K. S. Sadovnikov, D. A. Vasilenko, K. N. Sedenkova, V. B. Rybakov, Yu. K. Grishin, V. A. Alferova, T. S. Kuznetsova, E. B. Averina, “Straightforward chemoselective 4-nitration of 5-aminoisoxazoles”, Mendeleev Commun., 2020, Volume 30, Issue 4,Pages <nobr>487

This article is cited in 5 papers

Communications

Straightforward chemoselective 4-nitration of 5-aminoisoxazoles

K. S. Sadovnikov^a, D. A. Vasilenko^a, K. N. Sedenkova^ab, V. B. Rybakov^a, Yu. K. Grishin^a, V. A. Alferova^cd, 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
^c G.F. Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow, Russian Federation
^d National Research University Higher School of Economics (HSE University), Moscow, Russian Federation

Abstract: 5-Aminoisoxazoles bearing 3-positioned electron-withdrawing group react chemoselectively with trifluoroacetyl nitrate (generated from ammonium nitrate and trifluoroacetic anhydride) to give the corresponding 4-nitro derivatives in yields up to 80%. The results were rationalized by computation studies. Several 5-amino-4-nitroisoxazole-3-carboxilic acid derivatives revealed moderate antibacterial activity.

Keywords: isoxazoles, aminoisoxazoles, nitroisoxazoles, nitration, chemoselectivity, trifluoroacetyl nitrate, quantum chemical calculations, antibacterial activity.

Language: English

DOI: 10.1016/j.mencom.2020.07.027

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