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

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

Журнал

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Вых. Данные

Год: 2018, Том: 67, Номер: 5, Страницы: 893-901 Страниц : 9 DOI: 10.1007/s11172-018-2154-z

Ключевые слова

2-azidopyrimidines; tetrazolo[a]pyrimidines; trifluoromethylpyrimidines; azide-tetrazole tautomerism; equilibrium constants; exchange rate constants; NMR spectroscopy; exchange spectroscopy

Авторы

Nikolaenkova E.B. ¹ , Aleksandrova N.V. ¹ , Mamatyuk V.I. ^1,2 , Krivopalov V.P. ¹

Организации

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Inst Organ Chem, 9 Prosp Akad Lavrentieva, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, 2 Ul Pirogova, Novosibirsk 630090, Russia

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.

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

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

Опубликована в печати:	1 мая 2018 г.
Опубликована online:	20 авг. 2018 г.

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