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Unsaturated Sugars: Syntheses and Applications. A Special Issue in Honour of Professor Kalpattu Kuppuswamy Balsubramanian
Molecules 2005, 10(8), 837-842; doi:10.3390/10080837
Article

Pyrimidine Acyclo-C-Nucleosides by Ring Transformations of 2-Formyl-L-arabinal

1, 1, 2 and 1,*
1 Institut für Chemie der Universität Rostock, D-18051 Rostock, Germany 2 Leibniz-Institut für Organische Katalyse, Buchbinderstr. 5–6, D-18055 Rostock, Germany
* Author to whom correspondence should be addressed.
Received: 29 September 2004 / Revised: 5 April 2005 / Accepted: 5 April 2005 / Published: 31 August 2005
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Abstract

The protected 2-formyl-L-arabinal 2 reacted with thiourea and cyanamide in the presence of sodium hydride to afford via ring transformations the 5-[1R,2S-1,2- bis(benzyloxy)-3-hydroxypropyl]-1,2-dihydropyrimidines 3 and 4, respectively. Similarly, treatment of 2 with 3-amino-2H-1,2,4-triazole yielded 6-[1R,2S-1,2- bis(benzyloxy)-3-hydroxypropyl][1,2,4]-triazolo[1,5-a]pyrimidine (5).
Keywords: Glycals; nucleoside analogues; pyrimidines; fused pyrimidines; push-pull alkenes; ring transformation Glycals; nucleoside analogues; pyrimidines; fused pyrimidines; push-pull alkenes; ring transformation
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Bari, A.; Feist, H.; Michalik, M.; Peseke, K. Pyrimidine Acyclo-C-Nucleosides by Ring Transformations of 2-Formyl-L-arabinal. Molecules 2005, 10, 837-842.

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