Fe(II)-Catalyzed Isomerization of 5-Chloroisoxazoles to 2 H -Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole-Nitrogen Heterocycle Dyads
Publication type: Journal Article
Publication date: 2018-02-15
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
29444569
Organic Chemistry
Abstract
2-(1 H-Pyrazol-1-ylcarbonyl)-2 H-azirines were synthesized by in situ trapping of 2 H-azirine-2-carbonyl chlorides, generated by Fe(II)-catalyzed isomerization of 5-chloroisoxazoles, with pyrazoles. According to DFT calculations, the selectivity of nucleophilic substitution at the carbonyl group of 2 H-azirine-2-carbonyl chloride by a pyrazole nucleophile, which is a mixture of two tautomers, is controlled by thermodynamic factors. 2-(1 H-Pyrazol-1-ylcarbonyl)-2 H-azirines are excellent precursors for the preparation of two other pyrazole-nitrogen heterocycle dyads: 5-(1 H-pyrazol-1-yl)oxazoles by photolysis and 1-(1 H-pyrrol-2-ylcarbonyl)-1 H-pyrazoles by a Ni(II)-catalyzed reaction with 1,3-dicarbonyl compounds. 5-(1 H-Pyrazol-1-yl)oxazoles show strong emission in acetonitrile at 360-410 nm with high quantum yields.
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Total citations:
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Citations from 2024:
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GOST
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Mikhailov K. et al. Fe(II)-Catalyzed Isomerization of 5-Chloroisoxazoles to 2 H -Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole-Nitrogen Heterocycle Dyads // Journal of Organic Chemistry. 2018. Vol. 83. No. 6. pp. 3177-3187.
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Mikhailov K., Galenko E. E., Galenko A. V., Novikov M. S., Ivanov A. Yu., Starova G. L., Starova G. L., Khlebnikov A. F. Fe(II)-Catalyzed Isomerization of 5-Chloroisoxazoles to 2 H -Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole-Nitrogen Heterocycle Dyads // Journal of Organic Chemistry. 2018. Vol. 83. No. 6. pp. 3177-3187.
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TY - JOUR
DO - 10.1021/acs.joc.8b00069
UR - https://pubs.acs.org/doi/10.1021/acs.joc.8b00069
TI - Fe(II)-Catalyzed Isomerization of 5-Chloroisoxazoles to 2 H -Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole-Nitrogen Heterocycle Dyads
T2 - Journal of Organic Chemistry
AU - Mikhailov, Kirill
AU - Galenko, Ekaterina E
AU - Galenko, Alexey V
AU - Novikov, Mikhail S.
AU - Ivanov, Alexander Yu
AU - Starova, G. L.
AU - Starova, Galina L
AU - Khlebnikov, Alexander F
PY - 2018
DA - 2018/02/15
PB - American Chemical Society (ACS)
SP - 3177-3187
IS - 6
VL - 83
PMID - 29444569
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2018_Mikhailov,
author = {Kirill Mikhailov and Ekaterina E Galenko and Alexey V Galenko and Mikhail S. Novikov and Alexander Yu Ivanov and G. L. Starova and Galina L Starova and Alexander F Khlebnikov},
title = {Fe(II)-Catalyzed Isomerization of 5-Chloroisoxazoles to 2 H -Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole-Nitrogen Heterocycle Dyads},
journal = {Journal of Organic Chemistry},
year = {2018},
volume = {83},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.8b00069},
number = {6},
pages = {3177--3187},
doi = {10.1021/acs.joc.8b00069}
}
Cite this
MLA
Copy
Mikhailov, Kirill, et al. “Fe(II)-Catalyzed Isomerization of 5-Chloroisoxazoles to 2 H -Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole-Nitrogen Heterocycle Dyads.” Journal of Organic Chemistry, vol. 83, no. 6, Feb. 2018, pp. 3177-3187. https://pubs.acs.org/doi/10.1021/acs.joc.8b00069.