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New Metal‐Free Route towards Imidazole‐Substituted Uridine
Author(s) -
Mattelaer HenriPhilippe,
Van Hool AnneSophie,
de Jong Flip,
Van der Auweraer Mark,
Van Meervelt Luc,
Dehaen Wim,
Herdewijn Piet
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000563
Subject(s) - nucleobase , chemistry , imidazole , moiety , combinatorial chemistry , nucleoside , uracil , aryl , ribose , stereochemistry , organic chemistry , dna , biochemistry , alkyl , enzyme
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.