Original scientific paper

Anti-Cyclisation Reactions of Enantiomeric 1-(2,3-Dihydroxypropyl)uracil Derivatives

V. Škarić ; Laboratory of Stereochemistry and Naturat Products, »Rudjer Bošković« Institute, 41001Zagreb, Croatia, Yugoslavia
B. Kašnar ; Laboratory of Stereochemistry and Naturat Products, »Rudjer Bošković« Institute, 41001Zagreb, Croatia, Yugoslavia

Abstract

The synthesis and enantiomeric features of 2-hydroxymethyl-
-tetrahydro-oxazolo[3,2-c]pyrimidine-5,7-(4H,6H)-diones (V) are.
described. The diazomethane methylation of these bicyclic compounds
afforded 2-hydroxymethyl-6-methyl-tetrahydro-oxazolo-
-[3,2-c]pyrimidine-5,7-(4H,6H)-diones (R)-(XXII) and (S)-(XXII),
respectively. For the synthesis of (R)-V and (S)-V the respective
5-bromo-1-(2,3-dihydroxypropyl)uracil (R)-(XVII) and (S)-(XVII)
were treated with KCN in DMF. The intermediate (R,S)-6-cyano-
-1-(2,3-dihydroxypropyl)uracil (XI) was shown to undergo the
anti-cyclisation yielding (R,S)-V if heated in DMSO at 40°c.

Keywords

Hrčak ID:

178047

URI

https://hrcak.srce.hr/178047

Publication date:

6.3.1986.

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