volume 364 issue 15 pages 2606-2612

Ring Closure of Nitroalkylmalonates for the Synthesis of Isoxazolines under the Acylation Conditions

Publication typeJournal Article
Publication date2022-07-06
scimago Q1
wos Q1
SJR0.930
CiteScore8.0
Impact factor4.0
ISSN16154150, 16154169
Catalysis
Organic Chemistry
Abstract

Acylation of nitroalkylmalonates was found to yield substituted isoxazoline derivatives. This redox‐neutral transformation has a wide substrate scope and produces target products with yields up to 92%. Various substituents (aryl, alkyl, and ester) at the C3 and C4 positions of the resulting isoxazolines were also tolerated. A quick assembly of the isoxazoline ring starting from nitroalkenes and malonates was successfully developed. Control experiments showed that the intramolecular ring closure is the most likely key mechanistic step. Subsequent transformations into pyrrolidine and furane derivatives demonstrated the synthetic utility of the obtained products.

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Antonova Y. A. et al. Ring Closure of Nitroalkylmalonates for the Synthesis of Isoxazolines under the Acylation Conditions // Advanced Synthesis and Catalysis. 2022. Vol. 364. No. 15. pp. 2606-2612.
GOST all authors (up to 50) Copy
Antonova Y. A., Nelyubina Y. V., Ioffe S. L., Sukhorukov A. Yu., Tabolin A. A. Ring Closure of Nitroalkylmalonates for the Synthesis of Isoxazolines under the Acylation Conditions // Advanced Synthesis and Catalysis. 2022. Vol. 364. No. 15. pp. 2606-2612.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1002/adsc.202200420
UR - https://onlinelibrary.wiley.com/doi/10.1002/adsc.202200420
TI - Ring Closure of Nitroalkylmalonates for the Synthesis of Isoxazolines under the Acylation Conditions
T2 - Advanced Synthesis and Catalysis
AU - Antonova, Yulia A
AU - Nelyubina, Yulia V.
AU - Ioffe, Sema L
AU - Sukhorukov, Alexey Yu
AU - Tabolin, Andrey A
PY - 2022
DA - 2022/07/06
PB - Wiley
SP - 2606-2612
IS - 15
VL - 364
SN - 1615-4150
SN - 1615-4169
ER -
BibTex |
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BibTex (up to 50 authors) Copy
@article{2022_Antonova,
author = {Yulia A Antonova and Yulia V. Nelyubina and Sema L Ioffe and Alexey Yu Sukhorukov and Andrey A Tabolin},
title = {Ring Closure of Nitroalkylmalonates for the Synthesis of Isoxazolines under the Acylation Conditions},
journal = {Advanced Synthesis and Catalysis},
year = {2022},
volume = {364},
publisher = {Wiley},
month = {jul},
url = {https://onlinelibrary.wiley.com/doi/10.1002/adsc.202200420},
number = {15},
pages = {2606--2612},
doi = {10.1002/adsc.202200420}
}
MLA
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MLA Copy
Antonova, Yulia A., et al. “Ring Closure of Nitroalkylmalonates for the Synthesis of Isoxazolines under the Acylation Conditions.” Advanced Synthesis and Catalysis, vol. 364, no. 15, Jul. 2022, pp. 2606-2612. https://onlinelibrary.wiley.com/doi/10.1002/adsc.202200420.