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 ac dagger 2-azido-4-trifluoromethylpyrimidine was observed in the absence of solvent and in DMSO-d(6) 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-d(6) 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 ac dagger 2-azido-4-trifluoromethylpyri midine tautomeric rearrangement in DMSO-d(6) for 5-trifluoromethyltetrazolo[1,5-a]pyrimidine were determined using the exchange spectroscopy (EXSY) technique.

Cite: Nikolaenkova E.B. , Aleksandrova N.V. , Mamatyuk V.I. , Krivopalov V.P.
Synthesis and study of the azide-tetrazole tautomerism in 2-azido-4-(trifluoromethyl)-6-R-pyrimidines (R = H, 4-ClC6H4)
Russian Chemical Bulletin. 2018. V.67. N5. P.893-901. DOI: 10.1007/s11172-018-2154-z WOS Scopus РИНЦ

ArticleLinkType.TRANSLATED_TO_ORIGINAL: Николаенкова Е.Б. , Александрова Н.В. , Маматюк В.И. , Кривопалов В.П.
Синтез и исследование азидо-тетразольной таутомерии 2-азидо-4-(трифторметил)-6-R-пиримидинов (R = H, 4-ClC6H4)
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2018. №5. С.893-901. РИНЦ

Dates:

Published print:	May 1, 2018
Published online:	Aug 20, 2018

Identifiers:

Web of science	WOS:000442228300018
Scopus	2-s2.0-85051843398
Elibrary	35738502
OpenAlex	W2888073317

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