Electroreductive Intermolecular
Coupling of Uracils
with Aromatic Ketones: Synthesis of 6‑Substituted and <i>cis</i>-5,6-Disubstituted 5,6-Dihydro-1,3-dimethyluracils and
Their Transformation to 6‑Substituted 1,3-Dimethyluracils, <i>trans</i>-5,6-Disubstituted 5,6-Dihydro-1,3-dimethyluracils,
and 4,5,5-Trisubstituted 3‑Methyloxazolizin-2-ones
Naoki Kise
Yusuke Hamada
Toshihiko Sakurai
10.1021/acs.joc.6b00670.s004
https://acs.figshare.com/articles/dataset/Electroreductive_Intermolecular_Coupling_of_Uracils_with_Aromatic_Ketones_Synthesis_of_6_Substituted_and_i_cis_i_-5_6-Disubstituted_5_6-Dihydro-1_3-dimethyluracils_and_Their_Transformation_to_6_Substituted_1_3-Dimethyluracils_i_trans_i_-5_6-Disubstituted_/3405307
The electroreductive
coupling of 1,3-dimethyluracil, thymine, and
5-fluorouracil with aromatic ketones in the presence of TMSCl gave
6-substituted and <i>cis</i>-5,6-disubstituted 5,6-dihydro-1,3-dimethyluracils.
The dehydrotrimethylsiloxylation of the adducts afforded
6-substituted and 5,6-fused 1,3-dimethyluracils. The detrimethylsilylation
of the adducts with TBAF or 1 M HCl–MeOH gave 4,5,5-trisubstituted
3-methyloxazolizin-2-ones or 3-methyloxazolizin-2-imines
in addition to simply desilylated alcohols. The <i>cis</i>-5,6-disubstituted 5,6-dihydro-1,3-dimethyluracils were isomerized
to the corresponding <i>trans</i>-isomers by heating in
the presence of cat. DMAP. The <i>cis</i>- and <i>trans</i>-5,6-disubstituted 5,6-dihydro-1,3-dimethyluracils were assigned
by the coupling constants <i>J</i><sub>5,6</sub> of their <sup>1</sup>H NMR spectra.
2016-05-12 00:00:00
adduct
ci
presence
dimethyluracil
Aromatic Ketones
Electroreductive Intermolecular
methyl
1 H NMR spectra
Substituted
DMAP
Disubstituted
Dihydro
desilylated alcohols
tran
disubstituted
TBAF
dihydro