Synthesis of 2-halo-2Н-azirine-2-carboxylic acid amides and esters by isomerization of 5-(dialkylamino/alkoxy)-substituted isoxazoles, catalyzed by iron(II) sulfate
Publication type: Journal Article
Publication date: 2017-10-01
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
N,N-Dialkylamides and esters of 2-(chloro/bromo/iodo)-2H-azirine-2-carboxylic acids were synthesized by isomerization of 4-halo-5-(dialkylamino/alkoxy)isoxazoles in the presence of catalytic amounts of FeSO4·7H2O. The use of iron(II) sulfate as catalyst, compared to its chloride, provides the advantage of avoiding halide exchange products in isomerization reactions of 4-bromo- and 4-iodoisoxazoles, as well as prevents catalyst deactivation by the 5-amino substituent of isoxazole, compared to rhodium(II) carboxylates.
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Agafonova A. V. et al. Synthesis of 2-halo-2Н-azirine-2-carboxylic acid amides and esters by isomerization of 5-(dialkylamino/alkoxy)-substituted isoxazoles, catalyzed by iron(II) sulfate // Chemistry of Heterocyclic Compounds. 2017. Vol. 53. No. 10. pp. 1068-1071.
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Agafonova A. V., Smetanin I. A., Rostovskii N. V., Khlebnikov A. F., Novikov M. S. Synthesis of 2-halo-2Н-azirine-2-carboxylic acid amides and esters by isomerization of 5-(dialkylamino/alkoxy)-substituted isoxazoles, catalyzed by iron(II) sulfate // Chemistry of Heterocyclic Compounds. 2017. Vol. 53. No. 10. pp. 1068-1071.
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TY - JOUR
DO - 10.1007/s10593-017-2172-z
UR - https://doi.org/10.1007/s10593-017-2172-z
TI - Synthesis of 2-halo-2Н-azirine-2-carboxylic acid amides and esters by isomerization of 5-(dialkylamino/alkoxy)-substituted isoxazoles, catalyzed by iron(II) sulfate
T2 - Chemistry of Heterocyclic Compounds
AU - Agafonova, Anastasiya V
AU - Smetanin, Ilia A
AU - Rostovskii, Nikolai V
AU - Khlebnikov, Alexander F
AU - Novikov, Mikhail S.
PY - 2017
DA - 2017/10/01
PB - Springer Nature
SP - 1068-1071
IS - 10
VL - 53
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2017_Agafonova,
author = {Anastasiya V Agafonova and Ilia A Smetanin and Nikolai V Rostovskii and Alexander F Khlebnikov and Mikhail S. Novikov},
title = {Synthesis of 2-halo-2Н-azirine-2-carboxylic acid amides and esters by isomerization of 5-(dialkylamino/alkoxy)-substituted isoxazoles, catalyzed by iron(II) sulfate},
journal = {Chemistry of Heterocyclic Compounds},
year = {2017},
volume = {53},
publisher = {Springer Nature},
month = {oct},
url = {https://doi.org/10.1007/s10593-017-2172-z},
number = {10},
pages = {1068--1071},
doi = {10.1007/s10593-017-2172-z}
}
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MLA
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Agafonova, Anastasiya V., et al. “Synthesis of 2-halo-2Н-azirine-2-carboxylic acid amides and esters by isomerization of 5-(dialkylamino/alkoxy)-substituted isoxazoles, catalyzed by iron(II) sulfate.” Chemistry of Heterocyclic Compounds, vol. 53, no. 10, Oct. 2017, pp. 1068-1071. https://doi.org/10.1007/s10593-017-2172-z.