Promotional effect of ionic liquids in electrophilic fluorination of methylated uracils

Promotional effect of ionic liquids in electrophilic fluorination of methylated uracils Научная публикация

Журнал

RSC Advances
ISSN: 2046-2069

Вых. Данные

Год: 2016, Том: 6, Номер: 65, Страницы: 60556-60564 Страниц : DOI: 10.1039/c6ra10850d

Авторы

Borodkin Gennady I. ^1,2 , Elanov Innokenty R. ¹ , Gatilov Yury V. ^1,2 , Shubin Vyacheslav G. ¹

Организации

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Acad Lavrentev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogov St 2, Novosibirsk 630090, Russia

A novel efficient protocol has been developed for fluorination of methylated uracils involving a stoichiometric amount of ionic liquid (IL) in alcohols. The fluorination of 6-methyluracil and 1,3,6-trimethyluracil has been carried out using the electrophilic fluorinating reagent Selectfluor T (F-TEDA-BF4) in MeOH and EtOH solvents with the formation of 5-fluoro-6-methyluracil, 5-fluoro-1,3,6-trimethyluracil as well as alpha-fluoromethoxy- and alpha-fluoroethoxy ethers of difluorodihydrouracils as the main products. The use of a stoichiometric amount of ionic liquid as an additive results in acceleration of the reaction. It has been found that the effect of the anion of the IL on the rate of the reaction is more pronounced compared to that of the cation, the effectiveness of the anions decreasing in the following order: [HSO4-] > [OTf-] similar to [NTf2-] > [BF4-] > [PF6-]. The influence of metal carbonates on the yields of fluorouracils has also been evaluated.

Borodkin G.I. , Elanov I.R. , Gatilov Y.V. , Shubin V.G.
Promotional effect of ionic liquids in electrophilic fluorination of methylated uracils
RSC Advances. 2016. V.6. N65. P.60556-60564. DOI: 10.1039/c6ra10850d WOS Scopus

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