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Molecules 2005, 10(8), 837-842; https://doi.org/10.3390/10080837

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

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). View Full-Text
Keywords: Glycals; nucleoside analogues; pyrimidines; fused pyrimidines; push-pull alkenes; ring transformation Glycals; nucleoside analogues; pyrimidines; fused pyrimidines; push-pull alkenes; ring transformation
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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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