Naslov
Efficient Synthetic Routes for the Preparation of the Oxazolo[3, 2-c]Pyrimidines

Autori
Matić, Josipa ; Ban, Željka ; Saftić, Dijana ; Žinić, Biserka

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Book of abstracts ; P-D4-080 / - Istanbul, 2014, P-D4-080-P-D4-080

Skup
5th EUCHEMS Chemistry Congress- 2014

Mjesto i datum
Istanbul, Turska, 31.08.2014. - 04.09.2014

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Cyclonucleosides ; Intramolecular Anticyclisation

Sažetak
Cyclonucleosides, the compounds that have an extra linkage between the nucleobase and sugar, are an interesting class of compounds since they can be used as intermediates in the synthesis of 2-, 4-, and 6-substituted pyrimidine nucleosides or the sugar-substituted derivatives. The O6, 2¢-cyclonucleosides can be readily prepared by treatment of arabinosyl-5-bromopyrimidines with sodium methoxide in methanol by an intramolecular anti-cyclisation. However, the attempted cyclisation reactions of dihydroxypropyl 5-bromo-3-methyl-derivative 1 and 5-bromo derivative 3 under the same conditions failed. We found that treatment of 5-bromo-3-methyl derivative 1 with DBU/DMF affected its anti-cyclisation into 2 in 95% yield. On the contrary, the unprotected derivative 3 was unaffected under the same conditions. Using KCN/DMF the anti-cyclisation of 3 into 4 was observed in 70% yield. The mechanism of these anti-cyclisation reactions will be discussed on the basis of different intermediates isolated in these reactions.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA