Nucleophile-Induced Rearrangement of 2 H-Azirine-2-carbonyl Azides to 2-(1 H-Tetrazol-1-yl)acetic Acid Derivatives
Publication type: Journal Article
Publication date: 2021-08-12
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
34382398
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
2H-Azirine-2-carbonyl azides undergo a rearrangement into derivatives of 2-(1H-tetrazol-1-yl)acetic acid when interacting with O- and S-nucleophiles at room temperature. The reaction is catalyzed by tertiary amines or hydrazoic acid. The reaction with primary alcohols and phenols gives alkyl/aryl 2-(1H-tetrazol-1-yl)acetates. Thiophenols react with 2H-azirine-2-carbonyl azides to afford S-aryl 2-(1H-tetrazol-1-yl)ethanethioates. The mechanism of the nucleophile-induced rearrangement of 2H-azirine-2-carbonyl azides is discussed on the basis of DFT calculations as well as kinetic and 15N labeling experiments.
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12
Total citations:
12
Citations from 2024:
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(58%)
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Efimenko N. I. et al. Nucleophile-Induced Rearrangement of 2 H-Azirine-2-carbonyl Azides to 2-(1 H-Tetrazol-1-yl)acetic Acid Derivatives // Organic Letters. 2021. Vol. 23. No. 16. pp. 6362-6366.
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Efimenko N. I., Tomashenko O. A., Spiridonova D. V., Novikov M. S., Khlebnikov A. F. Nucleophile-Induced Rearrangement of 2 H-Azirine-2-carbonyl Azides to 2-(1 H-Tetrazol-1-yl)acetic Acid Derivatives // Organic Letters. 2021. Vol. 23. No. 16. pp. 6362-6366.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.1c02157
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.1c02157
TI - Nucleophile-Induced Rearrangement of 2 H-Azirine-2-carbonyl Azides to 2-(1 H-Tetrazol-1-yl)acetic Acid Derivatives
T2 - Organic Letters
AU - Efimenko, Nikita I
AU - Tomashenko, Olesya A
AU - Spiridonova, Darya V.
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F
PY - 2021
DA - 2021/08/12
PB - American Chemical Society (ACS)
SP - 6362-6366
IS - 16
VL - 23
PMID - 34382398
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2021_Efimenko,
author = {Nikita I Efimenko and Olesya A Tomashenko and Darya V. Spiridonova and Mikhail S. Novikov and Alexander F Khlebnikov},
title = {Nucleophile-Induced Rearrangement of 2 H-Azirine-2-carbonyl Azides to 2-(1 H-Tetrazol-1-yl)acetic Acid Derivatives},
journal = {Organic Letters},
year = {2021},
volume = {23},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.1c02157},
number = {16},
pages = {6362--6366},
doi = {10.1021/acs.orglett.1c02157}
}
Cite this
MLA
Copy
Efimenko, Nikita I., et al. “Nucleophile-Induced Rearrangement of 2 H-Azirine-2-carbonyl Azides to 2-(1 H-Tetrazol-1-yl)acetic Acid Derivatives.” Organic Letters, vol. 23, no. 16, Aug. 2021, pp. 6362-6366. https://pubs.acs.org/doi/10.1021/acs.orglett.1c02157.