboard Cite

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.

show abstract

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

View full text Add to dashboard Cite

show abstract

“…The reaction of pyrone 5a with ammonia in ethanol in an autoclave at 120 °C for 10 h led to the formation of pyridone 7 in 70% yield. The ring-opening transformation of pyrone 5a with sodium azide [ 43 ] in DMSO afforded triazole 8 in 55% yield. Phenylhydrazine reacted with pyrone 5a regioselectively attacking with the amino group at the C-2 and C-4 positions to give pyrazole 9 .…”

Section: Resultsmentioning

confidence: 99%

2-Aryl-6-Polyfluoroalkyl-4-Pyrones as Promising RF-Building-Blocks: Synthesis and Application for Construction of Fluorinated Azaheterocycles

et al. 2021

Self Cite

View full text Add to dashboard Cite

A convenient and general method for the direct synthesis of 2-aryl-6-(trifluoromethyl)-4-pyrones and 2-aryl-5-bromo-6-(trifluoromethyl)-4-pyrones has been developed on the basis of one-pot oxidative cyclization of (E)-6-aryl-1,1,1-trifluorohex-5-ene-2,4-diones via a bromination/dehydrobromination approach. This strategy was also applied for the preparation of 2-phenyl-6-polyfluoroalkyl-4-pyrones and their 5-bromo derivatives. Conditions of chemoselective enediones bromination were found and the key intermediates of the cyclization of bromo-derivatives to 4-pyrones were characterized. Synthetic application of the prepared 4-pyrones has been demonstrated for the construction of biologically important CF3-bearing azaheterocycles, such as pyrazoles, pyridones, and triazoles.

show abstract

“…The title compounds were synthesized from the respective 2-trifluoromethylchromones (TFMC) 12,13 and 6-nitro-2-trifluoromethylchromone. 35 TFMC were prepared following the one-pot procedure reported by Henao Castañeda.…”

Section: Synthesismentioning

confidence: 99%

“…10 Vicinal triazoles without substitution on the nitrogen atom can be obtained by reacting sodium azide with  and  pyrones. 12,13 This synthetic route is simple and allows the construction of new heterocyclic structures substituted with trifluoromethyl groups possessing interesting properties. For this purpose, chromone is used as a source of  pyrone, with the advantage that trifluorochromones are obtained in a one-step simple way.…”

Section: Introductionmentioning

confidence: 99%

Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives

et al. 2020

View full text Add to dashboard Cite

show abstract

Synthesis of isomerically pure 3-(5-trifluoromethyl-1,2,3-triazol-4-yl)cinnamic acid derivatives via the reaction of 4-aryl-6-trifluoromethyl-2-pyrones with sodium azide

Cited by 11 publications

References 48 publications

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

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

2-Aryl-6-Polyfluoroalkyl-4-Pyrones as Promising RF-Building-Blocks: Synthesis and Application for Construction of Fluorinated Azaheterocycles

Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives

Contact Info

Product

Resources

About