Royal Society of Chemistry (RSC)
Organic Chemistry Frontiers
,  volume 12 ,  issue 7 ,  pages 2187-2193

Cyclopropanation vs. single-carbon insertion of pyrrole-2,3-diones with sulfonium ylides: synthesis of functionalized 2-azabicyclo[3.1.0]hexanes and pyridine-2,3-diones

Publication type: Journal Article
Publication date: 2025-01-28
Royal Society of Chemistry (RSC)
scimago Q1
wos Q1
SJR: 1.068
CiteScore: 8.2
Impact factor: 4.7
ISSN: 20524110, 20524129
Abstract
The method for the diastereoselective synthesis of pyrrole-annulated donor–acceptor cyclopropanes from pyrrole-2,3-diones and stabilized sulfonium ylides has been developed. Ring opening of these annulated cyclopropanes (spontaneous or Lewis acid/thermal mediated) leads to functionalized pyridine-2,3-diones with good yields and high functional group tolerance. The ring expansion of pyrrole-2,3-diones to pyridine-2,3-diones via sulfonium ylide insertion can be performed in a one-pot manner without isolation of the intermediate cyclopropane.
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Muranova M. M. et al. Cyclopropanation vs. single-carbon insertion of pyrrole-2,3-diones with sulfonium ylides: synthesis of functionalized 2-azabicyclo[3.1.0]hexanes and pyridine-2,3-diones // Organic Chemistry Frontiers. 2025. Vol. 12. No. 7. pp. 2187-2193.
GOST all authors (up to 50) Copy
Muranova M. M., Galeev A. R., Maslivets A. N., Dmitriev M. V. Cyclopropanation vs. single-carbon insertion of pyrrole-2,3-diones with sulfonium ylides: synthesis of functionalized 2-azabicyclo[3.1.0]hexanes and pyridine-2,3-diones // Organic Chemistry Frontiers. 2025. Vol. 12. No. 7. pp. 2187-2193.
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TY - JOUR
DO - 10.1039/d4qo02337d
UR - http://pubs.rsc.org/en/Content/ArticleLanding/2025/QO/D4QO02337D
TI - Cyclopropanation vs. single-carbon insertion of pyrrole-2,3-diones with sulfonium ylides: synthesis of functionalized 2-azabicyclo[3.1.0]hexanes and pyridine-2,3-diones
T2 - Organic Chemistry Frontiers
AU - Muranova, Maria M.
AU - Galeev, Andrew R
AU - Maslivets, Andrey N.
AU - Dmitriev, Maksim V
PY - 2025
DA - 2025/01/28
PB - Royal Society of Chemistry (RSC)
SP - 2187-2193
IS - 7
VL - 12
SN - 2052-4110
SN - 2052-4129
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2025_Muranova,
author = {Maria M. Muranova and Andrew R Galeev and Andrey N. Maslivets and Maksim V Dmitriev},
title = {Cyclopropanation vs. single-carbon insertion of pyrrole-2,3-diones with sulfonium ylides: synthesis of functionalized 2-azabicyclo[3.1.0]hexanes and pyridine-2,3-diones},
journal = {Organic Chemistry Frontiers},
year = {2025},
volume = {12},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {http://pubs.rsc.org/en/Content/ArticleLanding/2025/QO/D4QO02337D},
number = {7},
pages = {2187--2193},
doi = {10.1039/d4qo02337d}
}
MLA
Cite this
MLA Copy
Muranova, Maria M., et al. “Cyclopropanation vs. single-carbon insertion of pyrrole-2,3-diones with sulfonium ylides: synthesis of functionalized 2-azabicyclo[3.1.0]hexanes and pyridine-2,3-diones.” Organic Chemistry Frontiers, vol. 12, no. 7, Jan. 2025, pp. 2187-2193. http://pubs.rsc.org/en/Content/ArticleLanding/2025/QO/D4QO02337D.