European Journal of Organic Chemistry, volume 2012, issue 10, pages 2054-2061
Cycloaddition of C,C-Disubstituted Ketonitrones with Acceptor Methylenecyclopropanes and Subsequent Rearrangement Cascade of 5-Spirocyclopropane-isoxazolidines
Publication type: Journal Article
Publication date: 2012-02-24
Q2
Q2
SJR: 0.584
CiteScore: 5.4
Impact factor: 2.5
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
A new reaction cascade to give tricyclic cores of 2,4-dihydro-1H-azeto[1,2-a]quinolines (benzocarbacephems) and pyrrolo[1,2-a]quinolines starting from acyclic N-aryl ketonitrones and acceptor ring substituted methylenecyclopropanes has been reported. This reaction includes 1,3-dipolar cycloaddition of N-aryl-C,C-diaryl or N-aryl-C,C-bis(methoxycarbonyl) nitrones 1 to the double bond of dimethyl methylenecyclopropane-1,2-dicarboxylate 2 or benzylidenecyclopropane-1,1-dicarboxylate 3, followed by Brandi–Guarna rearrangement of the initially formed 5-spirocyclopropane-isoxazolidine cycloadducts to give 2,4-dihydro-1H-azeto[1,2-a]quinolines 4 or pyrrolo[1,2-a]quinolines 6.
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GOST
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Tran T. Q. et al. Cycloaddition of C,C-Disubstituted Ketonitrones with Acceptor Methylenecyclopropanes and Subsequent Rearrangement Cascade of 5-Spirocyclopropane-isoxazolidines // European Journal of Organic Chemistry. 2012. Vol. 2012. No. 10. pp. 2054-2061.
GOST all authors (up to 50)
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Tran T. Q., Diev V. V., Starova G. L., Gurzhiy V. V., Molchanov A. P. Cycloaddition of C,C-Disubstituted Ketonitrones with Acceptor Methylenecyclopropanes and Subsequent Rearrangement Cascade of 5-Spirocyclopropane-isoxazolidines // European Journal of Organic Chemistry. 2012. Vol. 2012. No. 10. pp. 2054-2061.
Cite this
RIS
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TY - JOUR
DO - 10.1002/ejoc.201200039
UR - https://doi.org/10.1002/ejoc.201200039
TI - Cycloaddition of C,C-Disubstituted Ketonitrones with Acceptor Methylenecyclopropanes and Subsequent Rearrangement Cascade of 5-Spirocyclopropane-isoxazolidines
T2 - European Journal of Organic Chemistry
AU - Tran, Tung Q
AU - Diev, Vyacheslav V
AU - Starova, G. L.
AU - Gurzhiy, Vladislav V.
AU - Molchanov, Alexander P.
PY - 2012
DA - 2012/02/24
PB - Wiley
SP - 2054-2061
IS - 10
VL - 2012
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2012_Tran,
author = {Tung Q Tran and Vyacheslav V Diev and G. L. Starova and Vladislav V. Gurzhiy and Alexander P. Molchanov},
title = {Cycloaddition of C,C-Disubstituted Ketonitrones with Acceptor Methylenecyclopropanes and Subsequent Rearrangement Cascade of 5-Spirocyclopropane-isoxazolidines},
journal = {European Journal of Organic Chemistry},
year = {2012},
volume = {2012},
publisher = {Wiley},
month = {feb},
url = {https://doi.org/10.1002/ejoc.201200039},
number = {10},
pages = {2054--2061},
doi = {10.1002/ejoc.201200039}
}
Cite this
MLA
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Tran, Tung Q., et al. “Cycloaddition of C,C-Disubstituted Ketonitrones with Acceptor Methylenecyclopropanes and Subsequent Rearrangement Cascade of 5-Spirocyclopropane-isoxazolidines.” European Journal of Organic Chemistry, vol. 2012, no. 10, Feb. 2012, pp. 2054-2061. https://doi.org/10.1002/ejoc.201200039.