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Homologation and Intramolecular Cyclisation Reactions in Aliphatic Deoxyuridine Analogues Series (CROSBI ID 168190)

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Škarić, Vinko ; Jokić, Milan Homologation and Intramolecular Cyclisation Reactions in Aliphatic Deoxyuridine Analogues Series // Croatica chemica acta, 56 (1983), 1; 125-139

Podaci o odgovornosti

Škarić, Vinko ; Jokić, Milan

engleski

Homologation and Intramolecular Cyclisation Reactions in Aliphatic Deoxyuridine Analogues Series

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.

aliphatic dihydroxypropil deoxyuridine analogues

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Podaci o izdanju

56 (1)

1983.

125-139

objavljeno

0011-1643

Povezanost rada

Kemija

Poveznice