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Synthesis and study of the azide-tetrazole tautomerism in 2-azido-4-(trifluoromethyl)-6-R-pyrimidines (R = H, 4-ClC6H4). / Nikolaenkova, B.; Aleksandrova, N. V.; Mamatyuk, V. I. et al.

In: Russian Chemical Bulletin, Vol. 67, No. 5, 01.05.2018, p. 893-901.

Research output: Contribution to journal › Article › peer-review

Harvard

Nikolaenkova, B, Aleksandrova, NV, Mamatyuk, VI & Krivopalov, VP 2018, 'Synthesis and study of the azide-tetrazole tautomerism in 2-azido-4-(trifluoromethyl)-6-R-pyrimidines (R = H, 4-ClC6H4)', Russian Chemical Bulletin, vol. 67, no. 5, pp. 893-901. https://doi.org/10.1007/s11172-018-2154-z

APA

Nikolaenkova, B., Aleksandrova, N. V., Mamatyuk, V. I., & Krivopalov, V. P. (2018). Synthesis and study of the azide-tetrazole tautomerism in 2-azido-4-(trifluoromethyl)-6-R-pyrimidines (R = H, 4-ClC6H4). Russian Chemical Bulletin, 67(5), 893-901. https://doi.org/10.1007/s11172-018-2154-z

Vancouver

Nikolaenkova B, Aleksandrova NV, Mamatyuk VI, Krivopalov VP. Synthesis and study of the azide-tetrazole tautomerism in 2-azido-4-(trifluoromethyl)-6-R-pyrimidines (R = H, 4-ClC6H4). Russian Chemical Bulletin. 2018 May 1;67(5):893-901. doi: 10.1007/s11172-018-2154-z

Author

Nikolaenkova, B. ; Aleksandrova, N. V. ; Mamatyuk, V. I. et al. / Synthesis and study of the azide-tetrazole tautomerism in 2-azido-4-(trifluoromethyl)-6-R-pyrimidines (R = H, 4-ClC6H4). In: Russian Chemical Bulletin. 2018 ; Vol. 67, No. 5. pp. 893-901.

BibTeX

@article{0c4bfb3b5cd3473b9ec68b71d6f8aea9,
title = "Synthesis and study of the azide-tetrazole tautomerism in 2-azido-4-(trifluoromethyl)-6-R-pyrimidines (R = H, 4-ClC6H4)",
abstract = "Azide-tetrazole equilibrium in azidopyrimidines bearing trifluoromethyl group on the example of 2-azidopyrimidines has been studied. The latter were synthesized via nitrosation of 2-hydrazino-4-trifluoromethylpyrimidine and reaction of NaN3 with 4-trifluoromethyl-2- chloro-6-(4-chlorophenyl)pyrimidine. The tautomeric equilibrium 5-trifluoro methyl tetrazolo[1,5-a]pyrimidine ⇆ 2-azido-4-trifluoromethylpyrimidine was observed in the absence of solvent and in DMSO-d6 solution, whereas in CDCl3 only an azide form exists. For 2-azido- 4-trifluoromethyl-6-(4-chlorophenyl)pyrimidine, only an azide isomer was detected in CDCl3 solution, and in DMSO-d6 solution it is in equilibrium with 5-(trifluoromethyl)-7-(4-chlorophenyl) tetrazolo[1,5-a]pyrimidine (the tautomer ratio is 99 : 1). Thermodynamic and kinetic parameters of 5-trifluoromethyltetrazolo[1,5-a]pyrimidine ⇆ 2-azido-4-trifluoromethylpyri midine tautomeric rearrangement in DMSO-d6 for 5-trifluoromethyltetrazolo[1,5-a]pyrimidine were determined using the exchange spectroscopy (EXSY) technique.",
keywords = "2-azidopyrimidines, azidetetrazole tautomerism, equilibrium constants, exchange rate constants, exchange spectroscopy, NMR spectroscopy, tetrazolo[a]pyrimidines, trifluoromethylpyrimidines, 5-AMINOTETRAZOLE, azide-tetrazole tautomerism, 2-AZIDOPYRIMIDINES, SERIES, 4-AZIDOPYRIMIDINES, H-1-N-15, COUPLING-CONSTANTS, NMR, HETEROCYCLES, EQUILIBRIUM, ESTERS",
author = "B. Nikolaenkova and Aleksandrova, {N. V.} and Mamatyuk, {V. I.} and Krivopalov, {V. P.}",
note = "Publisher Copyright: {\textcopyright} 2018, Springer Science+Business Media, LLC, part of Springer Nature.",
year = "2018",
month = may,
day = "1",
doi = "10.1007/s11172-018-2154-z",
language = "English",
volume = "67",
pages = "893--901",
journal = "Russian Chemical Bulletin",
issn = "1066-5285",
publisher = "Springer Nature",
number = "5",

}

RIS

TY - JOUR

T1 - Synthesis and study of the azide-tetrazole tautomerism in 2-azido-4-(trifluoromethyl)-6-R-pyrimidines (R = H, 4-ClC6H4)

AU - Nikolaenkova, B.

AU - Aleksandrova, N. V.

AU - Mamatyuk, V. I.

AU - Krivopalov, V. P.

N1 - Publisher Copyright: © 2018, Springer Science+Business Media, LLC, part of Springer Nature.

PY - 2018/5/1

Y1 - 2018/5/1

N2 - Azide-tetrazole equilibrium in azidopyrimidines bearing trifluoromethyl group on the example of 2-azidopyrimidines has been studied. The latter were synthesized via nitrosation of 2-hydrazino-4-trifluoromethylpyrimidine and reaction of NaN3 with 4-trifluoromethyl-2- chloro-6-(4-chlorophenyl)pyrimidine. The tautomeric equilibrium 5-trifluoro methyl tetrazolo[1,5-a]pyrimidine ⇆ 2-azido-4-trifluoromethylpyrimidine was observed in the absence of solvent and in DMSO-d6 solution, whereas in CDCl3 only an azide form exists. For 2-azido- 4-trifluoromethyl-6-(4-chlorophenyl)pyrimidine, only an azide isomer was detected in CDCl3 solution, and in DMSO-d6 solution it is in equilibrium with 5-(trifluoromethyl)-7-(4-chlorophenyl) tetrazolo[1,5-a]pyrimidine (the tautomer ratio is 99 : 1). Thermodynamic and kinetic parameters of 5-trifluoromethyltetrazolo[1,5-a]pyrimidine ⇆ 2-azido-4-trifluoromethylpyri midine tautomeric rearrangement in DMSO-d6 for 5-trifluoromethyltetrazolo[1,5-a]pyrimidine were determined using the exchange spectroscopy (EXSY) technique.

AB - Azide-tetrazole equilibrium in azidopyrimidines bearing trifluoromethyl group on the example of 2-azidopyrimidines has been studied. The latter were synthesized via nitrosation of 2-hydrazino-4-trifluoromethylpyrimidine and reaction of NaN3 with 4-trifluoromethyl-2- chloro-6-(4-chlorophenyl)pyrimidine. The tautomeric equilibrium 5-trifluoro methyl tetrazolo[1,5-a]pyrimidine ⇆ 2-azido-4-trifluoromethylpyrimidine was observed in the absence of solvent and in DMSO-d6 solution, whereas in CDCl3 only an azide form exists. For 2-azido- 4-trifluoromethyl-6-(4-chlorophenyl)pyrimidine, only an azide isomer was detected in CDCl3 solution, and in DMSO-d6 solution it is in equilibrium with 5-(trifluoromethyl)-7-(4-chlorophenyl) tetrazolo[1,5-a]pyrimidine (the tautomer ratio is 99 : 1). Thermodynamic and kinetic parameters of 5-trifluoromethyltetrazolo[1,5-a]pyrimidine ⇆ 2-azido-4-trifluoromethylpyri midine tautomeric rearrangement in DMSO-d6 for 5-trifluoromethyltetrazolo[1,5-a]pyrimidine were determined using the exchange spectroscopy (EXSY) technique.

KW - 2-azidopyrimidines

KW - azidetetrazole tautomerism

KW - equilibrium constants

KW - exchange rate constants

KW - exchange spectroscopy

KW - NMR spectroscopy

KW - tetrazolo[a]pyrimidines

KW - trifluoromethylpyrimidines

KW - 5-AMINOTETRAZOLE

KW - azide-tetrazole tautomerism

KW - 2-AZIDOPYRIMIDINES

KW - SERIES

KW - 4-AZIDOPYRIMIDINES

KW - H-1-N-15

KW - COUPLING-CONSTANTS

KW - NMR

KW - HETEROCYCLES

KW - EQUILIBRIUM

KW - ESTERS

UR - http://www.scopus.com/inward/record.url?scp=85051843398&partnerID=8YFLogxK

U2 - 10.1007/s11172-018-2154-z

DO - 10.1007/s11172-018-2154-z

M3 - Article

AN - SCOPUS:85051843398

VL - 67

SP - 893

EP - 901

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

IS - 5

ER -

ID: 16083820