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

doi:10.3390/10080837

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

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

Ahmed Bari¹, Holger Feist¹, Manfred Michalik² and Klaus Peseke^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; in revised form: 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

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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.

AMA Style

Bari A, Feist H, Michalik M, Peseke K. Pyrimidine Acyclo-C-Nucleosides by Ring Transformations of 2-Formyl-L-arabinal. Molecules. 2005; 10(8):837-842.

Chicago/Turabian Style

Bari, Ahmed; Feist, Holger; Michalik, Manfred; Peseke, Klaus. 2005. "Pyrimidine Acyclo-C-Nucleosides by Ring Transformations of 2-Formyl-L-arabinal." Molecules 10, no. 8: 837-842.

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