A. A. Nazarova, K. N. Sedenkova, D. A. Vasilenko, Yu. K. Grishin, T. S. Kuznetsova, E. B. Averina, “4-Azidotetrahydroquinazoline derivatives in CuAAC reaction”, Mendeleev Commun., 2020, Volume 30, Issue 6,Pages <nobr>714

This article is cited in 7 papers

Communications

4-Azidotetrahydroquinazoline derivatives in CuAAC reaction

A. A. Nazarova^a, K. N. Sedenkova^ab, D. A. Vasilenko^a, Yu. K. Grishin^a, T. S. Kuznetsova^a, E. B. Averina^ab

^a Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
^b Institute of Physiologically Active Compounds, Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, Chernogolovka, Moscow Region, Russian Federation

Abstract: 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.

Keywords: pyrimidines, triazoles, CuAAC, N-oxides, tautomers, azidopyrimidine N-oxides, quantum chemical calculations.

Language: English

DOI: 10.1016/j.mencom.2020.11.008

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