4-Azidotetrahydroquinazoline derivatives in CuAAC reaction

[Display omitted] 4-Azido-2-methyltetrahydroquinazoline N-oxide cleanly undergoes the copper(i)-catalyzed azide–alkyne cycloaddition (CuAAC) reaction with alkynes to give new conjugates with pyrimidine N-oxide and triazole moieties. Its deoxygenated analogue, 4-azido-2-methyltetrahydroquinazoline, i...

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Bibliographic Details
Published in:Mendeleev communications 2020-11, Vol.30 (6), p.714-716
Main Authors: Nazarova, Anna A., Sedenkova, Kseniya N., Vasilenko, Dmitry A., Grishin, Yuri K., Kuznetsova, Tamara S., Averina, Elena B.
Format: Article
Language:English
Subjects:
azidopyrimidine N-oxides
CuAAC
N-oxides
pyrimidines
quantum chemical calculations
tautomers
triazoles
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Summary:[Display omitted] 4-Azido-2-methyltetrahydroquinazoline N-oxide cleanly undergoes the copper(i)-catalyzed azide–alkyne cycloaddition (CuAAC) reaction with alkynes to give new conjugates with pyrimidine N-oxide and triazole moieties. Its deoxygenated analogue, 4-azido-2-methyltetrahydroquinazoline, is inert in CuACC process due to the shift of imidoyl azide–tetrazole equilibrium towards the tetrazole tautomer.
ISSN:0959-9436
DOI:10.1016/j.mencom.2020.11.008