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Convenient preparation of arylnitromethanes by oxidation of benzaldoximes with urea hydrogen peroxide

Anna Sergeevna Maksimenko 1
Anna Sergeevna Maksimenko
, 
Ivan Aleksandrovich Koblov 1
Ivan Aleksandrovich Koblov
, 
Natalya B Chernysheva 1
Natalya B Chernysheva
, 
Victor Petrovich Kislyi 1
Victor Petrovich Kislyi
, 
Victor Vladimirovich Semenov 1
Victor Vladimirovich Semenov
10.1016/j.mencom.2021.11.016
Published 2021-11-08
Communication , Volume 31, Issue 6, 818-820
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Maksimenko A. S. et al. Convenient preparation of arylnitromethanes by oxidation of benzaldoximes with urea hydrogen peroxide // Mendeleev Communications. 2021. Vol. 31. No. 6. pp. 818-820.
GOST all authors (up to 50) Copy
Maksimenko A. S., Koblov I. A., Chernysheva N. B., Kislyi V. P., Semenov V. V. Convenient preparation of arylnitromethanes by oxidation of benzaldoximes with urea hydrogen peroxide // Mendeleev Communications. 2021. Vol. 31. No. 6. pp. 818-820.
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TY - JOUR
DO - 10.1016/j.mencom.2021.11.016
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.11.016
TI - Convenient preparation of arylnitromethanes by oxidation of benzaldoximes with urea hydrogen peroxide
T2 - Mendeleev Communications
AU - Maksimenko, Anna Sergeevna
AU - Koblov, Ivan Aleksandrovich
AU - Chernysheva, Natalya B
AU - Kislyi, Victor Petrovich
AU - Semenov, Victor Vladimirovich
PY - 2021
DA - 2021/11/08
PB - Mendeleev Communications
SP - 818-820
IS - 6
VL - 31
ER -
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@article{2021_Maksimenko,
author = {Anna Sergeevna Maksimenko and Ivan Aleksandrovich Koblov and Natalya B Chernysheva and Victor Petrovich Kislyi and Victor Vladimirovich Semenov},
title = {Convenient preparation of arylnitromethanes by oxidation of benzaldoximes with urea hydrogen peroxide},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.11.016},
number = {6},
pages = {818--820},
doi = {10.1016/j.mencom.2021.11.016}
}
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Maksimenko, Anna Sergeevna, et al. “Convenient preparation of arylnitromethanes by oxidation of benzaldoximes with urea hydrogen peroxide.” Mendeleev Communications, vol. 31, no. 6, Nov. 2021, pp. 818-820. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.11.016.

Keywords

aldoximes
arylnitromethanes
hydrogen peroxide
oxidation
perborate
urea

Abstract

Arylnitromethanes were prepared by oxidation of aldoximes with sodium perborate or with urea hydrogen peroxide in the presence of boric acid. The use of urea hydrogen peroxide complex provides better and more stable yields of nitro compound and allows one to halve an acetic acid consumption. Only E-aldoximes are oxidized to arylnitromethanes while Z-isomers are transformed into complex mixtures not containing arylnitromethanes.

References

2.
Selective and Potent Morpholinone Inhibitors of the MDM2–p53 Protein–Protein Interaction
Gonzalez A.Z., Eksterowicz J., Bartberger M.D., Beck H.P., Canon J., Chen A., Chow D., Duquette J., Fox B.M., Fu J., Huang X., Houze J.B., Jin L., Li Y., Li Z., et. al.
Journal of Medicinal Chemistry, 2014
3.
(a) F. Nietzold, S. Rubner and T. Berg, Chem. Commun., 2019, 55, Asian J., 2015, 10, 334.
4.
Formation of 3,4-Diarylpyrrole- and Pyrrolocoumarin Core of Natural Marine Products via Barton-Zard Reaction and Selective O-Demethylation
Silyanova E.A., Samet A.V., Salamandra L.K., Khrustalev V.N., Semenov V.V.
European Journal of Organic Chemistry, 2020
5.
Sea Urchin Embryo Model As a Reliable in Vivo Phenotypic Screen to Characterize Selective Antimitotic Molecules. Comparative evaluation of Combretapyrazoles, -isoxazoles, -1,2,3-triazoles, and -pyrroles as Tubulin-Binding Agents.
Semenova M.N., Demchuk D.V., Tsyganov D.V., Chernysheva N.B., Samet A.V., Silyanova E.A., Kislyi V.P., Maksimenko A.S., Varakutin A.E., Konyushkin L.D., Raihstat M.M., Kiselyov A.S., Semenov V.V.
ACS Combinatorial Science, 2018
6.
Regioselective synthesis of 3,4-diaryl-5-unsubstituted isoxazoles, analogues of natural cytostatic combretastatin A4.
Chernysheva N.B., Maksimenko A.S., Andreyanov F.A., Kislyi V.P., Strelenko Y.A., Khrustalev V.N., Semenova M.N., Semenov V.V.
European Journal of Medicinal Chemistry, 2018
7.
10.1016/j.mencom.2021.11.016_b0025
Ono
The Nitro Group in Organic Synthesis, ed, 2001
8.
(a) G. Occhipinti, L. Liguori, A. Tsoukala and H. R. Bjorsvik, Org.
9.
A Switchable Oxidation Process Leading to Two Various Versatile Pharmaceutical Intermediates
Occhipinti G., Liguori L., Tsoukala A., Bjørsvik H.
Organic Process Research and Development, 2010
11.
Ozone-mediated nitration of alkylbenzenes and related compounds with nitrogen dioxide
Suzuki H., Murashima T., Kozai I., Mori T.
Journal of the Chemical Society Perkin Transactions 1, 1993
13.
Convenient preparation of ring-methoxylated phenylnitromethanes
Hauser F.M., Baghdanov V.M.
Journal of Organic Chemistry, 1988
14.
KMnO4-Mediated Oxidation as a Continuous Flow Process
Sedelmeier J., Ley S.V., Baxendale I.R., Baumann M.
Organic Letters, 2010
18.
Unanticipated Silyl Transfer in Enantioselective α,β-Unsaturated Acyl Ammonium Catalysis Using Silyl Nitronates
Matviitsuk A., Greenhalgh M.D., Taylor J.E., Nguyen X.B., Cordes D.B., Slawin A.M., Lupton D.W., Smith A.D.
Organic Letters, 2019
19.
C(sp2) – H functionalization of aldimines and related compounds: advances and prospects
Akulov A.A., Varaksin M.V., Charushin V.N., Chupakhin O.N.
Russian Chemical Reviews, 2021
22.
Development of an Intermittent-Flow Enantioselective Aza-Henry Reaction Using an Arylnitromethane and Homogeneous Brønsted Acid–Base Catalyst with Recycle
Tsukanov S.V., Johnson M.D., May S.A., Rosemeyer M., Watkins M.A., Kolis S.P., Yates M.H., Johnston J.N.
Organic Process Research and Development, 2016
23.
Organocatalytic, Diastereo- and Enantioselective Synthesis of Nonsymmetric cis-Stilbene Diamines: A Platform for the Preparation of Single-Enantiomer cis-Imidazolines for Protein–Protein Inhibition
Vara B.A., Mayasundari A., Tellis J.C., Danneman M.W., Arredondo V., Davis T.A., Min J., Finch K., Guy R.K., Johnston J.N.
Journal of Organic Chemistry, 2014
24.
A Versatile Method for the Conversion of Oximes to Nitroalkanes
Base D.S., Vanajatha G.
Synthetic Communications, 1998
26.
Continuous Platform To Generate Nitroalkanes On-Demand (in Situ) Using Peracetic Acid-Mediated Oxidation in a PFA Pipes-in-Series Reactor
Tsukanov S.V., Johnson M.D., May S.A., Kolis S.P., Yates M.H., Johnston J.N.
Organic Process Research and Development, 2018
28.
Peroxytrifluoroacetic Acid. VI. The Oxidation of Oximes to Nitroparaffins1,2
Emmons W.D., Pagano A.S.
Journal of the American Chemical Society, 1955
29.
Sodium perborate and sodium percarbonate: further applications in organic synthesis
McKillop A., Sanderson W.R.
Journal of the Chemical Society Perkin Transactions 1, 2000
30.
(a) M. A. A. F. de C. T. Carrondo and A. C. Skapski, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem., 1978, 34, 3551
31.
The B11 Nuclear Magnetic Resonance Chemical Shifts and Spin Coupling Values for Various Compounds
Onak T., Landesman H., Williams R., Shapiro I.
The Journal of Physical Chemistry, 1959
32.
Nature of peroxoborate species in aqueous solution: a study by boron-11 nuclear magnetic resonance and Raman spectroscopy
Flanagan J., Griffith W.P., Powell R.D., West A.P.
Journal of the Chemical Society Dalton Transactions, 1989
33.
(d) B. N. Chernyshov, O. V. Brovkina, B. Ya. Kavun and E. B. Pashnina, Russ. J. Inorg. Chem., 1996, 41, 1705 (Zh. Neorg. Khim., 1996, 41, 1798). 13 M. S. Manna and S. Mukherjee, J. Am. Chem. Soc., 2015, 137, 130.
34.
Kinetics and mechanism of diethyl sulfide oxidation by sodium peroxoborate in aqueous solutions
Lobachev V.L., Dyatlenko L.M., Zubritskii M.Y.
Kinetics and Catalysis, 2016
35.
Spectroscopic investigation into the nature of the active sites for epoxidation reactions using vanadium-based aluminophosphate catalysts
Vishnuvarthan M., James Paterson A., Raja R., Piovano A., Bonino F., Gianotti E., Berlier G.
Microporous and Mesoporous Materials, 2011
36.
A high-performance selective oxidation system for the facile production of fine chemicals
Raja R., Thomas J.M., Greenhill-Hooper M., Doukova V.
Chemical Communications, 2007
37.
10.1016/j.mencom.2021.11.016_b0075
Pinnick
Org. React., 1990
38.
10.1016/j.mencom.2021.11.016_b0080
Gawley
Org. React., 1988