Naslov
Homologation and Intramolecular Cyclisation Reactions in Aliphatic Deoxyuridine Analogues Series

Autori
Škarić, Vinko ; Jokić, Milan

Izvornik
Croatica Chemica Acta (0011-1643) 56 (1983), 1; 125-139

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
aliphatic dihydroxypropil deoxyuridine analogues

Sažetak
The synthesis and study of structural, stereochemical and biochemical features of the dihydroxyalkyl nucleosides analogues were described especially in their relations to naturally occuring nucleosides. The cyanation of 1-(2, 3-epoxypropyl)uracil (VIII), followed by the ethainolysis of the resulting 3'-cyano compound VI (R=H)' to 3'-ethoxycarbonyl derivative VII (R=H), led to the synthesis of 1~(2, 4-dihyd11oxybutyl)uracil (II, R and R1=H). The oxidation of 1-allylumcil by KMn04 gave 1-(2, 3-dihydroxypropyl)uracil (I, R=H) (Scheme 1). The intramolecular transformations of suitably activated I (R=H) were studied and the structures of the resulting 2, 3-dihydro- 2-hydroxymethy l-7H-oxazolo [3, 2-a] pyrimidin-7-one (X), 1 (2, 3- -d:ihydroxypropy 1)-2-0-methy luracil (XI) aind their mesyl, azido, and trityl derivatives are descibed (Scheme 2). In addition the 2-azidomethyl- (XXI) was converted into 2--aminomethyl- (XXUI) 2, 3-dihydro-7H-oxazolo [3, 2-a] pyrimidin-7-one.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA