Original scientific paper

Homologation and Intramolecular Cyclisation Readions in Aliphatic Deoxyuridine Analogues Series

Vinko Škarić ; Laboratory of Stereochemistry and Natural Products, »Ruder Boskovic« Institute, 41001 Zagreb, Croatia, Yugoslavia
Milan Jokić ; Laboratory of Stereochemistry and Natural Products, »Ruder Boskovic« Institute, 41001 Zagreb, Croatia, Yugoslavia

Abstract

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.

Keywords

Hrčak ID:

194248

URI

https://hrcak.srce.hr/194248

Publication date:

15.4.1983.

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