Two-atom azirine ring expansion reaction of methyl 2-diazo-3-(4-methoxyphenyl)-3-oxopropanoate via a dirhodium tetraacetate-catalyzed Wolff rearrangement
Publication type: Journal Article
Publication date: 2017-09-01
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
Rh2(OAc)4-catalyzed Wolff rearrangement of methyl 2-diazo-3-(4-methoxyphenyl)-3-oxopropanoate gave methoxycarbonyl(4-methoxyphenyl) ketene that was added to 2Н-azirines, resulting in opening of the three-membered ring at the N–C(2) bond and leading to the formation of 3,4-dihydro-2Н-pyrrol-2-one derivatives. Depending on the structure of the obtained products, they isomerized to the more stable 1Н-pyrrol-2(3H)-one derivatives or added a water molecule at the C=N bond.
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Rostovskii N. V. et al. Two-atom azirine ring expansion reaction of methyl 2-diazo-3-(4-methoxyphenyl)-3-oxopropanoate via a dirhodium tetraacetate-catalyzed Wolff rearrangement // Chemistry of Heterocyclic Compounds. 2017. Vol. 53. No. 9. pp. 985-988.
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Rostovskii N. V., Novikov M. S., Khlebnikov A. F., Yufit D. S. Two-atom azirine ring expansion reaction of methyl 2-diazo-3-(4-methoxyphenyl)-3-oxopropanoate via a dirhodium tetraacetate-catalyzed Wolff rearrangement // Chemistry of Heterocyclic Compounds. 2017. Vol. 53. No. 9. pp. 985-988.
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TY - JOUR
DO - 10.1007/s10593-017-2160-3
UR - https://doi.org/10.1007/s10593-017-2160-3
TI - Two-atom azirine ring expansion reaction of methyl 2-diazo-3-(4-methoxyphenyl)-3-oxopropanoate via a dirhodium tetraacetate-catalyzed Wolff rearrangement
T2 - Chemistry of Heterocyclic Compounds
AU - Rostovskii, Nikolai V
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F
AU - Yufit, Dmitry S.
PY - 2017
DA - 2017/09/01
PB - Springer Nature
SP - 985-988
IS - 9
VL - 53
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2017_Rostovskii,
author = {Nikolai V Rostovskii and Mikhail S. Novikov and Alexander F Khlebnikov and Dmitry S. Yufit},
title = {Two-atom azirine ring expansion reaction of methyl 2-diazo-3-(4-methoxyphenyl)-3-oxopropanoate via a dirhodium tetraacetate-catalyzed Wolff rearrangement},
journal = {Chemistry of Heterocyclic Compounds},
year = {2017},
volume = {53},
publisher = {Springer Nature},
month = {sep},
url = {https://doi.org/10.1007/s10593-017-2160-3},
number = {9},
pages = {985--988},
doi = {10.1007/s10593-017-2160-3}
}
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Rostovskii, Nikolai V., et al. “Two-atom azirine ring expansion reaction of methyl 2-diazo-3-(4-methoxyphenyl)-3-oxopropanoate via a dirhodium tetraacetate-catalyzed Wolff rearrangement.” Chemistry of Heterocyclic Compounds, vol. 53, no. 9, Sep. 2017, pp. 985-988. https://doi.org/10.1007/s10593-017-2160-3.