Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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. и др.
в: Russian Chemical Bulletin, Том 67, № 5, 01.05.2018, стр. 893-901.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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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