Ring Opening of Donor-Acceptor Cyclopropanes with the Azide Ion: A Tool for Construction of N-Heterocycles
Publication type: Journal Article
Publication date: 2015-01-08
scimago Q1
wos Q2
SJR: 0.981
CiteScore: 6.7
Impact factor: 3.7
ISSN: 09476539, 15213765
PubMed ID:
25573783
General Chemistry
Catalysis
Organic Chemistry
Abstract
A general method for ring opening of various donor-acceptor cyclopropanes with the azide ion through an SN 2-like reaction has been developed. This highly regioselective and stereospecific process proceeds through nucleophilic attack on the more-substituted C2 atom of a cyclopropane with complete inversion of configuration at this center. Results of DFT calculations support the SN 2 mechanism and demonstrate good qualitative correlation between the relative experimental reactivity of cyclopropanes and the calculated energy barriers. The reaction provides a straightforward approach to a variety of polyfunctional azides in up to 91 % yield. The high synthetic utility of these azides and the possibilities of their involvement in diversity-oriented synthesis were demonstrated by the developed multipath strategy of their transformations into five-, six-, and seven-membered N-heterocycles, as well as complex annulated compounds, including natural products and medicines such as (-)-nicotine and atorvastatin.
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Total citations:
150
Citations from 2025:
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GOST
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Konstantin V. I. et al. Ring Opening of Donor-Acceptor Cyclopropanes with the Azide Ion: A Tool for Construction of N-Heterocycles // Chemistry - A European Journal. 2015. Vol. 21. No. 13. pp. 4975-4987.
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Konstantin V. I., Villemson E. V., Budynina E. M., Ivanova O., Trushkov I. V., Melnikov M. Y. Ring Opening of Donor-Acceptor Cyclopropanes with the Azide Ion: A Tool for Construction of N-Heterocycles // Chemistry - A European Journal. 2015. Vol. 21. No. 13. pp. 4975-4987.
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RIS
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TY - JOUR
DO - 10.1002/chem.201405551
UR - https://doi.org/10.1002/chem.201405551
TI - Ring Opening of Donor-Acceptor Cyclopropanes with the Azide Ion: A Tool for Construction of N-Heterocycles
T2 - Chemistry - A European Journal
AU - Konstantin, V. Ivanov
AU - Villemson, Elena V
AU - Budynina, Ekaterina M
AU - Ivanova, Olga
AU - Trushkov, Igor V
AU - Melnikov, Mikhail Y.
PY - 2015
DA - 2015/01/08
PB - Wiley
SP - 4975-4987
IS - 13
VL - 21
PMID - 25573783
SN - 0947-6539
SN - 1521-3765
ER -
Cite this
BibTex (up to 50 authors)
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@article{2015_Konstantin,
author = {V. Ivanov Konstantin and Elena V Villemson and Ekaterina M Budynina and Olga Ivanova and Igor V Trushkov and Mikhail Y. Melnikov},
title = {Ring Opening of Donor-Acceptor Cyclopropanes with the Azide Ion: A Tool for Construction of N-Heterocycles},
journal = {Chemistry - A European Journal},
year = {2015},
volume = {21},
publisher = {Wiley},
month = {jan},
url = {https://doi.org/10.1002/chem.201405551},
number = {13},
pages = {4975--4987},
doi = {10.1002/chem.201405551}
}
Cite this
MLA
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Konstantin, V. Ivanov, et al. “Ring Opening of Donor-Acceptor Cyclopropanes with the Azide Ion: A Tool for Construction of N-Heterocycles.” Chemistry - A European Journal, vol. 21, no. 13, Jan. 2015, pp. 4975-4987. https://doi.org/10.1002/chem.201405551.