Home / Publications / Straightforward chemoselective 4-nitration of 5-aminoisoxazoles

Straightforward chemoselective 4-nitration of 5-aminoisoxazoles

Kirill Sergeyevich Sadovnikov 1
Kirill Sergeyevich Sadovnikov
, 
Dmitry Alekseevich Vasilenko 1
Dmitry Alekseevich Vasilenko
,  , 
Viktor Borisovich Rybakov 1
Viktor Borisovich Rybakov
,  , 
Vera Aleksandrovna Alferova 3, 4
Vera Aleksandrovna Alferova
, 
Tamara Stepanovna Kuznetsova 1
Tamara Stepanovna Kuznetsova
, 
Elena Borisovna Averina 1, 2
Elena Borisovna Averina
10.1016/j.mencom.2020.07.027
Published 2020-06-26
Communication , Volume 30, Issue 4, 487-489
5
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Sadovnikov K. S. et al. Straightforward chemoselective 4-nitration of 5-aminoisoxazoles // Mendeleev Communications. 2020. Vol. 30. No. 4. pp. 487-489.
GOST all authors (up to 50) Copy
Sadovnikov K. S., Vasilenko D. A., Sedenkova K. N., Rybakov V. B., Grishin Y. K., Alferova V. A., Kuznetsova T. S., Averina E. B. Straightforward chemoselective 4-nitration of 5-aminoisoxazoles // Mendeleev Communications. 2020. Vol. 30. No. 4. pp. 487-489.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2020.07.027
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.027
TI - Straightforward chemoselective 4-nitration of 5-aminoisoxazoles
T2 - Mendeleev Communications
AU - Sadovnikov, Kirill Sergeyevich
AU - Vasilenko, Dmitry Alekseevich
AU - Sedenkova, Kseniya N
AU - Rybakov, Viktor Borisovich
AU - Grishin, Yuri Konstantinovich
AU - Alferova, Vera Aleksandrovna
AU - Kuznetsova, Tamara Stepanovna
AU - Averina, Elena Borisovna
PY - 2020
DA - 2020/06/26
PB - Mendeleev Communications
SP - 487-489
IS - 4
VL - 30
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2020_Sadovnikov,
author = {Kirill Sergeyevich Sadovnikov and Dmitry Alekseevich Vasilenko and Kseniya N Sedenkova and Viktor Borisovich Rybakov and Yuri Konstantinovich Grishin and Vera Aleksandrovna Alferova and Tamara Stepanovna Kuznetsova and Elena Borisovna Averina},
title = {Straightforward chemoselective 4-nitration of 5-aminoisoxazoles},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.027},
number = {4},
pages = {487--489},
doi = {10.1016/j.mencom.2020.07.027}
}
MLA
Cite this
MLA Copy
Sadovnikov, Kirill Sergeyevich, et al. “Straightforward chemoselective 4-nitration of 5-aminoisoxazoles.” Mendeleev Communications, vol. 30, no. 4, Jun. 2020, pp. 487-489. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.027.

Keywords

aminoisoxazoles
Antibacterial activity
chemoselectivity
isoxazoles
nitration
nitroisoxazoles
quantum chemical calculations
trifluoroacetyl nitrate

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.

References

1.
Medicinal Chemistry Perspective of Fused Isoxazole Derivatives.
A. Barmade M., R. Murumkar P., Kumar Sharma M., Ram Yadav M.
Current Topics in Medicinal Chemistry, 2016
3.
Isoxazole ring as a useful scaffold in a search for new therapeutic agents
Sysak A., Obmińska-Mrukowicz B.
European Journal of Medicinal Chemistry, 2017
4.
The recent progress of isoxazole in medicinal chemistry
Zhu J., Mo J., Lin H., Chen Y., Sun H.
Bioorganic and Medicinal Chemistry, 2018
5.
Tsyganov D.V., Semenova M.N., Konyushkin L.D., Ushkarov V.I., Raihstat M.M., Semenov V.V.
Mendeleev Communications, 2019
6.
10.1016/j.mencom.2020.07.027_sbref0010a
Doi
2015
7.
10.1016/j.mencom.2020.07.027_sbref0010b
Farrington
Clinical Pharmacology, 2012
8.
Zonisamide: chemistry, mechanism of action, and pharmacokinetics
Leppik I.E.
Seizure : the journal of the British Epilepsy Association, 2004
9.
Comparative efficacy and tolerability of 15 antipsychotic drugs in schizophrenia: a multiple-treatments meta-analysis
Leucht S., Cipriani A., Spineli L., Mavridis D., Örey D., Richter F., Samara M., Barbui C., Engel R.R., Geddes J.R., Kissling W., Stapf M.P., Lässig B., Salanti G., Davis J.M., et. al.
The Lancet, 2013
10.
Long‐term treatment of depression with isocarboxazide
Larsen J.K., Rafaelsen O.J.
Acta Psychiatrica Scandinavica, 1980
12.
Leflunomide for the Treatment of Rheumatoid Arthritis and Autoimmunity
Sanders S., Harisdangkul V.
American Journal of the Medical Sciences, 2002
14.
Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5-Nitroisoxazoles
Volkova Y.A., Averina E.B., Vasilenko D.A., Sedenkova K.N., Grishin Y.K., Bruheim P., Kuznetsova T.S., Zefirov N.S.
Journal of Organic Chemistry, 2019
15.
Heterocyclization of electrophilic alkenes with tetranitromethane revisited: regiochemistry and the mechanism of nitroisoxazole formation
Averina E.B., Samoilichenko Y.V., Volkova Y.A., Grishin Y.K., Rybakov V.B., Kutateladze A.G., Elyashberg M.E., Kuznetsova T.S., Zefirov N.S.
Tetrahedron Letters, 2012
16.
Chemoselective Reduction of Functionalized 5-Nitroisoxazoles: Synthesis of 5-Amino- and 5-[Hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles
Averina E., Vasilenko D., Samoilichenko Y., Grishin Y., Rybakov V., Kuznetsova T., Zefirov N.
Synthesis, 2014
17.
Synthetic Approaches to Nitro-Substituted Isoxazoles
Averina E., Vasilenko D., Sedenkova K., Kuznetsova T.
Synthesis, 2019
18.
Synthesis of 4-Nitroisoxazoles via NO/NO2-Mediated Heterocyclization of Aryl-Substituted α,β-Unsaturated Ketones
Averina E.B., Vasilenko D.A., Sadovnikov K.S., Sedenkova K.N., Kurova A.V., Grishin Y.K., Kuznetsova T.S., Rybakov V.B., Volkova Y.A.
Synthesis, 2020
19.
Trifluoroacetyl as an Orthogonal Protecting Group for Guanidines
Bartoli S., Jensen K.B., Kilburn J.D.
Journal of Organic Chemistry, 2003