1. New Metal-Free Route towards Imidazole-Substituted Uridine
- Author
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Mattelaer, Henri-Philipppe, Van Hool, Anne-Sophie, de Jong, Flip, Van der Auweraer, Mark, Van Meervelt, Luc, Dehaen, Wim, and Herdewijn, Piet
- Subjects
Chemistry ,Science & Technology ,Nucleobases ,Green chemistry ,Physical Sciences ,NUCLEOSIDE ANALOGS ,Chemistry, Organic ,Fluorescent probes ,Nucleosides ,EXPEDIENT ,Fleximers - Abstract
Nucleosides with a bi(hetero)aryl nucleobase have unique potential applications as antiviral drugs and molecular probes. The need for transition metal catalysis to synthesize these nucleosides from pre-functionalized building blocks and the use of nucleobase protection groups results in expensive and tedious syntheses. Herein we report that 5-imidazolyl-uracil can be obtained by scalable Van Leusen imidazole synthesis and regioselectively introduced on ribose to obtain the desired nucleoside in a 5 step synthesis (total yield 55 %). The 5-imidazolyl moiety leads to improved fluorescence properties. The only side-product formed was characterized by 2D-NMR and X-ray crystallography and could be suppressed during synthesis in favor of the desired product. ispartof: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY vol:2020 issue:26 pages:4022-4025 ispartof: location:Germany status: published
- Published
- 2020