Fe(II)-Catalyzed Isomerization of 4-Vinylisoxazoles into Pyrroles
Publication type: Journal Article
Publication date: 2017-08-02
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
28726412
Organic Chemistry
Abstract
The first synthesis of pyrroles by Fe(II)-catalyzed isomerization of 4-vinylisoxazoles is reported. 5-Alkoxy, amino, and N,N-dialkylamino-3-aryl/alkyl-4-(2-R-vinyl)isoxazoles afford 2-aryl/alkyl-5-aryl/alkyl/methoxycarbonyl-1H-pyrrol-3-carboxylic acid derivatives typically under mild conditions with cheap and available FeCl2·4H2O as a catalyst. The isomerization of 5-alkoxy/amino-3-arylisoxazoles, bearing unsaturated carbo and heterocyclic substituents at the position 4, gives the corresponding fused pyrrolecarboxylic acid derivatives in high yields. DFT calculations were used to elucidate a probable mechanism of the isomerization and explain the influence of steric congestion of the vinyl moiety on the isomerization pathway.
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Citations from 2024:
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GOST
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Galenko E. E. et al. Fe(II)-Catalyzed Isomerization of 4-Vinylisoxazoles into Pyrroles // Journal of Organic Chemistry. 2017. Vol. 82. No. 16. pp. 8568-8579.
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Galenko E. E., Bodunov V. A., Galenko A. V., Novikov M. S., Khlebnikov A. F. Fe(II)-Catalyzed Isomerization of 4-Vinylisoxazoles into Pyrroles // Journal of Organic Chemistry. 2017. Vol. 82. No. 16. pp. 8568-8579.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.joc.7b01351
UR - https://pubs.acs.org/doi/10.1021/acs.joc.7b01351
TI - Fe(II)-Catalyzed Isomerization of 4-Vinylisoxazoles into Pyrroles
T2 - Journal of Organic Chemistry
AU - Galenko, Ekaterina E
AU - Bodunov, Vladimir A
AU - Galenko, Alexey V
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F
PY - 2017
DA - 2017/08/02
PB - American Chemical Society (ACS)
SP - 8568-8579
IS - 16
VL - 82
PMID - 28726412
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2017_Galenko,
author = {Ekaterina E Galenko and Vladimir A Bodunov and Alexey V Galenko and Mikhail S. Novikov and Alexander F Khlebnikov},
title = {Fe(II)-Catalyzed Isomerization of 4-Vinylisoxazoles into Pyrroles},
journal = {Journal of Organic Chemistry},
year = {2017},
volume = {82},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.7b01351},
number = {16},
pages = {8568--8579},
doi = {10.1021/acs.joc.7b01351}
}
Cite this
MLA
Copy
Galenko, Ekaterina E., et al. “Fe(II)-Catalyzed Isomerization of 4-Vinylisoxazoles into Pyrroles.” Journal of Organic Chemistry, vol. 82, no. 16, Aug. 2017, pp. 8568-8579. https://pubs.acs.org/doi/10.1021/acs.joc.7b01351.