Nonconcerted cycloaddition of 2H-azirines to acylketenes: A route to N-bridgehead heterocycles
Publication type: Journal Article
Publication date: 2011-10-18
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
21985422
Organic Chemistry
Abstract
Reactions of acylketenes, generated from diazo diketones, with 2-unsubstituted and 2-monosubstituted 3-aryl-2H-azirines lead to 1:1 or 2:1 adducts, which are derivatives of 5-oxa-1-azabicyclo[4.1.0]hept-3-ene or 5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene. According to DFT B3LYP/6-31G(d) computations, the formation of (4+2)-monoadducts proceeds via a stepwise non-pericyclic mechanism. Reaction with methanol transforms quantitatively both 1:1 and 2:1 adducts into 1,4-oxazepine derivatives.
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Total citations:
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GOST
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Khlebnikov A. F. et al. Nonconcerted cycloaddition of 2H-azirines to acylketenes: A route to N-bridgehead heterocycles // Journal of Organic Chemistry. 2011. Vol. 76. No. 22. pp. 9344-9352.
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Khlebnikov A. F., Novikov M. S., Pakalnis V. V., Yufit D. S. Nonconcerted cycloaddition of 2H-azirines to acylketenes: A route to N-bridgehead heterocycles // Journal of Organic Chemistry. 2011. Vol. 76. No. 22. pp. 9344-9352.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jo201563b
UR - https://doi.org/10.1021/jo201563b
TI - Nonconcerted cycloaddition of 2H-azirines to acylketenes: A route to N-bridgehead heterocycles
T2 - Journal of Organic Chemistry
AU - Khlebnikov, Alexander F
AU - Novikov, Mikhail S.
AU - Pakalnis, Viktoriia V
AU - Yufit, Dmitry S.
PY - 2011
DA - 2011/10/18
PB - American Chemical Society (ACS)
SP - 9344-9352
IS - 22
VL - 76
PMID - 21985422
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2011_Khlebnikov,
author = {Alexander F Khlebnikov and Mikhail S. Novikov and Viktoriia V Pakalnis and Dmitry S. Yufit},
title = {Nonconcerted cycloaddition of 2H-azirines to acylketenes: A route to N-bridgehead heterocycles},
journal = {Journal of Organic Chemistry},
year = {2011},
volume = {76},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/jo201563b},
number = {22},
pages = {9344--9352},
doi = {10.1021/jo201563b}
}
Cite this
MLA
Copy
Khlebnikov, Alexander F., et al. “Nonconcerted cycloaddition of 2H-azirines to acylketenes: A route to N-bridgehead heterocycles.” Journal of Organic Chemistry, vol. 76, no. 22, Oct. 2011, pp. 9344-9352. https://doi.org/10.1021/jo201563b.
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