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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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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