Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones
Publication type: Journal Article
Publication date: 2020-07-01
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
1-Acyl-2-azabuta-1,3-dienes underwent rearrangement to 4-pyrrolin-2-ones in the presence of acidic catalysts (silica gel or ZnCl2) and water. The reaction proceeded via the formation of 2,3-dihydroxy-3,4-dihydropyrrole and 2-hydroxy-2Н-pyrrole intermediates, the latter of which was transformed by [1,5]-sigmatropic shift of carbonyl substituent and prototropic isomerization. 4-Chloro-substituted 1-acetyl-2-azabuta-1,3-dienes were stable toward rearrangement, while brominated analogs rearranged into 4-pyrrolin-2-ones, probably as a result of the initial radical hydrodebromination. According to calculations performed at the DFT level, two steps of the reaction were catalyzed by acid: the cyclization of 2-azabutadiene and the sigmatropic shift in the 2-hydroxy-2Н-pyrrole intermediate.
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Rostovskii N. V. et al. Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones // Chemistry of Heterocyclic Compounds. 2020. Vol. 56. No. 7. pp. 881-887.
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Rostovskii N. V., Smetanin I. A., Koronatov A. N., Agafonova A. V., Potapenkov V. V., Khlebnikov A. F., Novikov M. S. Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones // Chemistry of Heterocyclic Compounds. 2020. Vol. 56. No. 7. pp. 881-887.
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TY - JOUR
DO - 10.1007/s10593-020-02745-x
UR - https://doi.org/10.1007/s10593-020-02745-x
TI - Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones
T2 - Chemistry of Heterocyclic Compounds
AU - Rostovskii, Nikolai V
AU - Smetanin, Ilia A
AU - Koronatov, Alexander N
AU - Agafonova, Anastasiya V
AU - Potapenkov, Vasilii V
AU - Khlebnikov, Alexander F
AU - Novikov, Mikhail S.
PY - 2020
DA - 2020/07/01
PB - Springer Nature
SP - 881-887
IS - 7
VL - 56
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2020_Rostovskii,
author = {Nikolai V Rostovskii and Ilia A Smetanin and Alexander N Koronatov and Anastasiya V Agafonova and Vasilii V Potapenkov and Alexander F Khlebnikov and Mikhail S. Novikov},
title = {Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones},
journal = {Chemistry of Heterocyclic Compounds},
year = {2020},
volume = {56},
publisher = {Springer Nature},
month = {jul},
url = {https://doi.org/10.1007/s10593-020-02745-x},
number = {7},
pages = {881--887},
doi = {10.1007/s10593-020-02745-x}
}
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MLA
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Rostovskii, Nikolai V., et al. “Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones.” Chemistry of Heterocyclic Compounds, vol. 56, no. 7, Jul. 2020, pp. 881-887. https://doi.org/10.1007/s10593-020-02745-x.