A facile carbene route to 2-fluoro-2-pyrrolines via fluorinated azomethine ylides
Publication type: Journal Article
Publication date: 2003-10-01
scimago Q3
wos Q3
SJR: 0.333
CiteScore: 3.7
Impact factor: 1.9
ISSN: 00221139, 18733328
Organic Chemistry
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Environmental Chemistry
Abstract
2-Fluoro-2-pyrrolines have been prepared by a domino reaction of difluorocarbene with N-substituted ketimines in the presence of fumaronitrile, malenitrile or dimethyl maleate, involving azomethine ylide formation, 1,3-dipolar cycloaddition, and dehydrofluorination. The reactions of 1H-dibenzo[b,e]azepine and 3,4-dihydroisoquinolines with difluorocarbene in the presence of fumaronitrile proceed with the formation of fluorinated 1H-dibenzo[c,f]pyrrolo[1,2-a]azepine and pyrrolo[2,1-a]isoquinoline derivatives. The yields of 2-fluoro-2-pyrrolines depend mostly on their resistance to chromatographic work-up and are higher for 5,5-disubstituted pyrrolines compared to 5-monosubstituted derivatives.
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GOST
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Novikov M. S., Shevchenko M. V., Khlebnikov A. F. A facile carbene route to 2-fluoro-2-pyrrolines via fluorinated azomethine ylides // Journal of Fluorine Chemistry. 2003. Vol. 123. No. 2. pp. 177-181.
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Novikov M. S., Shevchenko M. V., Khlebnikov A. F. A facile carbene route to 2-fluoro-2-pyrrolines via fluorinated azomethine ylides // Journal of Fluorine Chemistry. 2003. Vol. 123. No. 2. pp. 177-181.
Cite this
RIS
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TY - JOUR
DO - 10.1016/S0022-1139(03)00116-7
UR - https://doi.org/10.1016/S0022-1139(03)00116-7
TI - A facile carbene route to 2-fluoro-2-pyrrolines via fluorinated azomethine ylides
T2 - Journal of Fluorine Chemistry
AU - Novikov, Mikhail S.
AU - Shevchenko, Mikhail V.
AU - Khlebnikov, Alexander F
PY - 2003
DA - 2003/10/01
PB - Elsevier
SP - 177-181
IS - 2
VL - 123
SN - 0022-1139
SN - 1873-3328
ER -
Cite this
BibTex (up to 50 authors)
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@article{2003_Shevchenko,
author = {Mikhail S. Novikov and Mikhail V. Shevchenko and Alexander F Khlebnikov},
title = {A facile carbene route to 2-fluoro-2-pyrrolines via fluorinated azomethine ylides},
journal = {Journal of Fluorine Chemistry},
year = {2003},
volume = {123},
publisher = {Elsevier},
month = {oct},
url = {https://doi.org/10.1016/S0022-1139(03)00116-7},
number = {2},
pages = {177--181},
doi = {10.1016/S0022-1139(03)00116-7}
}
Cite this
MLA
Copy
Shevchenko, Mikhail V., et al. “A facile carbene route to 2-fluoro-2-pyrrolines via fluorinated azomethine ylides.” Journal of Fluorine Chemistry, vol. 123, no. 2, Oct. 2003, pp. 177-181. https://doi.org/10.1016/S0022-1139(03)00116-7.
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