Home / Publications / Synthesis of 3,4-diarylisoxazoline N-oxides from nitrostilbenes and nitroacetates

Synthesis of 3,4-diarylisoxazoline N-oxides from nitrostilbenes and nitroacetates

Nikita A. Kuznetsov 1, 2
Nikita A. Kuznetsov
, 
Olga A. Bogomolova 2
Olga A. Bogomolova
, 
Ivan A. Koblov 1
Ivan A. Koblov
, 
Alexander V. Samet 1
Alexander V. Samet
, 
Victor Vladimirovich Semenov 1
Victor Vladimirovich Semenov
10.71267/mencom.7584
Published 2025-01-24
Communication , Volume 35, Issue 1, 22-23
1
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Kuznetsov N. A. et al. Synthesis of 3,4-diarylisoxazoline N-oxides from nitrostilbenes and nitroacetates // Mendeleev Communications. 2025. Vol. 35. No. 1. pp. 22-23.
GOST all authors (up to 50) Copy
Kuznetsov N. A., Bogomolova O. A., Koblov I. A., Samet A. V., Semenov V. V. Synthesis of 3,4-diarylisoxazoline N-oxides from nitrostilbenes and nitroacetates // Mendeleev Communications. 2025. Vol. 35. No. 1. pp. 22-23.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.71267/mencom.7584
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7584
TI - Synthesis of 3,4-diarylisoxazoline N-oxides from nitrostilbenes and nitroacetates
T2 - Mendeleev Communications
AU - Kuznetsov, Nikita A.
AU - Bogomolova, Olga A.
AU - Koblov, Ivan A.
AU - Samet, Alexander V.
AU - Semenov, Victor Vladimirovich
PY - 2025
DA - 2025/01/24
PB - Mendeleev Communications
SP - 22-23
IS - 1
VL - 35
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2025_Kuznetsov,
author = {Nikita A. Kuznetsov and Olga A. Bogomolova and Ivan A. Koblov and Alexander V. Samet and Victor Vladimirovich Semenov},
title = {Synthesis of 3,4-diarylisoxazoline N-oxides from nitrostilbenes and nitroacetates},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {Jan},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7584},
number = {1},
pages = {22--23},
doi = {10.71267/mencom.7584}
}
MLA
Cite this
MLA Copy
Kuznetsov, Nikita A., et al. “Synthesis of 3,4-diarylisoxazoline N-oxides from nitrostilbenes and nitroacetates.” Mendeleev Communications, vol. 35, no. 1, Jan. 2025, pp. 22-23. https://mendcomm.colab.ws/publications/10.71267/mencom.7584.

Keywords

3
4
4-diarylisoxazoline N-oxides
5-diarylisoxazoline N-oxides
alkyl nitroacetates
nitrostilbenes
pyridinium ylides.

Abstract

A base-catalyzed reaction of nitrostilbenes with alkyl nitroacetates proceeds regioselectively to afford 3,4-diarylisoxazoline N-oxides as sole or major products. In some cases small amounts of 4,5-diarylisoxazoline N-oxides were formed as side products.

Funders

Russian Science Foundation
24-23-00109

References

.
Silyanova E.A., Ushkarov V.I., Samet A.V., Maksimenko A.S., Koblov I.A., Kislyi V.P., Semenova M.N., Semenov V.V.
Mendeleev Communications, 2022
.
Recent Advances in the Synthesis and Chemistry of Nitronates
Tabolin A., Sukhorukov A., Ioffe S., Dilman A.
Synthesis, 2017
.
Effective Synthesis of 3,4-Diaryl-isoxazole-5-carboxamides and their Antiproliferative Properties
Maksimenko A.S., Kislyi V.P., Chernysheva N.B., Strelenko Y.A., Zubavichus Y.V., Khrustalev V.N., Semenova M.N., Semenov V.V.
European Journal of Organic Chemistry, 2019
.
Ylide formal [4 + 1] annulation.
Zhu C., Ding Y., Ye L.
Organic and Biomolecular Chemistry, 2015
.
Ethyl α‐Nitrocinnamates in the Synthesis of Highly Functionalized Isoxazoles
Chen K., Chen Y., Chuang C.
European Journal of Organic Chemistry, 2010
.
A New Synthesis of α-Amino Acid Derivatives Employing Methyl Nitroacetate as a Versatile Glycine Template
Fornicola R.S., Oblinger E., Montgomery J.
Journal of Organic Chemistry, 1998
.
Synthesis of ?-functional nitro compounds by the nitration of activated carbonyl compounds in a two-phase system
Kislyi V.P., Laikhter A.L., Ugrak B.I., Semenov V.V.
Russian Chemical Bulletin, 1994
.
Toward “E‐ring‐free” lamellarin analogues: synthesis and preliminary biological evaluation
Rusanov D.A., Alfadul S.M., Portnyagina E.Y., Silyanova E.A., Kuznetsov N.A., Podpovetny K.E., Samet A.V., Semenov V.V., Babak M.
ChemBioChem, 2023