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Synthesis 2013; 45(23): 3263-3268
DOI: 10.1055/s-0033-1338539
DOI: 10.1055/s-0033-1338539
paper
Reaction of Cytidine with Cyanopropargylic Alcohols: Synthesis of Functionalized Cytidine Cyclic Ketals
Further Information
Publication History
Received: 21 July 2013
Accepted after revision: 06 September 2013
Publication Date:
23 September 2013 (online)
Abstract
Cytidine reacts with one or two molecules of cyanopropargylic alcohols under mild conditions (K2CO3, DMF, 20–25 °C, 10–48 h) by the hydroxy groups of the ribose moiety to afford representatives of the two novel families of cytidine cyclic ketals. The first ones (53–76% yields) are formed with participation of the two vicinal hydroxyl groups (at 2′,3′-cis-positions) only. The second ones (7–21% yields) represent the adducts of cytidine with two molecules of cyanopropargylic alcohols involving all the three hydroxyl groups.
Key words
cytidine - cyanopropargylic alcohols - nucleophilic addition - cyclization - cyclic ketalsSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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