In:
European Journal of Organic Chemistry, Wiley, Vol. 2020, No. 26 ( 2020-07-15), p. 4022-4025
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.
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2020.26
DOI:
10.1002/ejoc.202000563
Language:
English
Publisher:
Wiley
Publication Date:
2020
detail.hit.zdb_id:
1475010-7