One-pot synthesis of 3-(pyridin-2-yl)-2,3-dihydroazetes via Rh(II)-catalyzed reaction of diazoesters with trimethylsilyl-protected 2-(pyridin-2-yl)-2H-azirines
Publication type: Journal Article
Publication date: 2019-12-27
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
A one-pot method for the synthesis of 3-(pyridin-2-yl)-2,3-dihydroazetes was developed on the basis of Rh2(esp)2-catalyzed reaction of diazoesters with 3-aryl-2-(pyridin-2-yl)-2H-azirines. To prevent deactivation of the catalyst with the pyridine-containing azirine reactant, the trimethylsilyl protection of pyridine nitrogen was used. The insertion and removal of the protecting group were carried out as a onepot synthesis. Reactions involving ethyl 2-diazo-3,3,3-trifluoropropanoate proceed stereoselectively with the formation of only the (2RS,3SR)-isomer of the dihydroazete, which is due to the thermodynamic control of the process.
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Citations from 2024:
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Koronatov A. N. et al. One-pot synthesis of 3-(pyridin-2-yl)-2,3-dihydroazetes via Rh(II)-catalyzed reaction of diazoesters with trimethylsilyl-protected 2-(pyridin-2-yl)-2H-azirines // Chemistry of Heterocyclic Compounds. 2019. Vol. 55. No. 12. pp. 1185-1189.
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Koronatov A. N., Rostovskii N. V., Khlebnikov A. F., Novikov M. S. One-pot synthesis of 3-(pyridin-2-yl)-2,3-dihydroazetes via Rh(II)-catalyzed reaction of diazoesters with trimethylsilyl-protected 2-(pyridin-2-yl)-2H-azirines // Chemistry of Heterocyclic Compounds. 2019. Vol. 55. No. 12. pp. 1185-1189.
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TY - JOUR
DO - 10.1007/s10593-019-02599-y
UR - https://doi.org/10.1007/s10593-019-02599-y
TI - One-pot synthesis of 3-(pyridin-2-yl)-2,3-dihydroazetes via Rh(II)-catalyzed reaction of diazoesters with trimethylsilyl-protected 2-(pyridin-2-yl)-2H-azirines
T2 - Chemistry of Heterocyclic Compounds
AU - Koronatov, Alexander N
AU - Rostovskii, Nikolai V
AU - Khlebnikov, Alexander F
AU - Novikov, Mikhail S.
PY - 2019
DA - 2019/12/27
PB - Springer Nature
SP - 1185-1189
IS - 12
VL - 55
SN - 0009-3122
SN - 1573-8353
ER -
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BibTex (up to 50 authors)
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@article{2019_Koronatov,
author = {Alexander N Koronatov and Nikolai V Rostovskii and Alexander F Khlebnikov and Mikhail S. Novikov},
title = {One-pot synthesis of 3-(pyridin-2-yl)-2,3-dihydroazetes via Rh(II)-catalyzed reaction of diazoesters with trimethylsilyl-protected 2-(pyridin-2-yl)-2H-azirines},
journal = {Chemistry of Heterocyclic Compounds},
year = {2019},
volume = {55},
publisher = {Springer Nature},
month = {dec},
url = {https://doi.org/10.1007/s10593-019-02599-y},
number = {12},
pages = {1185--1189},
doi = {10.1007/s10593-019-02599-y}
}
Cite this
MLA
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Koronatov, Alexander N., et al. “One-pot synthesis of 3-(pyridin-2-yl)-2,3-dihydroazetes via Rh(II)-catalyzed reaction of diazoesters with trimethylsilyl-protected 2-(pyridin-2-yl)-2H-azirines.” Chemistry of Heterocyclic Compounds, vol. 55, no. 12, Dec. 2019, pp. 1185-1189. https://doi.org/10.1007/s10593-019-02599-y.